72,107 properties available

Located in Islamorada, Florida, United States. Beautiful Maison #307 Maison Matecumbe #307 - Maison Matecumbe is an exclusive gated and private boutique complex comprised of 9 units. Centrally located right in the heart of Islamorada within walking and biking distance to many restaurants, cafes, shopping, marinas and Islamorada's Art District. The unit has been totally renovated, brand new kitchen, beautiful bathrooms, decor and bedding. The unit offers an open lower level living room with kitchen and guest bedroom and full bath. Beautiful views of the Atlantic from the screened balcony. The upper level has a king master en suite and third bedroom with two queen beds. Newly renovated swimming pool and hot tub to spend your days lounging along with Maison's beach, outdoor kitchen, tiki hut and spa. VACATION RENTAL LICENSE: 24-0074If booking more than a year in advance current prices may not reflect annual cost of living increase. Many of our guests’ re-book the same property on an annual basis. No reservation is confirmed until you

Located in Islamorada, Florida, United States. Best Location in Islamorada!! Beach access - Boat trailer parking! Gorgeous and highly appointed luxury Island villa with beach access. You are right in the middle of it all with this perfect location. Walk or bike to some of the best restaurants and shopping Islamorada has to offer.

Located in Islamorada, Florida, United States. Jamaican Palm House 3 Bedrooms, 2 Bath, Poolside Poolside,3 Queen Beds,1 Pull OutWelcome to the Jamaican Palm. Our most recently renovated home is a sight to behold. Every detail and fixture was handpicked and custom crafted from the finest materials and builders.Inspired by the Caribbean lifestyle and design from Ocean Gardens Showroom. The Jamaican Palm is an expansive 3 bedroom, two-bathroom single home with a large great room, chefs kitchen and outdoor wrap-around veranda. Chisel stone flooring, granite countertops, Keys Stone Coral wall and custom cabinets are just a few of the high quality features the home holds. The chefs commercial kitchen features a Wolf stove, Subzero refrigeration and a separate built-in wine cooler.Nautical decor includes one of a kind Marine Antiques and ship lighting throughout the home. Like all our other homes, The Jamaican Palm also comes with a washer-dryer, Weber BBQ gas grill, wireless Internet and cable TV.This home includes a full washer-dryer, W

Located in Islamorada, Florida, United States. Bayside Retreat - Adorable 3 Bedroom Bayfront Duplex with Dockage Bayside Retreat - Completely renovated bayfront duplex home. This bayfront home consists of three bedrooms and three baths in Lower Matecumbe. With charming island decor and the open concept living room, kitchen and dining area, the home is light and airy. The screened balcony directly off the kitchen enables you to enjoy outdoor dining with beautiful bay views. The master en-suite with a king bed and bay views, and the guest room with two twin beds are located on the main level. The loft queen en-suite on the second level with sliding doors leading out to an open balcony offers open Gulf views to the west and ocean views on the east. This home offers both ocean views and bay views from the kitchen and living room. Dockage for smaller boats and skiffs up to 24' with easy bay access and ocean access through Channel 5 Bridge. Enjoy paddle boarding and kayaking right from the bayfront beach area. There are 2 paddle boards f

Located in Islamorada, Florida, United States. Tarpon Bend ocean view with boat lifts 3/2 Waterfront Home in Lower Matecumbe Key in Islamorada, Florida. Featuring a 70' ft private dock with 2 boatlifts (1- 10,000 lbs capacity, 1- 20,000 lb capacity)- both available for rental separately. Home is minutes away from most attractions. This beautiful home accommodates up to eight people and is completely decorated.Master Bedroom has a King-size bed with a flat panel LCD Television. Southern facing window lets in plenty of natural light. Bedroom features a master bath and a walk in closet with ample room for storage.Bathroom #2 has a queen sized bed and a private televisionBathroom #3 has two full size bunk beds and a private television. One full sized bathroom in addition to master bath is conveniently located by bedrooms.The living room has an entertainment center with a flat panel LCD Television. Lovely Kitchen /dining area featuring a table for 8. Upstairs balcony extends width of property and contains a BBQ and seating area. Do

Located in Islamorada, Florida, United States. Perfect Home for a get away! Private homeowners beach, enjoy Islamorada. Perfect home for a get away! Home is located in Islamorada. 3 bedroom 3 bath gorgeous private homeowners beach and private dock, close to the best restaurants, and sight seeing. Peaceful, quiet and relaxing! Just what is needed to take your mind off of business and a great place to spend the winter months in turquoise, warm waters. Fish, read a book, swim, head to Key West, shop, eat, drink, enjoy the Florida Keys.

Located in Islamorada, Florida, United States. Sunset Splendor: 2 Units Near Theater of the Sea! Parking, Pool, BBQ Facilities 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 ty

Located in Islamorada, Florida, United States. Oceanside townhome 2/2 with boat ramp and dockage This beautiful newly renovated townhouse is the prefect vacation home for you and your family. The third floor has a master bedroom with king bed and bathroom with a balcony that has ocean views. The second floor has a bedroom with queen bed and bathroom right off of the living room and fully equipped and updated kitchen with a huge island. There is a sleeper sofa in the living room. The balcony on the second floor provides you with a view of the pool, tennis courts, pickle ball, shuffle board, tiki hut with picnic area, charcoal grill, and dock. You have a view of the dock where you can keep your boat up to 25' as stated in boat registration. The dock has fresh water, electric, 2 filet stations. There is a community boat ramp which you have access to at anytime as long as you have provided insurance and registration to the dock master. On the first floor there is a garage where you can store your fishing rods, a freezer to store your

Located in Islamorada, Florida, United States. Oceanfront Condo @ Maison Matecumbe - 3 bedrooms overlooking pool, Ocean & beach Welcome to your dream vacation home in Islamorada, the jewel of the Florida Keys! This 3-bedroom condo boasts a prime location, with breathtaking views of the crystal-clear pool, Atlantic Ocean, and glistening white sand beach.As soon as you step inside, you'll be enchanted by the bright and airy living space. The living area and balcony features plenty of entertaining areas inside and out… Perfect for relaxing after a long day of fishing and swimming. Add optional dockage to any rental. Contact for rates.The master suite features a king-size bed and a private balcony with stunning views of the pool and beach. The other two bedrooms offer a full-size bed and two twin beds, respectively, making it the perfect accommodation for families or groups of friends.Step outside onto your private balcony and soak up the sun while enjoying the panoramic views of the pool, hot tub, and beach. Sip on a refreshing drink

Located in Islamorada, Florida, United States. Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe Bay Harbour A-304 – Beautiful three bedroom two and a half bath luxury penthouse condo located at mile marker 74.5 bayside. This condo is nicely decorated, fully appointed, and very spacious for you and your family. The unit has a beautiful, screened lanai off the living room and master bedroom with brand new furnishings to relax and watch the sun rise over Alligator Reef. The complex has a pool, hot tub, gas grills, tennis courts, weight room, dockage, fish cleaning stations, and a community club house. The unit has recently been updated to make your stay even more comfortable and enjoyable. It has Wi-Fi as well as cable. The condo includes all linens and is equipped with a full washer and dryer. The condo overlooks its 50-foot private boat slip in a protected harbor with deep water access. There is immediate bay access and quick ocean access via Channel Two and Channel Five bridges. Fish cleaning stations, s

Located in Islamorada, Florida, United States. Mini Ray's of Sunshine Mini Ray's of Sunshine - Beautiful New Pool Home located in a gated community in the Heart of Islamorada. This home, designed and owned by a prominent Chicago designer, is located in one of Islamorada's premier gated neighborhoods, close to shopping and Islamorada's finest fishing fleets. Throughout the house you will find beautiful floors, whimsical décor, and open living room/kitchen. Any family would feel totally at home. The back yard is beautifully landscaped giving you a very private feel. The amazing pool and back porch area is completely screened in, so no pesky bugs. What are you waiting for. This one is going to go fast! If booking more than a year in advance current prices may not reflect 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 b

Located in Islamorada, Florida, United States. Luxurious PH 5BR 3.5BA Gym/ Pool & Jacuzzi/ Sauna Welcome to your luxurious retreat in Islamorada! Experience the epitome of luxury living at our stunning condo located at Mile Marker 75 on the serene Bayside in Islamorada. This stunning 5BR and 3.5BA property is the perfect getaway for you and your group. Featuring a private hot sauna, a wet sauna, and a rooftop area, you'll have plenty of opportunities to relax and unwind. Located in a beautiful area with access to the beach as well as to nearby attractions and activities.The Space:Immerse yourself in luxury and comfort at our expansive 3,500-square-foot penthouse, perfect for a lavish getaway in Islamorada. Unwind in style with ample space to relax and entertain, complete with a private movie theater for cinematic experiences at your fingertips.Master bedroom:Walking closet.Beds: 1 King bed Private bathroom: Shower, toilet, and two sinks. Smart TV. Second bedroom:Closet.Beds: 2 queen bedsPrivate bathroom: Shower with tub, toilet, a

Located in Islamorada, Florida, United States. Your Ultimate Islamorada Hideaway! Full Kitchen, Swimming Pool, 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 upo

Located in Islamorada, Florida, United States. Modern Oceanview Paradise at Islamorada Breathtaking 3bedroom 3bathroom oceanfront vacation home is ready to welcome your family for your next getaway. Enjoy sunrises ad private beach views right from your bedroom. This house was built in 2019, and was only used by the owner. It features all new appliances and has everything you might need for an unforgettable vacation. During your stay, our team will be available for you 24/7 so you can relax and unwind while we make sure your getaway experience is perfect.***notwithstanding anything in the rates page minimal rental is 7 days***

Located in Islamorada, Florida, United States. "Our Happy Place" Paradise in Islamorada with Heated Pool and 90 ft Dock Located in the desirable Islamorada which is know as the “Sportfishing Capital of the World” and where you will find the most beautiful crystal clear waters. The house is just minutes from Channel 5 and Channel 2 which give you quick access to the best ocean and backcountry fishing. You are also just minutes away from a beautiful private beach that you can only access by water. Famous Alligator Reef and Tennessee Reef are just 15 minutes away. This is a beautiful boating, fishing, snorkeling, scuba diving or just relaxing paradise.Within walking distance you have Anne’s Beach. Also, within walking distance you have Caloosa Cove Marina and a convenience store which offer fuel, fishing supplies, bait, etc. You also have the famous Safari Lounge which was recently beautifully renovated.The house can accommodate up to 10 people comfortably. Upstairs you have 3 bedrooms and 3 full bathrooms offering a split plan for pr

Located in Islamorada, Florida, United States. Enjoy a Hassle-Free Stay! 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 card provi

Located in Islamorada, Florida, United States. Charming Beach Front Home in Lower Matecumbe 113 Sunset Drive - Come and stay in this adorable "beachy backyard" home located on the crystal-clear Atlantic Ocean! This home truly has an amazing water frontage. The home has plenty of room for your whole family to relax, having two bedrooms upstairs and two bedrooms downstairs! Near the house is the small Anne's Beach. There are nature trails, boardwalks to a small lunch and BBQ areas, private sandy areas hidden in the mangroves and parking. The home is also near Robbie's Marina (where they feed the Tarpon), Bud n' Mary's Marina and Caloosa Cove Marina. You won't have a problem finding a marina for boat rentals or a fishing guide (Deep Sea or Backcountry). Everything is close! You are only minutes away from "Downtown Islamorada" where Worldwide Sportsman and the Islamorada Fish Company are located yet you are in a quiet area of town. Islamorada Vacation Rental License Number- 24-0387 Per Islamorada's vacation rental ordinances for weekl

Located in Islamorada, Florida, United States. Port Antigua Canal Front Home & Private Beach Get away on Island Time to beautiful Islamorada. Our home is in a lovely quite subdivision with the most beautiful private beach in the FL Keys. Enjoy a screed in porch overlooking the back yard and canal. The screeded in porch has a 6-person dining table, lovely sitting area at the other end. Another open patio is ground level with lots of cozy seating & Grill. Each bedroom has its own access to the porch. A private boat ramp available to launch your boat with some of the best fishing in the Atlantic just minuets away. Plenty of great dinning and actives, many accessible by boat. Property does not come with use of boat lift, minimum space provided for your personal boat.

Located in Islamorada, Florida, United States. Opulent waterfront estate with dock, pool, hot tub & rooftop view - dog-friendly Waterfront WonderOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Swim right up to the edge of luxury at this ultra-private waterfront mansion. Located on one of the most prestigious streets in the Villages of Islamorada, this family-friendly property sits on a sizeable deep-water lagoon with protected boat dockage. Enjoy immaculate indoor/outdoor entertaining space, including wraparound screened balconies with alfresco dining, a heated pool, hot tub, and a fantastic rooftop -- all offering breathtaking vistas.The opulent interior boasts keystone walls, marble flooring, soaring ceilings, and two full kitchens. The chef’s kitchen adds to the grandeur and is fitted with custom cabinets, granite countertops, and stainless appliances like a Sub-Zero fridge and a six-burner gas stove. Sprawl out between three beautifully appo

Located in Islamorada, Florida, United States. Bay front 6BDr Private Beach Pickle-ball Ct Game room Sunset Views This absolutely spectacular bayside estate is available for rentals to the public for the first time. Recently upgraded this 6 - bedroom 5 bath estate will be your gateway to creating memories lasting a lifetime. Newly renovated bathrooms - state of the art kitchen - brand new floors - this is basically a new construction gorgeous estate - this amazing property is located just south of the iconic Robbie's Marina - nestled on 2 acres.*Game room*Ping pong table*Foose ball*Dart board*Poker table*Private pickle ball court*Basketball court*Beach volleyball court ***all courts have lights for night play****Charcoal BBQ*Propane BBQ*Smoker*Fishing off dock*The most memorable Sunset Views in the Florida Keys*Two Tiki huts* Paddleboards*Kayaks*Pools Toys*Wi-Fi*Multiple Big Screen TVs*Gym EquipmentWe offer additional amenities upon request including *Organizing fishing trips*Snorkeling trips**Leisure trips*Sunset boat tours*sandba

Located in Islamorada, Florida, United States. A True Islamorada Oasis with Breathtaking Bay Views Little Bay Compound - 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 equi

Located in Islamorada, Florida, United States. Beautiful 3 Bedroom Condo with Ocean Views Located in Lower Matecumbe Bay Harbour C-312 - Beautiful three bedroom two and a half bath luxury condo at mile maker 74.5. Complex comes complete with two tennis courts, weight room, pool, dockage, fish cleaning station, and Wi-Fi. The condo boasts some amazing views of the Clear Blue waters of the Atlantic Ocean looking over Sea Oats Beach. Relax on your own private roof top patio and enjoy a beautiful sunrise of the glow of a famous Florida Keys Sunset. NOTE: Onsite trailer parking is not allowed at Bay Harbour community. VACATION RENTAL LICENSE: 24-0309 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.If booking more than a year in advance current prices may not reflect 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 proceedi

Located in Islamorada, Florida, United States. Feel the breeze of the keys **HOUSE HAS BEEN RENOVATED AND PICTURES TO COME**Perfect Vacation Home in Islamorada, the center of the Keys Island. The house is ideal for a large family get away, or a small intimate escape. It is perfectly situated between canals providing guests with an unforgettable keys breeze. You are conveniently located near supermarkets, restaurants, and fun activities, like Theatre of the Sea. Take a walk to the community private beach which is only accessible through key access. The house is equipped with 75 total dock space with approximately 35 feet of that dock space to accommodate your boat. It has been updated with a new pool and resort style yard for your enjoyment. Beautiful open views and quick access to ocean. The house is located in one of the most well known fishing areas, Islamorada, renowned for the best fishing areas.

Located in Islamorada, Florida, United States. Your Key to Unforgettable Island Moments! 2 Relaxing Units with Balcony! 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:- These are TWO separate rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms.- The property requires a damage deposit of USD 100/ni