Key Amenities
About this property
Beautiful oceanfront apartment with easy access to pool, spa, and beach. Dock with boat slips and tiki hut overlooking the Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs ...
Property Type
Islamorada Condo
Key Amenities
About this property
One of the only white sandy beaches in the Fl Keys and 1 mile whole of it!Newly built,state of the art,beautifully done 5 bedroom home, 4 master suites w/ king beds and facing open water! Magnificent indoors and out! Each bathroom is exquisite,very large stone,glass and hand picked tiles. The ...
Property Type
Islamorada House
3 BR | 3 BA | Sleeps 6 | Quick View
Distance to beach: 2 miles to Anne's Beach State Park
Key Amenities
About this property
This stunning top floor end unit in Bay Harbour has stunning ocean and harbor views from every room and includes a 50ft. boat slip and a 25,000# lift. BAY HARBOUR ALLOWS 7-DAY RENTALS. The interior design is spectacular. Coffered ceilings in the living area, top of the line Miele and Thermador appliances, ...
Property Type
Islamorada Condo
We have stayed at Bay Harbour before, but this was our first time renting this unit and it was absolutely perfect. The location and water views are wonderful, and the inside of the unit is beautifully decorated. ...
3 BR | 2 BA | Sleeps 10 | Quick View
Key Amenities
About this property
''BEAUTIFUL BAYFRONT PROPERTY!!!!''** 2022 Remolded bathrooms, 2021 NEW POOL** Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 8. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath. Entire house ...
Property Type
Islamorada House
This was our 4th year on Tollgate and somehow it gets better. Tiff and Bill go above and beyond in accommodating us. The updates look fabulous, love the painting in the dining room. Our dog Max has made ...
3 BR | 3 BA | Sleeps 6 | Quick View
Key Amenities
About this property
This home has a private beach entrance directly into the bay and is across from Sea Oats Beach. Enjoy a quick paddle board or kayak trip directly out of the back door. Dock and boat lift avialble for 30+ foot boat. Unmatched views of both the Atlantic Ocean, Gulf ocean or both from every window and ...
Property Type
Islamorada House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Distance to beach: 0.5 miles to White Marlin Beach
Key Amenities
About this property
Bring your boat and Jet SkisNestled on a canal, less than a 2 minute boat ride to the bay and 10 minutes to the ocean with key access to private White Marlin Beach. New heated pool and hot tub, 70' dock with fish cleaning table, commercial ice machine, double jet ski lift, and two floors facing ...
Property Type
Islamorada House
We stayed in this home for a month, the location is amazing if you love to paddle board, kayak and discover the many mangrove islands that are a five minute paddle from your dock. The outside area has ...
4 BR | 2 BA | Sleeps 12 | Quick View
Key Amenities
About this property
ALERT: BRAND NEW POOL JUST COMPLETED AND INSTALLED....DOWNSTAIRS IS AVAILABLE TO RENT BUT IS NOT INCLUDED IN THE PRICE feel free to ask about downstairs pricing and availability. Downstairs is an additional 3br and 2ba so the upstairs and downstairs would be a total of 7br & 4ba....THIS LISTING ...
Property Type
Islamorada House
My wife and I spent the month of Dec. 2022 at this property in Islamorada (HEAVEN) in the Keys. The property has a pool, a canal and a boat dock that can handle any boat.Let me start of saying that ...
6 BR | 7.5 BA | Sleeps 12 | Quick View
Distance to beach: 1 feet to on property
Key Amenities
About this property
COMING SOON - Beautiful new home on Florida Bay with sandy beach, large pool, beautiful views and sunsets all year round. Private suites are offered for 2-6 people each with king bed, private bath and mini kitchen facilities. Possible to handle large groups up to 12 adults. Estimated availability late ...
Property Type
Islamorada House
3 BR | 2 BA | Sleeps 10 | Quick View
Key Amenities
About this property
Newly renovated 3/2 Canal front home with brand new pool, deck and front gates for privacy!The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra clean and has modern furnishings. It has 3 bedrooms, 2 baths. Upstairs there are 2 bedrooms, ...
Property Type
Islamorada House
2022 was our 2nd time renting this wonderful home. The location is fantastic, and the house and property offer everything you can imagine. Outside is a paradise with a refreshing pool (with fun lights ...
2 BR | 2 BA | Sleeps 4 | Quick View
Distance to beach: 1 miles to Anne's Beach State Park
Key Amenities
About this property
This Condo sleeps 4 and comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key, Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks. Newly refurnished and refurbished, ...
Property Type
Islamorada Condo
This 5th floor condo did not disappoint. The double balcony offered great views of the bay, and a spiral staircase up to the private roof top was another great place to watch the spectacular sunsets. The ...
2 BR | 2 BA | Sleeps 4 | Quick View
Distance to beach: 100 feet to Front door
Key Amenities
About this property
MINIMUM STAY: 30 daysSpacious and beautiful 2 bedroom/2 bath ocean front condo unit with unobstructed ocean views. BOAT SLIP is available upon request for up to a 46 foot boat, low tide draw is 30 inches. There is an additional fee for boat slip.Walk out your front door and go boating.You’ll ...
Property Type
Islamorada Condo
4 BR | 4 BA | Sleeps 8 | Quick View
Key Amenities
About this property
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 ...
Property Type
Islamorada House
Key Amenities
About this property
Welcome to the “Sailfish House” at Tarpon Point!Soak up the sun and take in the spectacular views at this opulent 4 bedroom, 4 bath home located in the private community of Tarpon Point. Accommodating up to eight adults, this impressive home makes it easy to both entertain and unwind with ...
Property Type
Islamorada House
Key Amenities
About this property
This Condo is located on Lower Matecumbe Key, close to restaurants, shopping and Tiki bars. With pool, tennis courts and a protected marina, Bay Harbour is a preferred residence for repeat visitors to the Keys. Elevators for easy access and a second floor location make it easy to enjoy your stunning view ...
Property Type
Islamorada Condo
The condo was lovely! Thoroughly furnished. Updated amenities. Beautiful grounds. On-site staff. Friendly and helpful. Highly recommended
1 BR | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
The Jetson's House apartment (Located on the prestigious White Marlin Beach - which is considered one of the nicest natural sand beaches in the Florida Keys) features great swimming, snorkeling, and spectacular sunsets right off the beach! Have fun exploring an artificial reef! What makes the beach ...
Property Type
Islamorada Apartment
The location of this apartment is amazing. You are right on the ocean with a very private beach directly out your front door. We spent many days on the lounge chairs enjoying the view and listening to ...
2 BR | 2 BA | Sleeps 8 | Quick View
Key Amenities
About this property
1440 sf - Sleeps 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 ...
Property Type
Islamorada House
Here is the review I am trying to post via for our March 2024 stay.Wonderful! Fantastic! Amazing!Wonderful Hosts!!! Jay and Sharon are so welcoming and supportive! We felt at home before we ...
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 7 miles to Anne's Beach State Park
Key Amenities
About this property
This 3-bedroom condo couldn't be any closer to the ocean. Located on the 4th floor at Palms of Islamorada this unit takes full advantage of the waterfront setting. There are two bedrooms with open water views overlooking the blue waters with Alligator lighthouse off in the distance. Both of these ...
Property Type
Islamorada Condo
This unit far exceed our expectations. Beautiful decor, ocean views, pool, clubhouse, all were top notch. Management team very responsive, had an issue with door lock and was immediately resolved. Great ...
3 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
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 ...
Property Type
Islamorada Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Key Amenities
About this property
Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys.Huge ocean front dock with plenty of room for fishing! Wifi, deluxe cable, and restaurants within walking distance.2 ...
Property Type
Islamorada Condo
Plantation by the Sea is an older condo complex that is beautifully maintained. The condo is located at MM 87.5 just off of U.S. 1 in the heart of Islamorada. Restaurants of various types can be found within ...
4 BR | 4 BA | Sleeps 10 | Quick View
Distance to beach: 2 miles to Founders Park
Key Amenities
About this property
This tropical waterfront beauty has it all...heated pool, spa, dock and custom elevator. Beautifully appointed and fully equipped for your ultimate holiday rental. Located on a deep water canal with direct access to the Bay or Ocean. Enjoy unforgettable sunsets while relaxing on one of several patios ...
Property Type
Islamorada House
If you’re looking for a well kept beautiful home, right on the water positioned right between the Gulf and Atlantic, great pool and hot tub YOU FOUND IT. Communication is great and owner is so helpful. ...
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Large two bedroom, two bath, two balcony condo. Brand new King sized bed frame in master bedroom with a peekaboo ocean view from balcony and a large walk in closet. Guest bedroom also has a king sized bed and balcony with peekaboo views of the ocean. Living room features a brand new pull out sofa. Condo ...
Property Type
Islamorada Condo
We stayed here in Nov. Weather was great.Condo is located 5 mins.from Founders Park.Check out Founders Park online. Owners can give you more info about securing a pass for entry. Condo is close to shopping, ...
Key Amenities
About this property
This Condo comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks.
Property Type
Islamorada Condo
Key Amenities
About this property
Beautiful, fully remodeled waterfront home with water on both sides! Ocean and lagoon views from bedrooms, dining room, balconies and kitchen. Cable TV with premium channels and wi-fi internet access. The home is in a quiet neighborhood on a cul-de- sac and very convenient to Tavernier or Islamorada ...
Property Type
Islamorada House
A well maintained home in a perfect quiet setting. The owner Patrick was outstanding to work with and made sure that all was in order. He is an excellent communicator. Welcome bottles of wine greeted us. ...
6 BR | 4 BA | Sleeps 12 | Quick View
Distance to beach: 0.5 miles to Port Antigua Private Beach
Key Amenities
About this property
This recently renovated property enjoys 6 bedrooms, 4 bathrooms and separate kitchens, living rooms and laundry facilities. It shares an ocean facing veranda with 2 dual gas grills and multiple seating and lounging areas. It has ample offstreet parking for vehicles and trailers. The Admiral on the Cove ...
Property Type
Islamorada Townhome
We enjoyed our stay at this beautifully furnished and well stocked house. George and Bonnie responded quickly to any questions that we had. The separate living areas allowed us to enjoy family and friends ...
Key Amenities
About this property
The apartment is in a house on the canal and across from the beach with beach access. It is situated on the ground floor of a two storey Keys house where you would be the only residents. All the amenities would be yours and you would have space, tranquility and privacy in the tropically planted landscape. ...
Property Type
Islamorada Apartment
This is the perfect apartment for one couple. Wonderful location on the oceanside with ocean views across the street. Has a great dock for your boat with great ocean access. Fish cleaning table is under ...
Key Amenities
About this property
Welcome to Paradise Palms!Located on a cul-de-sac in the charming city of Islamorada, this beautifully- appointed five-bedroom, four and a half-bath home serves as an excellent setting for your tropical getaway. Ideally located in Islamorada on Lower Matecumbe Key, you will have convenient access ...
Property Type
Islamorada House
3 BR | 3 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Welcome to “At The Sandbar!”This newly built oceanside villa in Islamorada is a wonderful choice for those seeking a serene retreat and an opportunity to immerse themselves in the relaxed nature of the Florida Keys. Situated within the Peaceful Palms community on Windley Key, this three-bedroom, ...
Property Type
Islamorada Villa
1 BR | 1 BA | Sleeps 4 | Quick View
Distance to beach: 0.3 miles to Anne's Beach
Key Amenities
About this property
Enjoy this modern lagoon front ground level one bedroom condo/apartment with exclusive use of the backyard, pool, dock and carport. Located on the Gulf side of Lower Matecumbe (Islamorada MM 73.5) minutes from the Channel 2 and Channel 5 Bridges offering immediate access to Ocean side. Dockage available ...
Property Type
Islamorada Condo
After staying in St. Pete Beach for a month, we decided to go south and visit the Florida keys. We found Bill and Carolyn's place on Florida Rentals and decided to give it a go. What a wonderful experience!The ...
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 2 miles to Anne's Beach State Park
Key Amenities
About this property
This updated Port Antigua home with 85 ft. of concrete dock is ready for a new family to enjoy. The open floor plan and vaulted ceilings make this house feel so welcoming! French doors with side lights let in the natural light and open to the lanai where you can enjoy your morning coffee or a cocktail ...
Property Type
Islamorada House
6 BR | 5 BA | Sleeps 14 | Quick View
Key Amenities
About this property
Welcome to Caribee Beach House!This estate is the perfect mix of old school Islamorada combined with present-day, stylish luxuries. This hidden gem is a special slice of heaven, nestled in downtown Islamorada, boasting with 200 feet of exclusive water frontage, 100’ dock, and fabulous views ...
Property Type
Islamorada House
4 BR | 2 BA | Sleeps 8 | Quick View
Key Amenities
About this property
4 Bedroom 2 bath home with private dock and private pool with direct open access to the ocean and convenient access to the bayside through Tavernier Creek. This is both family-friendly and a fisherman's dream. Our home sleeps 8 with every comfort you would want while on vacation in the keys...Large ...
Property Type
Islamorada House
Key Amenities
About this property
Facing due west this property takes full advantage of the spectacular sunset view over the bay. GreenFlash has a bayside infinity pool and dockage to help you take full advantage of the myriad of water activities available in Islamorada, the 'Sport Fishing Capital of the World.' The two story ...
Property Type
Islamorada House
2 BR | 2 BA | Sleeps 4 | Quick View
Distance to beach: 0.9 miles to Founders Park
Key Amenities
About this property
Oceanfront gated community. Offers pool overlooking the ocean, pier which you can fish off of, clubhouse, sauna, exercise room, and very clean bathrooms by the pool. 2 Bed, 2 Bath. Master bedroom offers queen bed, sitting room, coffee, 50 inch smart tv, storage, master bath separate toilet. 2nd Bedroom ...
Property Type
Islamorada Condo
Sharon’s condo was absolutely gorgeous! It was super clean upon arrival and had everything we could have needed for our 3 month stay (linens, dishes, pots & pans, cleaning supplies, etc). The interior ...
2 BR | 1 BA | Sleeps 5 | Quick View
Key Amenities
About this property
Welcome to the "Keys Life Cottage!"This beautifully updated and spacious two bedroom, one bath home is tucked away on a large landscaped lot in the heart of Islamorada and within walking or biking distance to Islamorada's famed Arts and Cultural district and to some of the most renowned ...
Property Type
Islamorada Cottage
2 BR | 2.5 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Experience total seclusion in this ten-unit oceanfront complex called Port of Call, nestled between the mansions of Millionaire's Row in Islamorada on the Atlantic Ocean, Mile Marker 88.Outdoor facilities include a heated pool; chickee hut with common area barbecue grills, and a small sand beach. ...
Property Type
Islamorada Townhome
Key Amenities
About this property
Mile Marker 75 – Bayside4 bedroom 3 bathPalm Cottage South, is a charming, modern home directly on the canal with a heated, private pool, dockage, and access to the Port Antigua community sandy beach. Dockage for 24′ boat max on the lift pictured.Elevated for great breezes and ...
Property Type
Islamorada Villa
Great house, pool, and area. Lots of attractions and wonderful restaurants. Also, great people to work with.
4 BR | 2.5 BA | Sleeps 11 | Quick View
Key Amenities
About this property
This charming, island style beach house on Lower Matecumbe Key is the perfect spot for your next Florida Keys vacation. This home can sleep up to 11 guests, with 4 bedrooms and 2 1/2 baths. The main living space features a fully equipped kitchen and an open floor plan with vaulted ceilings, tons of natural ...
Property Type
Islamorada House
We loved Harbor Hideaway for our month long getaway to Islamorada. The home is beautiful with gorgeous sunset views and huge private balconies. The newly renovated bathrooms are fantastic! The outdoor ...
1 BR | 1 BA | Sleeps 2 | Quick View
Distance to beach: 1 miles to Anne's Beach
Key Amenities
About this property
Secluded Waterfront Apartment with Tiki hut, dock, King bed, 1 Bath, Sleeps 2.Please contact us for all of our rates for different length of stays! For shorter stays, make sure you have a minimum of 28 days entered in your contact form! We do not use the rate feature or the calendar feature on this ...
Property Type
Islamorada Apartment
We stayed two weeks in the beautiful apartment and it was the best vacation ever! Chris is a wonderful host, very friendly and a wealth of information about the area! We will be back next year!
3 BR | 2.5 BA | Sleeps 6 | Quick View
Distance to beach: 2 miles to Founders Park
Key Amenities
About this property
Welcome to your dream getaway in Islamorada! This 3-bedroom, 2.5-bath paradise boasts a gourmet kitchen with a Viking gas stove, a spacious dining area, and Internet-ready TVs for game days or movie nights.On the first floor, you will find two bedrooms, a full bathroom and a large entertainment area ...
Property Type
Islamorada House
My family and I stayed in this house and everything was absolutely perfect. The house was very clean and the backyard is very spacious for tanning and enjoying the warm sunny weather. I will definitely ...
4 BR | 3 BA | Sleeps 10 | Quick View
Key Amenities
About this property
This gorgeous, newly constructed, Islamorada home has 4-bedroom, 3+ bath and is located in the quiet neighborhood of Venetian Shores MM86. It provides immediate access to both the Atlantic Ocean and Florida Bay via Snake Creek.The deep-water dockage is ideal for the avid boater or fishing enthusiast. ...
Property Type
Islamorada House
This was a great house! Our whole family enjoyed the stay very much. It was quiet and the layout of the home is perfect for multiple families to stay. The pool area was very nice and the dock is a perfect ...
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Gorgeous updated 2 bedroom, 2 bathroom condo with large modern kitchen in an oceanfront gated building with oceanfront pool, fishing dock, gym, sauna, barbecue grills and so much more, and the best part is YOU'RE IN THE FLORIDA KEYS!
Property Type
Islamorada Condo
Great condo, pool, and neighbors. Highly recommend. The pool is heated. Ocean view is great. Community room. Has exercise room and sauna.
1 BR | 1 BA | Sleeps 2 | Quick View
Distance to beach: 5 miles to Founders Park
Key Amenities
About this property
Half Duplex HomeAre you seeking a beautiful hideaway close to all the amenities? This delightful 1 bedroom half duplex vacation home has deep water dockage for your boat in the back yard with the view of a beautiful lagoon. This lagoon has schools of tarpon to test your angling skills, and manatees ...
Property Type
Islamorada House
The screened in area and the outdoor space make this rental perfect! We kayaked on the canal, and walked around the neighborhood daily. We watched boats and manatees from the screened in porch. Lee (the ...
Key Amenities
About this property
Mile Marker 75 – BaysideLarge, modern 4 bedroom canal front home with pool in Lower Matecumbe Key in Islamorada, Florida Keys. This gorgeous home overlooks the pool and canal.The main selling point of Latitudes is the home’s awesome outdoor area. Pool, Tiki Hut, grill and outdoor seating ...
Property Type
Islamorada House
Key Amenities
About this property
MM 87.7 . 2 Bedroom & 2 Bath. Rented 28 days minimum Experience the epitome of oceanfront luxury in this exquisite paradise! Delight in fishing the pristine waters of the Keys with the convenience of your own 30ft slip in a secure marina. Unwind in the comfort of your spacious condo that boasts ...
Property Type
Islamorada Condo
2 BR | 2.5 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Breathtaking Waterfront 2/2.5 Townhouse In Desirable Futura Yacht Club. Lots of outdoor living space,great for entertaining and enjoying the magnificent unobstructed Bayviews and beautiful sunset! Futuravis a gated community with a large pool tennis courts, boat ramp,beach and boat/trailer storage,parking ...
Property Type
Islamorada Townhome
3 BR | 3.5 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Islamorada waterfront gem located on Sandy Cove Basin with total renovations completed in 2024. New pool and spa, new deep water dock. Three en suite king bedrooms. Nicely appointed kitchen. Private gated and fenced yard with ample parking.
Property Type
Islamorada House
Key Amenities
About this property
SPECIAL SUMMER SALE RATES MAY-JULY!! SEE SPECIAL POSTED RATES MAY-JULY! 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. ...
Property Type
Islamorada Condo
4 BR | 4.5 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Immerse yourself in the luxury and beauty of Oceanside, a brand-new gated community with 9 beachfront homes nestled in the heart of Islamorada. Our 4 bedroom home invites you to experience modern coastal comfort while its nearly 3000 square feet of indoor space provide ample room for family and friends. ...
Property Type
Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 2 miles to Founders Park
Key Amenities
About this property
Experience high-end coastal luxury while staying at “Sea Breeze 41” in the highly sought-after Coral Harbour Club Condominium (CHC) . Your spacious 3 Bedroom / 2 Bathroom island getaway exudes luxury tropical vibes and is professionally decorated in Tropical Modern style. A 30' Boat Slip ...
Property Type
Islamorada Condo
Key Amenities
About this property
This is a cute cottage all remodeled white tiled, waterfront in the secluded neighborhood of Plantation Key Colony The house offer two bedrooms one with a king size bed and the second with two full beds A complete remodeled kitchen galley type with all appliances and many kitchen gadgets, spices and ...
Property Type
Islamorada Cottage
Mercy and Jose’ have a beautiful home that we have been able to rent for 4 months during the months of Jan- April! They take great care of their home and they respond very quickly if you need to reach ...
