37,298 results for "Florida Keys waterfront"

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Pensacola Beach front Condo Gulf Breeze, Florida

Pensacola Beach front Condo

Located in Gulf Breeze, Florida, United States. Pensacola Beach front Condo Emerald Waters Condo, 1Br 1.5 Bath, Sleeps 7 invites you to relax and rejuvenate in this family friendly, beach front 2nd floor condo, with emerald blue waters, sugar white sandy beaches, at your doorstep. Endless water views, close enough to reach out n touch from the comfort this condo. Fully equipped, designated garage parking, Free wifi, newly renovated pool. Great seafood restaurant, and 24 hr conv. store across the street. All brand new S.S. appliances. Local attractions, dining, a short 5 min drive, or a relaxing walk or bike on local beach trails

🛏 1 bed · 👥 7 guests
$141 /night
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Entire condo in the heart of Pensacola Beach across from the Gulf Pensacola Beach, Florida

Entire condo in the heart of Pensacola Beach across from the Gulf

Located in Pensacola Beach, Florida, United States. Entire condo in the heart of Pensacola Beach across from the Gulf This 10th floor condo unit is just steps to the Gulf and all the best restaurants. The master bedroom features a king size bed, spacious vanity off of the master bath. The second bedroom hosts a queen size bed. Relax in the outdoor pool after a long day at the beach, followed by a nice dinner out or just staying in and cooking in the fully equipped kitchen. Enjoy breathtaking views of the Gulf and fabulous sunsets from the private balcony. A washer and dryer is located in the condo for your convenience.

🛏 2 beds · 👥 4 guests
$381 /night
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Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views Islamorada, Florida

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

Located in Islamorada, Florida, United States. Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views We privately own a total of 5 boutique vacation rentals in Islamorada:VRBO listing #1576833 (5 bedroom)VRBO listing #1054019 (5 bedroom)VRBO listing #1977457 (7 bedroom)VRBO listing #3363008 (6 bedroom)VRBO listing #689629 (5 bedroom)Gorgeous 30’ oceanfront heated pool. House on an exceptionally private, natural beach and oceanfront seawall in Islamorada - observation dock for paddle boarding, fishing and kayaking. Property is flanked by natural preserve on one side and has wide open expansive ocean views. The private beach is located along a wildlife protected turtle nesting beach that left natural for turtle nesting season. There is an incredible 180 degree water view from almost every room in the house. Spectacular sunrises flood the rooms with golden light reflected off the ocean. The sun rises over the water every morning within your view. The sunsets are equally stunning over the peninsula leav

🛏 5 beds · 👥 10 guests
$914 /night
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Isla Kiwi: Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada, Florida

Isla Kiwi: Waterfront Boutique Resort, Htd Pool, Dock, Walkable

Located in Islamorada, Florida, United States. Isla Kiwi: Waterfront Boutique Resort, Htd Pool, Dock, Walkable Short Description🏡 Community amenities: heated pool, boat dock, BBQ📍Walk to shops, grocery store, parks, restaurants🛏️ All bedrooms feature ensuite bathroom 🐶 Dog friendly 🤝 24/7 Guest supportIsla Kiwi (Villa #2) is part of Little Basin Villas upscale community of nine luxury vacation villas, located in the heart of the Art District of Islamorada. Boasting a bayside boat dock and private community pool, our villa offers the perfect blend of relaxation and adventure. Enjoy breathtaking sunsets, waterfront views and island décor & foliage. It uniquely offers three bedrooms complete with their own ensuite bathroom, plus a half bath. It is fully furnished, and offers a private deck, and a top balcony with partial water view. This home is fully stocked with everything you need, and a full time Guest Experience Team to assist in making the most of your stay. The Space🛋️ Living Room: Open-concept living area that features ample

🛏 3 beds · 👥 6 guests
$325 /night
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Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,   Islamorada, Florida

Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,

Located in Islamorada, Florida, United States. Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis, “Ocean Breeze” – This Beautiful Condominium Features an Ocean view, Protected Boat Slip, Tennis, Gym, and much, much more. This 2 Bedroom condo at Bay Harbour sleeps 4 adults & two children 6 and under. Easy access to the Gulf or Ocean makes this the perfect home port for any fishing vacation. Bring your own boat or rent from any of the many boat rental companies in the area. If your vacation is more about relaxation, then kick back at one of the near-by beautiful sandy beaches. Nested within the gated community of Bay Harbour luxury condominiums, this unit will provide the ultimate base camp for the family to wind down after a day of fishing. Two large bedrooms with private bathrooms plus a sleeper-sofa with half bath can accommodate a family of six or two couples very comfortably. The living room has brand new island style furniture and a 65” LCD TV for those movie nights or football watching days! The che

🛏 2 beds · 👥 4 guests
$240 /night
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Malayan Palm North 2 Bedrooms, 1 Bath, Garden View Islamorada, Florida

Malayan Palm North 2 Bedrooms, 1 Bath, Garden View

Located in Islamorada, Florida, United States. Malayan Palm North 2 Bedrooms, 1 Bath, Garden View Poolside,2 Queen Beds,1 Pull OutResort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.Guests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.The Malayan Palm has the option of opening a locked interior door, combining the space into a 3 bedroom, 2 bath home.

🛏 2 beds · 👥 6 guests
$366 /night
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Beautiful Waterfront Port Antigua Home, Pool, Private Beach Islamorada, Florida

Beautiful Waterfront Port Antigua Home, Pool, Private Beach

Located in Islamorada, Florida, United States. Beautiful Waterfront Port Antigua Home, Pool, Private Beach Stunning two-story, 3-bedroom resort-style, professionally decorated home. Inside, you'll find a modern and welcoming home with tiled floors, comfortable furniture, and lots of attractive décor and personal touches. The beautiful, modern kitchen has stainless steel appliances. The center island is great to prepare wonderful meals. The incredible kitchen is fully equipped and has a fabulous view out the window. Enjoy your meals at the dining room table with seating for six with gorgeous water views. The three large bedrooms are all furnished with king size beds. The main suite has a large walk-in shower and a separate jetted tub. Want to sleep in late? The main suite has black-out curtains! Relax and enjoy the canal view while sipping your morning coffee or tea from the main bedroom’s screened-in balcony. Walk out to your tropical paradise. The home is professionally landscaped providing privacy for your enjoyment while relaxin

🛏 3 beds · 👥 6 guests
$366 /night
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The Bonefish House at Tarpon Point Islamorada, Florida

The Bonefish House at Tarpon Point

Located in Islamorada, Florida, United States. The Bonefish House at Tarpon Point Introducing the "Bonefish House," at Tarpon Point!This opulent, luxury, home is equipped to accommodate eight adults with 4 bedrooms & 4 full bathrooms. The open living space offers easy entertaining and direct panoramic views of the community pool and Atlantic Ocean. The well-appointed and fully equipped chef’s kitchen offers the finest high-end appliances to satisfy everyone’s culinary needs. Whether you are cooking for two or eight, there is plenty of room for everyone to have a seat at the table. Or, eat al fresco right off the main level balcony and enjoy the balmy ocean breeze. The integrated Sonos system offers the ultimate wireless home sound system that streams off the house WiFi network and fills the home with brilliant sound.  This sought after gated community boasts beautifully landscaped grounds, oceanfront pool with heater and chiller, 420 feet of ocean frontage, an observation dock you can fish from, and a beach area where you can launc

🛏 4 beds · 👥 8 guests
$660 /night
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🌊MOTHER OCEAN🌊 Islamorada Condo w/ Dockage & Ocean Views! Islamorada, Florida

🌊MOTHER OCEAN🌊 Islamorada Condo w/ Dockage & Ocean Views!

Located in Islamorada, Florida, United States. 🌊MOTHER OCEAN🌊 Islamorada Condo w/ Dockage & Ocean Views! Welcome to Mother Ocean! This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfect for a family or group of friends. It features modern amenities and coastal decor throughout, providing a comfortable and inviting atmosphere for your stay. The spacious living room offers captivating views of the ocean, and opens up to a large screened-in balcony where you can enjoy watching the morning sunrise or spot manatees in the afternoon. The fully equipped kitchen comes with a few extra features such as a coffee bar, air fryer oven and bar seating. The master bedroom has a king-sized bed and its own private bathroom that boasts a walk-in shower, jetted tub, double vanity sinks and a water closet. The second and third bedrooms offer queen and twin sized beds and share a full bathroom. Other amenities include a washer and dryer, central air conditioning, cable TV, and high-speed internet throughout. The c

🛏 3 beds · 👥 6 guests
$267 /night
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Coastal Elegance Near Theater of the Sea! 2 Stylish Villas, Kitchen, Bayfront! Islamorada, Florida

Coastal Elegance Near Theater of the Sea! 2 Stylish Villas, Kitchen, Bayfront!

Located in Islamorada, Florida, United States. Coastal Elegance Near Theater of the Sea! 2 Stylish Villas, Kitchen, Bayfront! Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and bustle. Step outside your door and be greeted by the breathtaking beauty of our private beach. Feel the soft sand between your toes as you stroll along the shoreline or soak up the sun on a beach lounger. For those seeking adventure, indulge in various water sports activities nearby, such as kayaking or paddle boarding, Our newly renovated resort boasts an array of amenities to enhance your experience. Take a dip in our sparkling outdoor pool, surrounded by lush tropical gardens. Our friendly staff is always ready to provide recommendations and assist you in planning memorable excursions. Experience the epitome of coastal elegance and create timeless memories at our exclusive retreat. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typ

🛏 4 beds · 👥 10 guests
$731 /night
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The Snook House ~ 4 Bed / 4 Bath Luxury Oceanfront Home in Islamorada! Islamorada, Florida

The Snook House ~ 4 Bed / 4 Bath Luxury Oceanfront Home in Islamorada!

Located in Islamorada, Florida, United States. The Snook House ~ 4 Bed / 4 Bath Luxury Oceanfront Home in Islamorada! This impressive home is tastefully decorated and features an open floor plan, soaring ceilings, an unimpeded, nearly 180 degrees of breathtaking ocean vistas and four oversized bedrooms, each with their own bathroom. On the main level, you will find the fully appointed chef’s kitchen which includes the finest high-end appliances to satisfy everyone’s culinary needs, a full size washer and dryer, dining area, and spacious living area that’s leads out to the oceanfront balcony with additional seating for morning coffee, happy hour or dinner al fresco. Don't forget about the covered patio downstairs that is only feet away from the ocean and includes a Weber gas grill and a teak dining table for eight. This is the perfect location to escape from the potent Florida sun, while still being able to enjoy the glistening ocean and balmy breeze.The spacious master bedroom is equipped with a king sized bed and private balcony

🛏 4 beds · 👥 8 guests
$650 /night
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Island Time:  1BR with Den and Two Balconies Islamorada, Florida

Island Time: 1BR with Den and Two Balconies

Located in Islamorada, Florida, United States. Island Time: 1BR with Den and Two Balconies Indulge in the spacious layout featuring a well-appointed kitchen complete with a full-sized fridge, stove, coffee maker, toaster, and all the necessary dishes and silverware. Unwind in the welcoming living room, furnished with a sofa bed and dining table, while the balcony beckons with invigorating tropical breezes. A convenient bathroom rounds out the main living space.The bedroom provides a tranquil sanctuary with a luxurious queen bed and access to a den furnished with a full-sized sleeper sofa, perfect for extra guests or a cozy reading nook. The bedroom also boasts an ensuite bath, and the den opens onto a second balcony. Please note that while our property enjoys an oceanfront setting, not all units offer direct views of the ocean.Explore the wealth of amenities at Caloosa Cove Resort and Marina, including a heated pool, beach access, the Safari Lounge, a General Store, and complimentary Wi-Fi. Dive into aquatic adventures with Charte

🛏 1 bed · 👥 6 guests
$216 /night
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Isla Mirabelle: Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada, Florida

Isla Mirabelle: Waterfront Boutique Resort, Htd Pool, Dock, Walkable

Located in Islamorada, Florida, United States. Isla Mirabelle: Waterfront Boutique Resort, Htd Pool, Dock, Walkable Short Description🏡 Community amenities: heated pool, boat dock, BBQ📍Walk to shops, grocery store, parks, restaurants🛏️ All bedrooms feature ensuite bathroom 🤝 24/7 Guest supportIsla Mirabelle (Villa #7) is part of Little Basin Villas upscale community of nine luxury vacation villas, located in the heart of the Art District of Islamorada. Boasting a bayside boat dock and private community pool, our villa offers the perfect blend of relaxation and adventure. Enjoy breathtaking sunsets, waterfront views and island décor & foliage. It uniquely offers three bedrooms complete with their own ensuite bathroom, plus a half bath. It is fully furnished, and offers a private deck, and a top balcony. This home is fully stocked with everything you need, and a full time Guest Experience Team to assist in making the most of your stay. The Space🛋️ Living Room: Open-concept living area that features ample seating w/ sectional sofas, m

🛏 3 beds · 👥 6 guests
$321 /night
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This oceanfront condo is absolutely beautiful. Islamorada, Florida

This oceanfront condo is absolutely beautiful.

Located in Islamorada, Florida, United States. This oceanfront condo is absolutely beautiful. PROPERTY NAME: The Palms #31379901 Overseas Highway, Islamorada, FLLOCATION: Bayside Condominium MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 79.9DETAILS: Spectacular oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Alligator Reef Lighthouse is easily visible from your master suite or the balcony and you'll be able to watch cruise ships as they pass by the reef and adventure seekers as they paddle their paddle boards or kayaks directly in the waters in front of your unit. This comfortably furnished condo offers flat screen TV in the living area. The Palms is conveniently located near fishing charter opportunities, Bud 'n Mary's Marina and Dive Shop, world-class dining, the Islamorada Art District, tourist attractions and shopping. The condo complex features a pool, hot tub, men's and women's exercise rooms, community

🛏 2 beds · 👥 5 guests
$126 /night
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Yolo " You only live once" - Fishing Paradise in Islamorada with a 70ft Dock!!!! Islamorada, Florida

Yolo " You only live once" - Fishing Paradise in Islamorada with a 70ft Dock!!!!

Located in Islamorada, Florida, United States. Yolo " You only live once" - Fishing Paradise in Islamorada with a 70ft Dock!!!! 1440 sf - 2 BedroomsSleeps 4 adults (also includes xtra bed in guest room plus EZ-Bed electric queen Bed and large sectional couch with chaise lounge and cuddler for larger families).Fully renovated and updated in 2021.70ft foot dock and cleaning table.Great ambience, quiet home like feel.Private community beach with beautiful sunsets.Located at White Marlin BeachIslamorada MM74SPORT FISHING CAPITAL OF THE WORLD. Just minutes from Channel 2 bridge known for excellent tarpon, snapper, and other great inshore fishing: as well as the Channel 5 bridge with open access to blue water for awesome offshore fun like Sailfish, Marlin, Mahi, Mutton, Yellow tail and deep drop fishing at your fingertips. If Bone fishing and other flats fishing is what your after, you won’t be disappointed with Florida Bay at your doorstep. This home is smack in the middle of it all.SNORKELING is a no brainer in the Islamorada crystal-c

🛏 2 beds · 👥 6 guests
$233 /night
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Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views! Islamorada, Florida

Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views!

Located in Islamorada, Florida, United States. Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views! Short Description🏡 Community amenities: heated pool, boat dock, BBQ📍Walk to shops, grocery store, parks, restaurants🛏️ All bedrooms feature ensuite bathroom 🤝 24/7 Guest supportBayberry Key (Villa #9) is part of Little Basin Villas upscale community of nine luxury vacation villas, located in the heart of the Art District of Islamorada. This is the only Villa that offers an unobstructed water view from the private outdoor terrace and balcony! Boasting a bayside boat dock and private community pool, our villa offers the perfect blend of relaxation and adventure. Enjoy breathtaking sunsets, waterfront views and island décor & foliage. It uniquely offers three bedrooms complete with their own ensuite bathroom, plus a half bath. It is completely furnished and stocked with the essentials needed for an amazing and comfortable vacation. You also have access to our concierge, Guest Experience Team to assist in making the

🛏 3 beds · 👥 6 guests
$380 /night
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Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool Islamorada, Florida

Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool

Located in Islamorada, Florida, United States. Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical resid

🛏 3 beds · 👥 12 guests
$1,395 /night
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Voted best boutique resort in Islamorada! Beach, dockage, pool + more! Islamorada, Florida

Voted best boutique resort in Islamorada! Beach, dockage, pool + more!

Located in Islamorada, Florida, United States. Voted best boutique resort in Islamorada! Beach, dockage, pool + more! Located in the heart of Islamorada, Mermaid’s Bay Boutique Estate is a secluded oasis situated directly on the bay. Secured by a gated entrance, the property sprawls over 3.5 meticulously maintained acres, with over 300 feet of bay frontage, protected dockage, and a resort-style pool and hot tub.Nestled within one captivating property, our collection of vacation rentals at Mermaid's Bay includes three individual homes, each with their own allure and privacy. The homes may be rented individually or collectively and are available for weekly or longer rentals. (Note: This listing is for booking the entire property. Each unit has its own listing for individual bookings.)The primary home (4 bedrooms, 6 bathrooms) on the property is spacious and perfectly suited for larger families or groups of friends. Two cottages (each with 2 bedrooms and 1 bathroom) are also located on the property, and provide a great option for smal

🛏 8 beds · 👥 22 guests
$2,088 /night
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Luxury Oceanfront Estate in Islamorada - Your Tropical Paradise Awaits! Islamorada, Florida

Luxury Oceanfront Estate in Islamorada - Your Tropical Paradise Awaits!

Located in Islamorada, Florida, United States. Luxury Oceanfront Estate in Islamorada - Your Tropical Paradise Awaits! Welcome to Orchid Beach, your ultimate oceanside escape! Nestled directly on the beach, this gated estate greets you with vibrant orchids woven into tropical landscaping, leading to an impressive waterfront home. Offering a unique getaway, the estate provides the perfect blend of togetherness and privacy with living accommodations spread across three distinct pods.The main living pod serves as the estate's heart, featuring a spacious, beautifully appointed living area, a fully equipped gourmet kitchen, a dining space, and an office loft. Large windows and French doors offer stunning ocean views and seamless indoor-outdoor living. The master suite pod is a secluded haven with a king-sized bed, en-suite bathroom, and private terrace. Wake up to a sunrise view over the ocean without leaving your bed. For groups of friends or families, the guest pod includes three guest rooms, each with its own entrance and en-suite ba

🛏 4 beds · 👥 8 guests
$961 /night
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Beautiful unit in one of the most prestigious Condo Complex in Islamorada Islamorada, Florida

Beautiful unit in one of the most prestigious Condo Complex in Islamorada

Located in Islamorada, Florida, United States. Beautiful unit in one of the most prestigious Condo Complex in Islamorada PROPERTY NAME: Beacon Reef #30183201 Old Highway, Islamorada, FloridaLOCATION: Ocean side CondoMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 83.2DETAILS: Fully renovated condo that offers inspiring tropical views including the ocean from the open-air balcony accessed from the main living area and the master bedroom suite. This charming, clean, spacious 2 bedroom 2 bath condo has all the comforts for a wonderful vacation. Furnishings have been updated and new items are being added frequently. This unit is located in one of the most desirable complexes in Islamorada. Its central location provides convenient access to everything Islamorada has to offer - world class diving, fishing, and restaurants. If you are feeling adventuresome, snorkel or scuba dive in the crystal clear sea or take a fishing charter to some of the best fishing spots in the world. If you

🛏 2 beds · 👥 4 guests
$109 /night
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Sun, Sand, and Relaxation Awaits! Ocean View Accommodation w/ Private Patio! Islamorada, Florida

Sun, Sand, and Relaxation Awaits! Ocean View Accommodation w/ Private Patio!

Located in Islamorada, Florida, United States. Sun, Sand, and Relaxation Awaits! Ocean View Accommodation w/ Private Patio! Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical reside

🛏 1 bed · 👥 4 guests
$533 /night
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Canary Island Palm North Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out Islamorada, Florida

Canary Island Palm North Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out

Located in Islamorada, Florida, United States. Canary Island Palm North Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out Poolside,1 King Bed, 2 QueenBeds, 1 Pull OutResort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.Guests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

🛏 2 beds · 👥 8 guests
$405 /night
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Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin! Islamorada, Florida

Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin!

Located in Islamorada, Florida, United States. Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin! Oceanfront property offering a unique experience for your tropical escape with views of both Islamorada Sandbar and Alligator Lighthouse! This rental can be separated into two distinct units, each equipped with its own full kitchen, bedroom, and bathroom. Embrace the laid-back atmosphere as you lounge at this property's shared pool with your favorite book or sip on a cool drink.For those with a passion for boating, you'll love the private boat basin right on the property with space to accommodate a boat up to 24 feet. You can easily explore the crystal-clear waters of the surrounding area or embark on a fishing adventure or explore the famous Islamorada Sandbar. Whether you're grilling up fresh seafood on the outdoor barbecue grill, enjoying a family movie night in the living room, or savoring a meal together at the dining table, every moment spent here is sure to create lasting memories.

🛏 2 beds · 👥 3 guests
$209 /night
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Remodeled Stilt home with Ocean Views Islamorada, Florida

Remodeled Stilt home with Ocean Views

Located in Islamorada, Florida, United States. Remodeled Stilt home with Ocean Views PROPERTY NAME: Blue Water Retreat137 Ocean Lane, Islamorada, FloridaLOCATION: Oceanside Canal home located in Lower Matecumbe, IslamoradaMINIMUM: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 76.3DETAILS: This home has it all - ocean side Lower Matecumbe location, remodeled in 2009 and 2022. Relax by the splash pool or sunbathe on the roof top and enjoy the spectacular views. There are blue water ocean views from almost every room in this home. This home is located on a canal front lot, offers dockage for a boat up to 30' with easy access to the ocean - a straight shot of about 200 yards to open water from the dock. The wrap-around screened balcony provides a respite after a day on the water. Take a dip in the pool and enjoy some afternoon refreshment. Grill your day's catch on the gas grill and dine at home or take it to one of our many fine local restaurants and let the chef cook it to your specificati

🛏 3 beds · 👥 6 guests
$327 /night
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Pensacola Beach front Condo

Gulf Breeze, Florida

Pensacola Beach front Condo

🛏 1 bed · 👥 7 guests

Located in Gulf Breeze, Florida, United States. Pensacola Beach front Condo Emerald Waters Condo, 1Br 1.5 Bath, Sleeps 7 invites you to relax and rejuvenate in this family friendly, beach front 2nd floor condo, with emerald blue waters, sugar white sandy beaches, at your doorstep. Endless water views, close enough to reach out n touch from the comfort this condo. Fully equipped, designated garage parking, Free wifi, newly renovated pool. Great seafood restaurant, and 24 hr conv. store across the street. All brand new S.S. appliances. Local attractions, dining, a short 5 min drive, or a relaxing walk or bike on local beach trails

$141

/ night

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Entire condo in the heart of Pensacola Beach across from the Gulf

Pensacola Beach, Florida

Entire condo in the heart of Pensacola Beach across from the Gulf

🛏 2 bed · 👥 4 guests

Located in Pensacola Beach, Florida, United States. Entire condo in the heart of Pensacola Beach across from the Gulf This 10th floor condo unit is just steps to the Gulf and all the best restaurants. The master bedroom features a king size bed, spacious vanity off of the master bath. The second bedroom hosts a queen size bed. Relax in the outdoor pool after a long day at the beach, followed by a nice dinner out or just staying in and cooking in the fully equipped kitchen. Enjoy breathtaking views of the Gulf and fabulous sunsets from the private balcony. A washer and dryer is located in the condo for your convenience.

$381

/ night

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Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

Islamorada, Florida

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

🛏 5 bed · 👥 10 guests

Located in Islamorada, Florida, United States. Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views We privately own a total of 5 boutique vacation rentals in Islamorada:VRBO listing #1576833 (5 bedroom)VRBO listing #1054019 (5 bedroom)VRBO listing #1977457 (7 bedroom)VRBO listing #3363008 (6 bedroom)VRBO listing #689629 (5 bedroom)Gorgeous 30’ oceanfront heated pool. House on an exceptionally private, natural beach and oceanfront seawall in Islamorada - observation dock for paddle boarding, fishing and kayaking. Property is flanked by natural preserve on one side and has wide open expansive ocean views. The private beach is located along a wildlife protected turtle nesting beach that left natural for turtle nesting season. There is an incredible 180 degree water view from almost every room in the house. Spectacular sunrises flood the rooms with golden light reflected off the ocean. The sun rises over the water every morning within your view. The sunsets are equally stunning over the peninsula leav

$914

/ night

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Isla Kiwi: Waterfront Boutique Resort, Htd Pool, Dock, Walkable

Islamorada, Florida

Isla Kiwi: Waterfront Boutique Resort, Htd Pool, Dock, Walkable

🛏 3 bed · 👥 6 guests

Located in Islamorada, Florida, United States. Isla Kiwi: Waterfront Boutique Resort, Htd Pool, Dock, Walkable Short Description🏡 Community amenities: heated pool, boat dock, BBQ📍Walk to shops, grocery store, parks, restaurants🛏️ All bedrooms feature ensuite bathroom 🐶 Dog friendly 🤝 24/7 Guest supportIsla Kiwi (Villa #2) is part of Little Basin Villas upscale community of nine luxury vacation villas, located in the heart of the Art District of Islamorada. Boasting a bayside boat dock and private community pool, our villa offers the perfect blend of relaxation and adventure. Enjoy breathtaking sunsets, waterfront views and island décor & foliage. It uniquely offers three bedrooms complete with their own ensuite bathroom, plus a half bath. It is fully furnished, and offers a private deck, and a top balcony with partial water view. This home is fully stocked with everything you need, and a full time Guest Experience Team to assist in making the most of your stay. The Space🛋️ Living Room: Open-concept living area that features ample

$325

/ night

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Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,

Islamorada, Florida

Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,

🛏 2 bed · 👥 4 guests

Located in Islamorada, Florida, United States. Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis, “Ocean Breeze” – This Beautiful Condominium Features an Ocean view, Protected Boat Slip, Tennis, Gym, and much, much more. This 2 Bedroom condo at Bay Harbour sleeps 4 adults & two children 6 and under. Easy access to the Gulf or Ocean makes this the perfect home port for any fishing vacation. Bring your own boat or rent from any of the many boat rental companies in the area. If your vacation is more about relaxation, then kick back at one of the near-by beautiful sandy beaches. Nested within the gated community of Bay Harbour luxury condominiums, this unit will provide the ultimate base camp for the family to wind down after a day of fishing. Two large bedrooms with private bathrooms plus a sleeper-sofa with half bath can accommodate a family of six or two couples very comfortably. The living room has brand new island style furniture and a 65” LCD TV for those movie nights or football watching days! The che

$240

/ night

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Malayan Palm North 2 Bedrooms, 1 Bath, Garden View

Islamorada, Florida

Malayan Palm North 2 Bedrooms, 1 Bath, Garden View

🛏 2 bed · 👥 6 guests

Located in Islamorada, Florida, United States. Malayan Palm North 2 Bedrooms, 1 Bath, Garden View Poolside,2 Queen Beds,1 Pull OutResort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.Guests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.The Malayan Palm has the option of opening a locked interior door, combining the space into a 3 bedroom, 2 bath home.

$366

/ night

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Beautiful Waterfront Port Antigua Home, Pool, Private Beach

Islamorada, Florida

Beautiful Waterfront Port Antigua Home, Pool, Private Beach

🛏 3 bed · 👥 6 guests

Located in Islamorada, Florida, United States. Beautiful Waterfront Port Antigua Home, Pool, Private Beach Stunning two-story, 3-bedroom resort-style, professionally decorated home. Inside, you'll find a modern and welcoming home with tiled floors, comfortable furniture, and lots of attractive décor and personal touches. The beautiful, modern kitchen has stainless steel appliances. The center island is great to prepare wonderful meals. The incredible kitchen is fully equipped and has a fabulous view out the window. Enjoy your meals at the dining room table with seating for six with gorgeous water views. The three large bedrooms are all furnished with king size beds. The main suite has a large walk-in shower and a separate jetted tub. Want to sleep in late? The main suite has black-out curtains! Relax and enjoy the canal view while sipping your morning coffee or tea from the main bedroom’s screened-in balcony. Walk out to your tropical paradise. The home is professionally landscaped providing privacy for your enjoyment while relaxin

$366

/ night

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The Bonefish House at Tarpon Point

Islamorada, Florida

The Bonefish House at Tarpon Point

🛏 4 bed · 👥 8 guests

Located in Islamorada, Florida, United States. The Bonefish House at Tarpon Point Introducing the "Bonefish House," at Tarpon Point!This opulent, luxury, home is equipped to accommodate eight adults with 4 bedrooms & 4 full bathrooms. The open living space offers easy entertaining and direct panoramic views of the community pool and Atlantic Ocean. The well-appointed and fully equipped chef’s kitchen offers the finest high-end appliances to satisfy everyone’s culinary needs. Whether you are cooking for two or eight, there is plenty of room for everyone to have a seat at the table. Or, eat al fresco right off the main level balcony and enjoy the balmy ocean breeze. The integrated Sonos system offers the ultimate wireless home sound system that streams off the house WiFi network and fills the home with brilliant sound.  This sought after gated community boasts beautifully landscaped grounds, oceanfront pool with heater and chiller, 420 feet of ocean frontage, an observation dock you can fish from, and a beach area where you can launc

$660

/ night

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🌊MOTHER OCEAN🌊 Islamorada Condo w/ Dockage & Ocean Views!

Islamorada, Florida

🌊MOTHER OCEAN🌊 Islamorada Condo w/ Dockage & Ocean Views!

🛏 3 bed · 👥 6 guests

Located in Islamorada, Florida, United States. 🌊MOTHER OCEAN🌊 Islamorada Condo w/ Dockage & Ocean Views! Welcome to Mother Ocean! This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfect for a family or group of friends. It features modern amenities and coastal decor throughout, providing a comfortable and inviting atmosphere for your stay. The spacious living room offers captivating views of the ocean, and opens up to a large screened-in balcony where you can enjoy watching the morning sunrise or spot manatees in the afternoon. The fully equipped kitchen comes with a few extra features such as a coffee bar, air fryer oven and bar seating. The master bedroom has a king-sized bed and its own private bathroom that boasts a walk-in shower, jetted tub, double vanity sinks and a water closet. The second and third bedrooms offer queen and twin sized beds and share a full bathroom. Other amenities include a washer and dryer, central air conditioning, cable TV, and high-speed internet throughout. The c

$267

/ night

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Coastal Elegance Near Theater of the Sea! 2 Stylish Villas, Kitchen, Bayfront!

Islamorada, Florida

Coastal Elegance Near Theater of the Sea! 2 Stylish Villas, Kitchen, Bayfront!

🛏 4 bed · 👥 10 guests

Located in Islamorada, Florida, United States. Coastal Elegance Near Theater of the Sea! 2 Stylish Villas, Kitchen, Bayfront! Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and bustle. Step outside your door and be greeted by the breathtaking beauty of our private beach. Feel the soft sand between your toes as you stroll along the shoreline or soak up the sun on a beach lounger. For those seeking adventure, indulge in various water sports activities nearby, such as kayaking or paddle boarding, Our newly renovated resort boasts an array of amenities to enhance your experience. Take a dip in our sparkling outdoor pool, surrounded by lush tropical gardens. Our friendly staff is always ready to provide recommendations and assist you in planning memorable excursions. Experience the epitome of coastal elegance and create timeless memories at our exclusive retreat. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typ

$731

/ night

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The Snook House ~ 4 Bed / 4 Bath Luxury Oceanfront Home in Islamorada!

Islamorada, Florida

The Snook House ~ 4 Bed / 4 Bath Luxury Oceanfront Home in Islamorada!

🛏 4 bed · 👥 8 guests

Located in Islamorada, Florida, United States. The Snook House ~ 4 Bed / 4 Bath Luxury Oceanfront Home in Islamorada! This impressive home is tastefully decorated and features an open floor plan, soaring ceilings, an unimpeded, nearly 180 degrees of breathtaking ocean vistas and four oversized bedrooms, each with their own bathroom. On the main level, you will find the fully appointed chef’s kitchen which includes the finest high-end appliances to satisfy everyone’s culinary needs, a full size washer and dryer, dining area, and spacious living area that’s leads out to the oceanfront balcony with additional seating for morning coffee, happy hour or dinner al fresco. Don't forget about the covered patio downstairs that is only feet away from the ocean and includes a Weber gas grill and a teak dining table for eight. This is the perfect location to escape from the potent Florida sun, while still being able to enjoy the glistening ocean and balmy breeze.The spacious master bedroom is equipped with a king sized bed and private balcony

$650

/ night

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Island Time:  1BR with Den and Two Balconies

Islamorada, Florida

Island Time: 1BR with Den and Two Balconies

🛏 1 bed · 👥 6 guests

Located in Islamorada, Florida, United States. Island Time: 1BR with Den and Two Balconies Indulge in the spacious layout featuring a well-appointed kitchen complete with a full-sized fridge, stove, coffee maker, toaster, and all the necessary dishes and silverware. Unwind in the welcoming living room, furnished with a sofa bed and dining table, while the balcony beckons with invigorating tropical breezes. A convenient bathroom rounds out the main living space.The bedroom provides a tranquil sanctuary with a luxurious queen bed and access to a den furnished with a full-sized sleeper sofa, perfect for extra guests or a cozy reading nook. The bedroom also boasts an ensuite bath, and the den opens onto a second balcony. Please note that while our property enjoys an oceanfront setting, not all units offer direct views of the ocean.Explore the wealth of amenities at Caloosa Cove Resort and Marina, including a heated pool, beach access, the Safari Lounge, a General Store, and complimentary Wi-Fi. Dive into aquatic adventures with Charte

$216

/ night

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Isla Mirabelle: Waterfront Boutique Resort, Htd Pool, Dock, Walkable

Islamorada, Florida

Isla Mirabelle: Waterfront Boutique Resort, Htd Pool, Dock, Walkable

🛏 3 bed · 👥 6 guests

Located in Islamorada, Florida, United States. Isla Mirabelle: Waterfront Boutique Resort, Htd Pool, Dock, Walkable Short Description🏡 Community amenities: heated pool, boat dock, BBQ📍Walk to shops, grocery store, parks, restaurants🛏️ All bedrooms feature ensuite bathroom 🤝 24/7 Guest supportIsla Mirabelle (Villa #7) is part of Little Basin Villas upscale community of nine luxury vacation villas, located in the heart of the Art District of Islamorada. Boasting a bayside boat dock and private community pool, our villa offers the perfect blend of relaxation and adventure. Enjoy breathtaking sunsets, waterfront views and island décor & foliage. It uniquely offers three bedrooms complete with their own ensuite bathroom, plus a half bath. It is fully furnished, and offers a private deck, and a top balcony. This home is fully stocked with everything you need, and a full time Guest Experience Team to assist in making the most of your stay. The Space🛋️ Living Room: Open-concept living area that features ample seating w/ sectional sofas, m

$321

/ night

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This oceanfront condo is absolutely beautiful.

Islamorada, Florida

This oceanfront condo is absolutely beautiful.

🛏 2 bed · 👥 5 guests

Located in Islamorada, Florida, United States. This oceanfront condo is absolutely beautiful. PROPERTY NAME: The Palms #31379901 Overseas Highway, Islamorada, FLLOCATION: Bayside Condominium MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 79.9DETAILS: Spectacular oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Alligator Reef Lighthouse is easily visible from your master suite or the balcony and you'll be able to watch cruise ships as they pass by the reef and adventure seekers as they paddle their paddle boards or kayaks directly in the waters in front of your unit. This comfortably furnished condo offers flat screen TV in the living area. The Palms is conveniently located near fishing charter opportunities, Bud 'n Mary's Marina and Dive Shop, world-class dining, the Islamorada Art District, tourist attractions and shopping. The condo complex features a pool, hot tub, men's and women's exercise rooms, community

$126

/ night

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Yolo " You only live once" - Fishing Paradise in Islamorada with a 70ft Dock!!!!

Islamorada, Florida

Yolo " You only live once" - Fishing Paradise in Islamorada with a 70ft Dock!!!!

🛏 2 bed · 👥 6 guests

Located in Islamorada, Florida, United States. Yolo " You only live once" - Fishing Paradise in Islamorada with a 70ft Dock!!!! 1440 sf - 2 BedroomsSleeps 4 adults (also includes xtra bed in guest room plus EZ-Bed electric queen Bed and large sectional couch with chaise lounge and cuddler for larger families).Fully renovated and updated in 2021.70ft foot dock and cleaning table.Great ambience, quiet home like feel.Private community beach with beautiful sunsets.Located at White Marlin BeachIslamorada MM74SPORT FISHING CAPITAL OF THE WORLD. Just minutes from Channel 2 bridge known for excellent tarpon, snapper, and other great inshore fishing: as well as the Channel 5 bridge with open access to blue water for awesome offshore fun like Sailfish, Marlin, Mahi, Mutton, Yellow tail and deep drop fishing at your fingertips. If Bone fishing and other flats fishing is what your after, you won’t be disappointed with Florida Bay at your doorstep. This home is smack in the middle of it all.SNORKELING is a no brainer in the Islamorada crystal-c

$233

/ night

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Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views!

Islamorada, Florida

Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views!

🛏 3 bed · 👥 6 guests

Located in Islamorada, Florida, United States. Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views! Short Description🏡 Community amenities: heated pool, boat dock, BBQ📍Walk to shops, grocery store, parks, restaurants🛏️ All bedrooms feature ensuite bathroom 🤝 24/7 Guest supportBayberry Key (Villa #9) is part of Little Basin Villas upscale community of nine luxury vacation villas, located in the heart of the Art District of Islamorada. This is the only Villa that offers an unobstructed water view from the private outdoor terrace and balcony! Boasting a bayside boat dock and private community pool, our villa offers the perfect blend of relaxation and adventure. Enjoy breathtaking sunsets, waterfront views and island décor & foliage. It uniquely offers three bedrooms complete with their own ensuite bathroom, plus a half bath. It is completely furnished and stocked with the essentials needed for an amazing and comfortable vacation. You also have access to our concierge, Guest Experience Team to assist in making the

$380

/ night

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Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool

Islamorada, Florida

Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool

🛏 3 bed · 👥 12 guests

Located in Islamorada, Florida, United States. Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical resid

$1,395

/ night

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Voted best boutique resort in Islamorada! Beach, dockage, pool + more!

Islamorada, Florida

Voted best boutique resort in Islamorada! Beach, dockage, pool + more!

🛏 8 bed · 👥 22 guests

Located in Islamorada, Florida, United States. Voted best boutique resort in Islamorada! Beach, dockage, pool + more! Located in the heart of Islamorada, Mermaid’s Bay Boutique Estate is a secluded oasis situated directly on the bay. Secured by a gated entrance, the property sprawls over 3.5 meticulously maintained acres, with over 300 feet of bay frontage, protected dockage, and a resort-style pool and hot tub.Nestled within one captivating property, our collection of vacation rentals at Mermaid's Bay includes three individual homes, each with their own allure and privacy. The homes may be rented individually or collectively and are available for weekly or longer rentals. (Note: This listing is for booking the entire property. Each unit has its own listing for individual bookings.)The primary home (4 bedrooms, 6 bathrooms) on the property is spacious and perfectly suited for larger families or groups of friends. Two cottages (each with 2 bedrooms and 1 bathroom) are also located on the property, and provide a great option for smal

$2,088

/ night

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Luxury Oceanfront Estate in Islamorada - Your Tropical Paradise Awaits!

Islamorada, Florida

Luxury Oceanfront Estate in Islamorada - Your Tropical Paradise Awaits!

🛏 4 bed · 👥 8 guests

Located in Islamorada, Florida, United States. Luxury Oceanfront Estate in Islamorada - Your Tropical Paradise Awaits! Welcome to Orchid Beach, your ultimate oceanside escape! Nestled directly on the beach, this gated estate greets you with vibrant orchids woven into tropical landscaping, leading to an impressive waterfront home. Offering a unique getaway, the estate provides the perfect blend of togetherness and privacy with living accommodations spread across three distinct pods.The main living pod serves as the estate's heart, featuring a spacious, beautifully appointed living area, a fully equipped gourmet kitchen, a dining space, and an office loft. Large windows and French doors offer stunning ocean views and seamless indoor-outdoor living. The master suite pod is a secluded haven with a king-sized bed, en-suite bathroom, and private terrace. Wake up to a sunrise view over the ocean without leaving your bed. For groups of friends or families, the guest pod includes three guest rooms, each with its own entrance and en-suite ba

$961

/ night

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Beautiful unit in one of the most prestigious Condo Complex in Islamorada

Islamorada, Florida

Beautiful unit in one of the most prestigious Condo Complex in Islamorada

🛏 2 bed · 👥 4 guests

Located in Islamorada, Florida, United States. Beautiful unit in one of the most prestigious Condo Complex in Islamorada PROPERTY NAME: Beacon Reef #30183201 Old Highway, Islamorada, FloridaLOCATION: Ocean side CondoMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 83.2DETAILS: Fully renovated condo that offers inspiring tropical views including the ocean from the open-air balcony accessed from the main living area and the master bedroom suite. This charming, clean, spacious 2 bedroom 2 bath condo has all the comforts for a wonderful vacation. Furnishings have been updated and new items are being added frequently. This unit is located in one of the most desirable complexes in Islamorada. Its central location provides convenient access to everything Islamorada has to offer - world class diving, fishing, and restaurants. If you are feeling adventuresome, snorkel or scuba dive in the crystal clear sea or take a fishing charter to some of the best fishing spots in the world. If you

$109

/ night

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Sun, Sand, and Relaxation Awaits! Ocean View Accommodation w/ Private Patio!

Islamorada, Florida

Sun, Sand, and Relaxation Awaits! Ocean View Accommodation w/ Private Patio!

🛏 1 bed · 👥 4 guests

Located in Islamorada, Florida, United States. Sun, Sand, and Relaxation Awaits! Ocean View Accommodation w/ Private Patio! Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical reside

$533

/ night

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Canary Island Palm North Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out

Islamorada, Florida

Canary Island Palm North Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out

🛏 2 bed · 👥 8 guests

Located in Islamorada, Florida, United States. Canary Island Palm North Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out Poolside,1 King Bed, 2 QueenBeds, 1 Pull OutResort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.Guests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

$405

/ night

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Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin!

Islamorada, Florida

Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin!

🛏 2 bed · 👥 3 guests

Located in Islamorada, Florida, United States. Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin! Oceanfront property offering a unique experience for your tropical escape with views of both Islamorada Sandbar and Alligator Lighthouse! This rental can be separated into two distinct units, each equipped with its own full kitchen, bedroom, and bathroom. Embrace the laid-back atmosphere as you lounge at this property's shared pool with your favorite book or sip on a cool drink.For those with a passion for boating, you'll love the private boat basin right on the property with space to accommodate a boat up to 24 feet. You can easily explore the crystal-clear waters of the surrounding area or embark on a fishing adventure or explore the famous Islamorada Sandbar. Whether you're grilling up fresh seafood on the outdoor barbecue grill, enjoying a family movie night in the living room, or savoring a meal together at the dining table, every moment spent here is sure to create lasting memories.

$209

/ night

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Remodeled Stilt home with Ocean Views

Islamorada, Florida

Remodeled Stilt home with Ocean Views

🛏 3 bed · 👥 6 guests

Located in Islamorada, Florida, United States. Remodeled Stilt home with Ocean Views PROPERTY NAME: Blue Water Retreat137 Ocean Lane, Islamorada, FloridaLOCATION: Oceanside Canal home located in Lower Matecumbe, IslamoradaMINIMUM: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 76.3DETAILS: This home has it all - ocean side Lower Matecumbe location, remodeled in 2009 and 2022. Relax by the splash pool or sunbathe on the roof top and enjoy the spectacular views. There are blue water ocean views from almost every room in this home. This home is located on a canal front lot, offers dockage for a boat up to 30' with easy access to the ocean - a straight shot of about 200 yards to open water from the dock. The wrap-around screened balcony provides a respite after a day on the water. Take a dip in the pool and enjoy some afternoon refreshment. Grill your day's catch on the gas grill and dine at home or take it to one of our many fine local restaurants and let the chef cook it to your specificati

$327

/ night

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Pensacola Beach front Condo

Gulf Breeze, Florida

$141/night

Entire condo in the heart of Pensacola Beach across from the Gulf

Pensacola Beach, Florida

$381/night

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

Islamorada, Florida

$914/night

Isla Kiwi: Waterfront Boutique Resort, Htd Pool, Dock, Walkable

Islamorada, Florida

$325/night

Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,

Islamorada, Florida

$240/night

Malayan Palm North 2 Bedrooms, 1 Bath, Garden View

Islamorada, Florida

$366/night

Beautiful Waterfront Port Antigua Home, Pool, Private Beach

Islamorada, Florida

$366/night

The Bonefish House at Tarpon Point

Islamorada, Florida

$660/night

🌊MOTHER OCEAN🌊 Islamorada Condo w/ Dockage & Ocean Views!

Islamorada, Florida

$267/night

Coastal Elegance Near Theater of the Sea! 2 Stylish Villas, Kitchen, Bayfront!

Islamorada, Florida

$731/night

The Snook House ~ 4 Bed / 4 Bath Luxury Oceanfront Home in Islamorada!

Islamorada, Florida

$650/night

Island Time: 1BR with Den and Two Balconies

Islamorada, Florida

$216/night

Isla Mirabelle: Waterfront Boutique Resort, Htd Pool, Dock, Walkable

Islamorada, Florida

$321/night

This oceanfront condo is absolutely beautiful.

Islamorada, Florida

$126/night

Yolo " You only live once" - Fishing Paradise in Islamorada with a 70ft Dock!!!!

Islamorada, Florida

$233/night

Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views!

Islamorada, Florida

$380/night

Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool

Islamorada, Florida

$1,395/night

Voted best boutique resort in Islamorada! Beach, dockage, pool + more!

Islamorada, Florida

$2,088/night

Luxury Oceanfront Estate in Islamorada - Your Tropical Paradise Awaits!

Islamorada, Florida

$961/night

Beautiful unit in one of the most prestigious Condo Complex in Islamorada

Islamorada, Florida

$109/night

Sun, Sand, and Relaxation Awaits! Ocean View Accommodation w/ Private Patio!

Islamorada, Florida

$533/night

Canary Island Palm North Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out

Islamorada, Florida

$405/night

Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin!

Islamorada, Florida

$209/night

Remodeled Stilt home with Ocean Views

Islamorada, Florida

$327/night