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Located in Islamorada, Florida, United States. Beautifully Renovated 2 Bedroom Oceanfront Home 132 Atlantic Lane - Looking for your next home away from home You cannot go wrong with this recently renovated two-bedroom two bath canal home in Lower Matecumbe at the 76-mile marker. This home has everything you need for your next get-away in Islamorada. Only one property away from the Atlantic Ocean, you can literally watch the sun rise from the dining room table. Give us a call to book your next Islamorada Vacation. You will not be disappointed. If booking more than a year in advance current prices may not reflect the annual cost of living increase. Many of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. Please note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a

Located in Islamorada, Florida, United States. Family Getaway! 3 Tropical View Units, Outdoor Pools, Pet-friendly! 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 residential or

Located in Islamorada, Florida, United States. Blue Ocean Estate, 3 bedroom ocean front in Islamorada, rented by Island Villa Mile Marker 81 - OceanfrontWelcome to your exclusive oceanfront oasis in Islamorada, in the Florida Keys! This 3-bedroom, 3-bath rental estate is a haven of luxury, featuring panoramic views of the Atlantic including Alligator Light, a private pool, and access to over 250' of open beach front!Inside, a stylish living area with coastal decor welcomes you, complemented by a fully equipped kitchen. Each bedroom offers comfort and charm, with the master suite providing a king bed and large en-suite bath.  The first guest bedroom features 2 queen beds, and the second features a queen and a full bed with a trundle bed underneath.  Outside, the private pool and sun deck invite relaxation, while the beach is just steps away. Explore the nearby attractions, indulge in water sports, or simply savor the breathtaking sunrises and sunsets. Watch the kids run, swim and play on one of the few beaches in Islamorada.Escape t

Located in Islamorada, Florida, United States. Caribbean style home Islamorada - Oceanfront resort privileges. Indulge in the allure of the Florida Keys with our Caribbean retreat nestled in the heart of Islamorada. Immerse yourself in a 2-bedroom, 2-private bath with Queen beds comfortably accommodating up to 4 guests.Experience the vibrant ambiance of our home through its beautiful Caribbean décor, open ceilings, and exquisite detailing, featuring solid wood doors, stone flooring, and an expansive living and dining area. Elevate your culinary adventures in the amazing chef-appointed kitchen equipped with Wolf appliances and a Subzero refrigerator.Located just across the street from The Caribbean Resort, revel in the luxury of full resort privileges, including access to a beach-entry pool and fishing pier. Dive into the tropical lifestyle with complimentary use of bicycles, kayaks, paddle boards, and fishing rods. Whether you’re indoors or outdoors, the authentic Caribbean atmosphere surrounds you.Your comfort is our priority, wi

Located in Islamorada, Florida, United States. Islamorada Oceanfront Estate, Pool, Beach Cottages-- Sea Ranch -- Florida Keys Island Villa Rental Properties offers this two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marker 83.This stunning property is truly a tropical paradise with a private, sandy beach and observing pier.Relax at the beach or cool down in the beachside pool. The front home sits waterfront with two bedrooms and two bathrooms.The garden cottage sits back on the property with two bedrooms and one bathroom. Entertain in the pool room with pool table, wet bar, poker table and more.The ocean front paradise is also a 'Destination/Wedding Location!'Dockage Note: Dockage consists of a skiff dock for shallow boat docking only. Perfect for back country skiff with shallow draft, kayaking, fishing, or  chilling out!Oceanfront Beach CottagesThere is an additional fee for approved pets. Please inquire.**View more of our exclusive properties here in Islamorada Florida Key

Located in Islamorada, Florida, United States. 10 Bedroom Private Ocean Front Estate The Island Palm Estates is a newly constructed estate that includes 2 separate, luxurious homes with all the modern conveniences and casual charm that a premiere island getaway should have. The homes lay out on a large secluded ocean front beach with dense palm fauna surrounding 2 amazing pools and a gym shared by both houses that includes, Weight Bench, Free Weights, Elliptical Machine and Treadmills. Each home has private parking, its own pool, and expansive oceanfront porches for entertaining, relaxing and grilling. Each house can be rented individually for a private getaway or together for a large group. Please note, we don't allow weddings on the property.. There is plenty of space for everyone to spread out and enjoy themselves on this almost 2 acre property. In addition to the two pools you will also enjoy 200' of private beach and viewing dock. Key Features of Island Palm Estate:South House:-3 Bedroom / 2 Bathroom – The first bedroom featur

Located in Islamorada, Florida, United States. Oceanfront Paradise Retreat! Outdoor Pool, Pets Allowed, Near Coral Bay Marina 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 resi

Located in Islamorada, Florida, United States. Open Ocean Views - 2 separate properties -House & Cottage With Dockage & Pool 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)The recently renovated Oceanside House & Cottage is located directly on the ocean with amazing morning sunrises over the ocean. The full moon rise over the water in front of the house is breathtaking! 3 Bedroom - 2 bath House:Gorgeous new kitchen in fully renovated house with 180 degree ocean views. Glass enclosure bathrooms and amazing open balcony as well as screened in balcony overlooking pool and ocean. Stunning!2 Bedroom - 2 bath Cottage: The modern cottage has a beautiful cook's kitchen equipped with brand new appliances. Each bathroom is entirely new with modern fixtures including glass showers. There are 2 bedrooms, each with a private full bathroom. The brand ne

Located in Islamorada, Florida, United States. Island Beach House Oasis Your Memory Maker awaits There is luxury, luxury and unrivaled, and then there is the Bay front Island Beach House Oasis that offers that and more. Situated on just a hair under one acres of manicured Islamorada shore front, this unique property reveals the very best in tropical vacations. The property only recently became available. Sleeping 16, the six bedroom, five bathroom retreat will conjure reveries of leisure taken to new heights.

Located in Islamorada, Florida, United States. Waterfront... The Sapodilla House... Islamorada Family Estate Home... The Sapodilla House - The Sapodilla House is one of Islamorada’s gems. This tropical, sprawling estate has every amenity and then some. Enjoy island living at its finest from the moment you drive through the private gates.The spacious main house is beautifully furnished and equipped with everything you will need. Cook island inspired meals in the high-end kitchen and choose to dine in the formal dining area, breakfast nook with garden views or outside under the tiki hut. The main house features three king ensuites, and a kids' room with full-size bunk beds and your own personal mini arcade. Enjoy the company of family and friends in one of the conversation areas or over a game of pool. The detached pool house includes an additional king bedroom and bathroom. Step outdoors and the lush, tropical landscaping will have you feeling like you’re at your own private resort. Outdoor entertainment areas include an expansive o

Located in Islamorada, Florida, United States. Beautiful unit in one of the most prestigious Condo Complex in Islamorada PROPERTY NAME: Beacon Reef #40683201 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: excellent choice for your vacation getaway, whether you're planning on staying a month or the entire season, this is a great unit. Beacon Reef is centrally located in the Heart of Islamorada making it convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. This charming, clean and bright 2 bedroom, 2 bath condo has all the comforts for a wonderful vacation. Enjoy gentle ocean breezes from your private balcony while overlooking the pool, beach, docks, and manicured tropical grounds. If you are feeling active, snorkel in the crystal clear ocean or take a fishing charter to some of the best fishing spots in the world. If you bring your own boat, docka

Located in Islamorada, Florida, United States. Cozy Coastal Haven for Relaxation! With Pools and Water Sports Onsite! 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 residential

Located in Islamorada, Florida, United States. Wake up in Paradise! Florida Keys - Islamorada - 6-month minimum rental (6 month minimum rental) - $5,400 per month (boat slip not included).Conveniently located on a quiet street in Port Antigua, this fully renovated 3-story townhouse offers comfort and ease. The unique three-story layout features a large entertainment living area with a half-bath, pool table, bar, and living area, along with two terraces on the first floor. The second floor boasts a spacious bedroom, full bath, updated kitchen, living area, and a large balcony with a stunning view of the cove and ocean. A spiral staircase leads to the third floor, where the large master bedroom with a walk-in closet, full bath, and large terrace await. Newly installed impact windows and doors ensure your comfort and safety.Enjoy your coffee with a unique and spectacular ocean view each morning. Are you looking to get away from the harsh winter? It's a little sanctuary where you can relax, decompress, and immerse yourself in the true

Located in Islamorada, Florida, United States. Cozy Cottage in the Heart of Islamorada Little Bay Cottage - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a total of 18 people. The Upper & Lower Duplex are each 1,500 sq ft units, each with two bedrooms, two full baths, full modern kitchen, laundry, family room, and 10' x 40' porch overlooking the bay. Each unit accommodates 6 people (upper master bedroom: king and twin murphy, guest bedroom: two twins, sofa sleeper) (lower master bedroom: queen and twin murphy, guest bedroom: two twins, sofa sleeper) The Cottage is a bright and airy 1,250 sq ft unit with a huge master bedroom (king & sofa bed), 2nd sunroom with sofa bed and twin murphy bed, two full baths, laundry room, and combined family room, kitchen, & great room. The Cottage accommodates 6 people. All units come equipped with ce

Located in Islamorada, Florida, United States. Make Your Trip More Enjoyable! Free Parking, Pets Allowed, Onsite Pool Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive into water sports. Enjoy nearby attractions like Anne's Beach, Theater of the Sea, and the History of Diving Museum.Experience a slice of paradise in this authentic room at our boutique beachfront resort! We offer a private lounge on the beach where you can relish the authentic island life experience. Enjoy a bike tour through the island, an outdoor pool, and a sun terrace with breathtaking views of Alligator Reef Lighthouse. Embark on boating excursions and dine at our delightful American restaurant. Relax, rejuvenate, and explore the serene beauty that awaits.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of $100/night/unit on the credit/debit card provi

Located in Islamorada, Florida, United States. 2nd Floor Duplex on Gated Bayfront Property PROPERTY NAME: Little Bay Upper Duplex82246 Overseas Highway, Islamorada, FloridaLOCATION: Upper Duplex located directly on the Florida BayMINIMUM STAY: Weekly or MonthlyMILE MARKER: 82.2DETAILS: - Located on a one-acre lush tropical setting in a gated compound directly on Florida Bay- One of 3 separate units for rent by the week or month, each sleeping up to 6 people- Protected dockage for up to a 34-foot boat- Sunning area with lounge chairs on the peninsula- Hammocks, pergola, and tiki for relaxing- Panoramic views of Florida Bay from the covered balcony- Spacious interior with 2 bedrooms, 2 bathrooms, and a queen-size sleeper sofa- Updated kitchen with new appliances and granite countertopsThis vacation rental is the perfect place to relax and enjoy the beauty of Florida Keys. With its protected dockage, you can safely moor your boat and enjoy all the water activities the area has to offer. Or simply relax on the sunning area or in one o

Located in Islamorada, Florida, United States. You Don’t Want to Miss This! Beachfront, Onsite Pool, Near Coral Bay Marina 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. Princess Palm North 2 Bedrooms, 2 Baths Poolside Poolside, 1 King Bed, 2 Queen Beds, 1 PulloutResort 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.

Located in Islamorada, Florida, United States. A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool ''BEAUTIFUL BAY-FRONT PROPERTY!!!!'' NEW POOL Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 10. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath.Entire house has been remodeled, fully furnished, with a 90 ft Dock. Bring your clothes, boat, fishing and dive gear. Located in desirable "Islamorada" where you will have easy access to some of the best back-country fishing, and or ocean fishing which would include all of the paddle boarding, snorkeling, and diving that anyone would ever want, just minutes from Channel 5 and channel 2. Dog beach is 3 min away by boat. You will love the back porch outdoor living space which includes your own Bar over looking the water. This is a Boating, Fishing Scuba Diving/Snorkeling Paradise.House, 3 Bedrooms, 2 Baths, Sleeps 10213 Tollgate Blvd., Islamorada, Florida Keys mile marker 73 bay sid

Located in Islamorada, Florida, United States. A Place You'll Surely Enjoy! Courtyard View, Free Parking, Onsite Pool Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive into water sports. Enjoy nearby attractions like Anne's Beach, Theater of the Sea, and the History of Diving Museum.Experience a slice of paradise in this authentic room at our boutique beachfront resort! We offer a private lounge on the beach where you can relish the authentic island life experience. Enjoy a bike tour through the island, an outdoor pool, and a sun terrace with breathtaking views of Alligator Reef Lighthouse. Embark on boating excursions and dine at our delightful American restaurant. Relax, rejuvenate, and explore the serene beauty that awaits.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of $100/night/unit on the credit/debit card provi

Located in Islamorada, Florida, United States. Port Antigua Waterfront Home With Private Beach Access This Keys Home is Located in Beautiful Port Antigua. 4 Br/ 3 Ba Sleeps 8 Comfortably. All Rooms Have Queen Sized Beds. Large Kitchen and Dining Room. Large Gathering Areas Throughout the House. There is Also a Barbecue and Gas Stove Downstairs. Features 60' Dock for Your Boat With Deep Water Access to the Florida Gulf and Atlantic Ocean in Minutes. Enjoy Fishing in the "fishing Capital of the World". Private Beach Access With Tiki Huts and Barbecues for Your Use. Golf Cart and Multiple Bicycles Available.

Located in Islamorada, Florida, United States. High Tides and Good Vibes! 4 Spacious Units, Outdoor Pool, Free Parking 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 residential

Located in Islamorada, Florida, United States. Romantic Oceanview Retreat with Beach Access at The Islands of Islamorada Resort Experience Coastal Luxury at The Islands of Islamorada ResortWelcome to Your Perfect Oceanview Suite!Immerse yourself in coastal elegance and tropical splendor at The Islands of Islamorada. Our luxurious one-bedroom oceanview suites are designed for discerning travelers seeking both relaxation and adventure.Suite Highlights:- King Bed: Unwind in a plush king-size bed with spectacular ocean views.- Spacious Living Area: Relax and entertain in style with ample living space.- Outdoor Lounge Area: Soak in breathtaking ocean vistas and serene sunsets from your private outdoor space.- Convenient Amenities: Enjoy dedicated outdoor parking, a mini fridge, microwave, and coffee station for added convenience.- Daily Housekeeping ServiceResort Features:- Beach Access: Step directly onto soft sandy shores for sun and sea.- 24-Hour Fitness Pavilion: Keep up with your workout routine anytime.- Outdoor Fitness Classes: J

Located in Islamorada, Florida, United States. High Tides and Good Vibes! 2 Relaxing Units, Pet-friendly Property, Pool Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive into water sports. Enjoy nearby attractions like Anne's Beach, Theater of the Sea, and the History of Diving Museum.Experience a slice of paradise in this authentic room at our boutique beachfront resort! We offer a private lounge on the beach where you can relish the authentic island life experience. Enjoy a bike tour through the island, an outdoor pool, and a sun terrace with breathtaking views of Alligator Reef Lighthouse. Embark on boating excursions and dine at our delightful American restaurant. Relax, rejuvenate, and explore the serene beauty that awaits.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- These are TWO separate hotel rooms. Rooms are individually unique and may not be adjoi