58,368 properties available

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

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

Located in Islamorada, Florida, United States. Hidden Gem Duplex in Heart of Islamorada! Sleeps 8 Summary:This truly is a Hidden Gem in the heart of Islamorada. Nestled in the trees just a few steps from one of the most amazing sunsets in the upper Keys. Walking distance to all the wonderful shops, restaurants and breweries that Islamorada has to offer. Bikes and Kayaks can be rented steps away from the front door of this unit. Want to find a place that you'll want to return year after year? Look no further!The Space:This rental is two separate units, one upstairs and one downstairs, with separate access to each. There is no interior access between the two units. Great for large groups and families!This unique property was originally built as motel in the 1950's. We have taken it upon ourselves to give it a facelift! New split AC units in every room! Cool down when you get inside from that Florida heat! BrrrrrThe upstairs is a 2 bedroom/2 bath with a full kitchen. Both bedrooms have King beds.The downstairs is a 2 bedroom/2 bath w

Located in Islamorada, Florida, United States. Paradise with surrounding beaches and amazing fishing!!! Welcome to paradise! This waterfront home is in the heart of the Florida Keys. This 3 bedroom 3 bath home comfortably sleeps 10 adults. It features a 75 ft dock w/ a community boat ramp, full modern kitchen, spacious living and dinning area upstairs and downstairs. Charmingly furnished, the home also includes a washer/dryer, a/c, wifi, flat screen TV's. Home has plenty of space to park boat trailer and toys.

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

Located in Islamorada, Florida, United States. HUGE DISCOUNTS FOR THE FALL September-December. Book now! Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Persons / **MONTHLY RENTALS ONLY!!) Come and enjoy our Paradise Found 2nd home. FREE BOAT DOCKAGE (with proof of insurance) In the fishing capital of the world, Islamorada. If you have never experienced the Keys in the summer, the weather is VERY mild! Just like the winter is warm, the summer is cool. There is always a breeze the the temps are high 70's to mid80's. See our beautifully furnished 2 BR 2 BA Condo is on the second floor.(First is parking only) Convenient Spiral Staircase from back porch directly down to grounds. Only this floor has the stairs, others have to go through a building stairwell or elevator. The master bedroom and outside patio gives a beautiful view of the OCEAN. Wake up to the sunrise. Inside find a fully equipped kitchen, washer/dryer, games, books, comfortable furniture, and smart TVs throughout. Tile floors for easy care. Go out into the

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

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

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

Located in Islamorada, Florida, United States. 15% to 20% OFF LUXURY HOUSE CLOSE TO THE OCEAN IN PORT ANTIGUA Perfect vacation home for those who want to experience privacy and paradise in the Florida Keys! The house features plenty of parking space, both covered and uncovered, as well as a 75-foot dock, a dock-side chickee hut, and easy deep water access to the Bay and Ocean. Inside, the home has been updated with wood-look ceramic floors, a modern kitchen and bathrooms. The main-floor bedrooms are comfortable for guests and family, while the third-floor primary suite is a true oasis with a walk-in closet, a private deck overlooking the water and mangroves, and a luxurious bathroom. Port Antigua offers a private Homeowners' Beach with tiki huts and grill stations along a white sandy beach. Att: renting golf cars and boat lift separate. Contact host

Located in Islamorada, Florida, United States. Newly renovated Port Antigua canal front home with convenient dockage! Fall Special Rates!! Discounted rates through December, inquire within! Welcome to your dream vacation getaway in the heart of Islamorada! This charming waterfront home on Lisbon Court offers the perfect blend of comfort, convenience, and deep water dockage. Located in a peaceful residential neighborhood, this property provides a relaxing escape while still being close to all the attractions and activities that the Florida Keys have to offer.Key Features:Beautifully Renovated home with all of the comforts you want/need in your vacation home!Waterfront Location: Enjoy direct access to the crystal-clear waters of the Florida Bay, making it ideal for boating, fishing, snorkeling, and other water sports.Private Dock: The property features a private dock where you can moor your boat or simply relax and soak in the picturesque sunsets.Spacious Accommodations: The house offers [number of bedrooms] bedrooms and [number of b

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

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

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

Located in Islamorada, Florida, United States. Bay Islamorada BeachHouse POOL!70' DOCK boat rent Summary:Enjoy the keys life in style living in this beautifully furnished or 2 Bedroom, 1 Bath, canal front retreat with room for boats at the private 70' large concrete dock attached fish cleaning station which is an obvious necessity in the Keys. Easy access to the bay-side or ocean-side. This oasis is within the Islamorada Village limits and offers all the comforts of home. The 2017 Yamaha Jet boat and the 2018 Scarab are available rent or via private charter with CaptainThe Space:Property has a brand new pool!This listing is for 1 side of the duplex. Specifically the side closest to the bay/gulf side. Each side of this luxury duplex has peekaboo views of the ocean and comfortably accommodates with two queen beds and one queen convertible sofa. The kitchen includes a large complete set of cookware, dinnerware and all utensils as well as all appliances designed with the gourmet in mind. All amenities, including a coin washer and dryer

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

Located in Islamorada, Florida, United States. Keys to Relaxation! Pool, Pets Allowed, Short Drive to Florida Keys Airport 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 residen

Located in Islamorada, Florida, United States. Brand New Beach House 1st Floor W Pool Beach &Dock Summary:This listing is for the newly built 2020 downstairs of the duplex. You can Enjoy the keys life in style living on the ground floor of this beautifully furnished 3 Bedroom, 2 Bath, canal front retreat with room for boats at the private 70' large concrete dock with attached fish cleaning station which is an obvious necessity in the Keys.and easy access to the bay-side or ocean-side. The 2018 Scarab Center Console Jet boat is available to rent.The Space:Upstairs is available as an add on or vice versa downstairs is the space you are renting front and back yard is common areasGuest Access:This is the base of the duplex that is now being made available to youThe Neighborhood:Located on a Deep-Water canal, with and outside shower. This is an ideal location for all water-sports, fishing, diving, snorkeling and boating with either a 500' walk to the Atlantic Ocean Beach or use the key to the private gated White Marlin beach with Gulf b

Located in Islamorada, Florida, United States. Beautiful 7 BR estate in Islamorada, FL keys, with pool, dockage, & sandy beach! Island Villa Rental Properties offers fantastic panoramic views of the Atlantic Ocean from this 7 BR, oceanfront home in Islamorada, FL Keys. Located at MM 77 on Lower Matecumbe Key, this gated estate has everything needed for a Keys vacation… Pool, beach, views and sunrises!The grounds have it all— At first glance, the magnificent pool, and pool deck overlooking the Atlantic is what most gravitate too. But if your guests want to get a little bit natural, it’s just steps down to your own private sand beach with palms and shade. Pitch your canoes in here or go snorkeling! Walking through the grounds shows magnificent, well manicured local tree and plant gardens.Private 75’ of dockage is included and is located off the property and around the corner on a canal via your own parcel.The interior of Ishmael’s has a unique set up and features a large master bedroom and bath. Several guest bedrooms are located thr

Located in Islamorada, Florida, United States. Live your best Vacation life in the Florida Keys! Discover the charm of island living, nestled in the heart of Islamorada, Florida. This freshly remodeled rental property boasts two separate units, each with their own exterior entry, offering flexibility and privacy for families. With three spacious bedrooms and three modern bathrooms this home caters comfortably to families, professionals, and anyone looking to soak in the serene atmosphere of the Keys.The upper unit of the home opens to three breezy balconies, ideal for soaking in the sun, or watching the manatees play. The interiors are thoughtfully designed with convenience and style in mind, featuring up-to-date amenities and finishes that are sure to appeal to those with an appreciation for modern coastal living.Parking is plentiful and hassle-free, ensuring that guests always have a place to store their vehicles and boats securely. The property’s location is a standout feature, defining leisurely lifestyle with access to som

Located in Islamorada, Florida, United States. Beautiful 2/2 Islamorada Home Directly on Florida Bay (28 Day Minimum Rental) Our home is in Islamorada, in the middle Florida Keys. To be more specific, we are on Lower Matecumbe Key, which is the southernmost island in Islamorada, at exactly Mile Marker 74, on the bayside. Our home is a 2/2, and can comfortably sleep four, with two bedrooms upstairs. The Master has a queen bed, and a private bath. The second bedroom has twin beds, and a separate bath. If more room is needed, or for families with young kids or teenagers, it's possible for at least two to "camp out" on comfortable air mattresses upstairs in the family room. Downstairs there is a laundry room/workshop, and a more "rustic" game room/bar with a refrigerator for water/soft drinks/beer/bait.

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

Located in Islamorada, Florida, United States. Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada Welcome to Infinity Bay Islamorada, an infinite paradise with infinite possibilities in the heart of the Florida Keys. This exclusive property offers a blend of sophistication and tranquility, where guests can unwind in style against the backdrop of crystal-clear turquoise waters and swaying palm trees. Infinity Bay is a tropical paradise that stands out as the pinnacle of luxury accommodations where you won’t know where the pool ends, and the bay begins.This luxurious 9-bedroom, 10-bathroom estate offers the ultimate retreat experience with its stunning bayside location and impressive amenities. With over 7,000 square feet of living space between the main house and the detached guest house, there's plenty of room to spread out and unwind in style. When you walk into the main house, you’ll be in awe of the abundance of natural light pouring in from the floor-to-ceiling window that leads out to the bay. The op

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