72,107 properties available

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

Located in Islamorada, Florida, United States. Indulge in Home Like Comfort! Courtyard View, Free Parking, Pool, Pets Allowed 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 ca

Located in Islamorada, Florida, United States. Your Majestic View in Islamorada! Swimming Pool, Kitchenette, Pets Allowed! Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of the guest rooms and suites in our three-bedroom house is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual elegance of the tropics with our resort amenities. Guests have access to all the amenities they might possibly need right on the premises, including a restaurant, bar, swimming pool, and slips for those visiting with boats. But if you want to venture offsite, we have a shuttle service that can take you around.PLEASE NOTE:- The property requires a damage deposit of USD 100/night/unit on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in is subject to availability upon

Located in Islamorada, Florida, United States. Port Antigua NEW Luxury one bedroom/2 bath apt with pool/spa/steam in Islamorada Be the first guest at a one of a kind, brand new, boutique style accommodations in one of the most beautiful areas of the Florida Keys. Serenity. Luxury. Privacy. Peaceful. All amenities in this lavish first floor apartment abound, for the discerning couple. Honeymooners, couples celebrating an anniversary or wanting a quiet get-away from the hustle and bustle of city life or snow? Welcome! From luxury (Comphy) sheets found only in the finest hotels and spas, to your own private pool, private hot tub, and spa/steam room fully equipped with top of the line towels, body wash, shampoo, and conditioner. Just pack your tooth brush and bathing suit, we'll take care of the rest. The outdoor area has an outdoor summer kitchen with bar b q, refrigerator, outdoor sink, side burner for concocting your own creations, outdoor dining area or bring your dinner indoors; order in or feast at many fine dining establishmen

Located in Islamorada, Florida, United States. Relax and Unwind! Courtyard View, Free Parking, Onsite Pool, Near Anne's Beach 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 ca

Located in Islamorada, Florida, United States. Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property 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 p

Located in Islamorada, Florida, United States. Relax and Recharge in Islamorada! 2 Relaxing Units, Pets Allowed, Outdoor 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 b

Located in Islamorada, Florida, United States. Dive Into Your Dream Vacation! Beachfront, Outdoor Pool, Near Hurricane Monument 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 re

Located in Islamorada, Florida, United States. Relaxation at Its Finest in Islamorada! Free Parking, Swimming 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 provide

Located in Tierra Verde, Florida, United States. Waterviews/Renovated 2024/Free Amenities/Location Discover the perfect retreat at our charming 2-bedroom, 2-bathroom condo, ideally suited for a relaxing vacation for up to 4 guests. Nestled on the 2nd floor of the well-maintained Holiday Island community, this condo offers both comfort and convenience for your next beach escape.Your Coastal Haven Includes:- Fully Equipped Kitchen: Prepare meals effortlessly with a coffee maker, blender, toaster, mixer, and all necessary pots, pans, dishes, and cutlery.- Comfort & Convenience: All linens, towels, bedding, and pillows are provided. Enjoy the ease of a self-condensing washer/dryer combination unit in the condo.- Welcome Basket: Start your stay off right with a welcome basket filled with snacks, discounts, and a starter supply of paper products and necessities.- Parking: One parking pass is provided for your convenience (pass required).- Professional Cleanliness: The condo is professionally cleaned and sanitized for your peace of mind.- E