6 BR | 6.5 BA | Sleeps 16 | Quick View
Distance to beach: 0.3 miles to Ft Zachary Taylor
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About this property
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous decks that overlooks the action on ...
Property Type
Key West Villa
2 BR | 2 BA | Sleeps 4 | Quick View
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About this property
Minimum Rental: 28 Days"Beba's Reef House" will capture your imagination the moment you enter the home and rise to the main living level through the reef painted on the walls of the stair well and the photos of fish captured by the owner during numerous dives here in the Keys. This is a ...
Property Type
Tavernier House
2 BR | 3 BA | Sleeps 6 | Quick View
Distance to beach: 0.5 miles to Higgs Beach
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About this property
"MONTHLY" RENTAL ONLY: Old Town Tropical Oasis, Private Pool, Hot Tub, Private Driveway. Meticulously restored and maintained home featuring: 2 bedrooms + den with sleep sofa (can be a 3rd bedroom) and 3 full en suite bathrooms. Our favorite part of this property is the lush & extremely ...
Property Type
Key West House
2 BR | 1.5 BA | Sleeps 6 | Quick View
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About this property
Minimum Rental: 7 DaysSATURDAY to SATURDAY "Moon Bay A206" is calling all fishermen and divers... Whether you plan to fish or dive on your next visit to the Keys, you will find these exceptional accommodations first class and affordable. World famous dive sites are minutes away and phenomenal ...
Property Type
Key Largo Condo
2 BR | 2.5 BA | Sleeps 6 | Quick View
Distance to beach: 0.3 miles to Ft. Zachary Taylor Beach
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About this property
2 Story 2 Bedroom 2 1/2 Bath Townhome in Truman Annex Location, Beauty and Comfort! Kokomo Key has what you are looking for! This upscale home has been meticulously designed with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and beautifully landscaped ...
Property Type
Key West Townhome
1 BR | 1 BA | Sleeps 3 | Quick View
Distance to beach: 0.3 miles to Ft. Zachary Taylor
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Beautifully Remodeled -1BR/1BA End Unit Shipyard Condo in Truman Annex Location, Beauty and Comfort! Southard Breezes has what you are looking for! This gorgeous home has been meticulously renovated with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and ...
Property Type
Key West Condo
4 BR | 2 BA | Sleeps 8 | Quick View
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About this property
Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open from Aug.6th to April 1st. This is a spacious oceanfront home with breathtaking open water views! It is located on beautiful Ramrod Key 85 ft concrete seawall facing the priceless Atlantic ocean teaming ...
Property Type
Ramrod Key House
The home was amazing, plenty of room, lots of fun stuff to do at the home. Beyond amazing cross breezes. Swim spa was really nice. The bikes were great. And the kayaks were a lot of fun. We found lobsters ...
4 BR | 3 BA | Sleeps 8 | Quick View
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Minimum Rental: 28 Days "Palm Harbor" is a spacious elegant home with pool and dock. Gently swaying palm trees greet you at the gated entrance to this wonderful home. The ground level entry features a billiard/game room, bedroom and full bath. An open curved staircase leads to the 2nd ...
Property Type
Plantation Key House
4 BR | 2.5 BA | Sleeps 8 | Quick View
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About this property
Vacation home sits close to the water and has a view over Cudjoe Bay to the Atlantic. Has a private heated pool, 4 bedrooms and 2 bathrooms. Large deck with water access for a boat. Vacation home sits far off of the main road for a great quiet vacation. We have 3 Florida Keys vacation homes on this property. ...
Property Type
Cudjoe Key House
Our stay was perfect! The scenery was beautiful, and the house was very well cleaned and decorated. The manager Steve was very friendly and helpful as well! I would highly recommend this rental to anyone ...
4 BR | 2 BA | Sleeps 8 | Quick View
Distance to beach: 5 miles to Bahia Honda State Park
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About this property
Sorry NO SMOKING or PETS!Minimum 28 days / Please check availabilityGround level 4 bedroom, 2 bath waterfront home on a double lot with a saltwater pool with hot and cold shower, large pool deck and two Tiki Huts. 180 ft of waterfront and 90 feet of dock space with a double fish cleaning table. ...
Property Type
Big Pine Key House
This was a repeat visit for us. We love Big Pine Key and enjoy staying in a quiet neighborhood that's close to fishing, the grocery store and nature trails. The house is very comfortable and the outdoor ...
2 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 1 miles to Sombrero Beach
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Key Lime Sunrise Watch the sunrise & feel the tropical breezes while sipping your coffee from the comfort of the upstairs screened terrace of this lovely and neatly maintained 1,440 sq. ft. two bedroom two & a half bath home situated on Sombrero Beach Road. This charming getaway is within walking/biking ...
Property Type
Marathon House
3 BR | 2 BA | Sleeps 6 | Quick View
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About this property
30 MINUTES TO KEY WEST. BEAUTIFUL LOT WITH COCONUT TREES. BEAUTIFUL BRAND NEW FURNISHINGS. 65" LCD TV IN LIVING ROOM 50" LCD IN MASTER BEDROOM. WORLD FAMOUS LOOE KEY JUST OFF SHORE. TWO QUEEN BEDS AND TWO TWIN BEDS IN THREE BEDROOMS. SONOS MUSIC SYSTEM WITH KLIPSH OUTDOOR SPEAKERS. RELAX IN ...
Property Type
Big Pine Key House
2 BR | 2 BA | Sleeps 5 | Quick View
Distance to beach: 0.3 miles to Port Antigua Neighborhood Beach
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Minimum Rental: 28 Days"West Plaza Del Lago" promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as the exterior! As you enter ...
Property Type
Islamorada House
2 BR | 2 BA | Sleeps 4 | Quick View
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About this property
Minimum Rental: 28 Days"Beacon Reef 222" is an extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. ...
Property Type
Islamorada Condo
3 BR | 3 BA | Sleeps 12 | Quick View
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About this property
MINIMUM STAY: 28 DAYS “Sunrise on Sunset” is the ULTIMATE BEACH FRONT HOME. There are BREATH TAKING OCEAN VIEWS from almost every room in this house! Play in the sand, walk into the ocean or sit under the covered ground level area. This spacious 3BR/3BA single family home offers many ...
Property Type
Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 4 miles to Smathers
Key Amenities
About this property
MONTHLY RENTALS ONLY We purchased Bougainvillea Villa in late 2014 as our future retirement home. The villa was built in the early 1960’s and our neighbors tell us that at one time Jimmy Buffett’s manager owned and lived in the home. It has always been a private home, and was renovated and ...
Property Type
Key West House
Nothing is missing from this very clean and very well organized beautiful home situated on a wide lagoon. For us, the highlight is the superb view of the wide lagoon from the window wall across the entire ...
4 BR | 3 BA | Sleeps 10 | Quick View
Distance to beach: 3 miles to Founders Park Beach
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Minimum Rental: 28 Days"Conch Bar South" is a magnificent home is located at the mouth of a wide canal in Plantation Key and offers phenomenal open water views. The furnishings are new and provide a comfortable and extremely inviting living environment. This 4 bedroom 3 bath single family ...
Property Type
Tavernier House
2 BR | 2.5 BA | Sleeps 6 | Quick View
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Seaglass-Paradise on the Gulf is located in the heart of the the beautiful Florida Keys. The Keys are a series of 40 islands connected by 40 bridges , off the southern most tip of Florida. The chain of islands extends 120 miles into the Atlantic Ocean and Gulf of Mexico. The area is famous for its Caribbean ...
Property Type
Marathon Condo
3 BR | 2 BA | Sleeps 6 | Quick View
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About this property
Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, and dockage for your ...
Property Type
Islamorada Condo
My family and I had a great time in the Florida Keys this year. I have family that moved there in the last year or so and we wanted to visit. It was amazing!! We really had a great time and I was so happy ...
4 BR | 3 BA | Sleeps 8 | Quick View
Distance to beach: 9 miles to Bahia Honda State Park & Beach
Key Amenities
About this property
Welcome to paradise! Come experience the amazing Keys and beautiful open water home with 200 foot long dock for your boat. Exclusive heated pool to relax and enjoy the surrounding ocean view - just breath taking! The private lot is .81 acre with one other rental and still very spacious. Stunning panoramic ...
Property Type
Little Torch Key House
Enjoyed every minute....great layout and even better for the watercraft...thank you.
4 BR | 3 BA | Sleeps 10 | Quick View
Distance to beach: 4 miles to Sombrero
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About this property
Lovely, oceanfront 4 bedroom, 3 bath home. The main house is three bedroom, two bath with the kitchen, living and dining area. The master bedroom has a king size bed, the first guest bedroom has a queen and the 3rd bedroom has two sets of bunk beds with full size on the bottom and twins on the top. Then ...
Property Type
Marathon House
We thoroughly enjoyed our stay at this vacation home. There are a few things that could be addressed. However our overall consensus was a very positive experience! We would stay here again.
4 BR | 4 BA | Sleeps 8 | Quick View
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On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool, or combines for a wonderful four bedroom retreat.Downstairs there is a large, open floor plan with living ...
Property Type
Key West House
2 BR | 2 BA | Sleeps 5 | Quick View
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Minimum Rental: 28 Days "The Palms #309" is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen ...
Property Type
Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
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Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory which is now restored ...
Property Type
Key West House
5 BR | 4 BA | Sleeps 12 | Quick View
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About this property
Imagine gazing across a large, sparkling swimming pool to see a natural in-ground aquarium... big enough to swim in, and filled with tropical fish. The dock accommodates large boats drawing 5' + and you have instant access to Florida Bay, the Gulf and the Atlantic. The sunset views here are endless, and ...
Property Type
Grassy Key Estate
2 BR | 2.5 BA | Sleeps 6 | Quick View
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About this property
MINIMUM STAY: 28 Nights. Bayfront townhouse located in the lush tropical setting of Rock Harbor Club in Key Largo. You'll love the open water views from the two oversized screened balconies - one off the main living area and the other off the master suite. There's something for everyone at Rock Harbor ...
Property Type
Key Largo Townhome
2 BR | 2.5 BA | Sleeps 6 | Quick View
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About this property
COZY VILLA WITH YOUR OWN PRIVATE SPA OVERLOOKING BLUE WATER LAGOON TWO BEDROOM 2 1/2 BATH VILLA QUEEN BEDS WITH PILLOW TOP MATTRESSES, VERY COMFORTABLE QUEEN PLUS SOFA BED. VILLA SLEEPS SIX COMFORTABLY. EACH BEDROOM HAS SEPARATE BATH WITH TUB/SHOWER AND TV. FULLY EQUIPPED KITCHEN TO COOK YOUR ...
Property Type
Duck Key Villa
The place we stayed was absolutely gorgeous! Everything was clean and in working order. Location was great because we were able to go south to Key West if we wanted and also North to a few areas we wanted ...
2 BR | 2 BA | Sleeps 4 | Quick View
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About this property
Tropically furnished, privately owned condominium at the Futura Yacht Club in the Village of Islamorada. Futura Yacht Club is a gated community located on the Gulf of Mexico and consisting of 70 units. Enjoy your morning coffee watching the boats go out. Relax with a amazing sunset and a glass ...
Property Type
Islamorada Condo
4 BR | 3 BA | Sleeps 10 | Quick View
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About this property
"SOMBRERO HEAVEN" ~ Brand New, Designer Decorated and Perfectly Appointed 4-Bedroom (1 King, 3 Queens), 3-Bath Private Heated Pool Villa with Neighborhood Ocean Front beach and Second Story Screened Balcony that Over Looks Private Pool and Canal! Everything you need for the perfect keys vacation ...
Property Type
Marathon Villa
2 BR | 2.5 BA | Sleeps 6 | Quick View
Distance to beach: 5 miles to Sombrero Beach
Key Amenities
About this property
Entering our luxurious condo, you will be impressed with expansive ocean views, literally from every room. Corner-sited and on the 1st floor (above parking), the wrap around private balcony, with all-new wicker lounge furniture, is but a stone toss to the ocean. Travertine tile floors and granite counters ...
Property Type
Key Colony Beach Condo
3 BR | 2 BA | Sleeps 6 | Quick View
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About this property
Clean, Tropical 3/2 on open canal in quiet residential neighborhood on a cul-de-sac. House is on Gulfside with quick access to Miles Channel Bridge towards ocean or bayside. 50’ concrete dock with fish cleaning station and shower.Master Bedroom has a queen size bed, shower and indoor jacuzzi ...
Property Type
Ramrod Key House
2 BR | 1 BA | Sleeps 4 | Quick View
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About this property
Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island.Enjoy full use of direct TV channels, free current video library ...
Property Type
Key West House
5 BR | 4 BA | Sleeps 12 | Quick View
Key Amenities
About this property
Located on the Highly sought after Sombrero Beach area of Marathon, which is the beginning of the lower keys just 50 min from Key West is our Florida Keys Tropical Paradise . Less than a third of a mile to the Sombrero Beach and the Sombrero Beach Park, With a deep water concrete dock with ocean access ...
Property Type
Marathon House
Very nice, quite place! With lots of extras, We enjoyed the pool, water dock and the view! We recommend this location!
2 BR | 2.5 BA | Sleeps 6 | Quick View
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“Ocean Breeze” – This Beautiful Condominium Features an Ocean view, Protected Boat Slip, Tennis, Gym, and much, much more.New to the Vacation Rental market, this 2 Bedroom condo at Bay Harbour has been outfitted to make a Statement. Easy access to the Gulf or Ocean makes this ...
Property Type
Islamorada Condo
3 BR | 3 BA | Sleeps 8 | Quick View
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About this property
Minimum Rental: 28 Days "Blue Water Retreat" is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from ...
Property Type
Islamorada House
Key Amenities
About this property
This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The patio overlooks ...
Property Type
Key West Condo
4 BR | 4 BA | Sleeps 10 | Quick View
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About this property
This beautifully furnished waterfront home with ocean views will thrill the most ardent diver or fisherman and his family. You will love the luxury of a heated pool, magnificent view, and protected deep water dockage for multiple boats. It is located on a large harbor with multiple sailing yachts and ...
Property Type
Islamorada House
4 BR | 3 BA | Sleeps 10 | Quick View
Key Amenities
About this property
MARATHON ANGLER'S RETREAT in Marathon is a brand new property with every modern convenience and a warm coastal decor! Located right on a canal (just 15-20 minutes from open water) it has its own private dock (can accommodate up to a 45' boat on a 30' dock), fish cleaning station, hot tub and two single ...
Property Type
Marathon Villa
3 BR | 2 BA | Sleeps 10 | Quick View
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About this property
Minimum Rental: 28 Days"Gulfview Getaway" is a FABULOUS BEACH FRONT HOME! This is what you've been dreaming of - your very own single family home with a private sandy beach in the Keys. This home is new to the rental market. It is located in a highly desirable area of Islamorada on ...
Property Type
Islamorada House
4 BR | 3 BA | Sleeps 8 | Quick View
Distance to beach: 0.9 miles to Cabana Club
Key Amenities
About this property
ENJOY OUR HOME with 5 STAR REVIEWS & New TIKI HUT, Open Water Access 5 minutes NEW WHITE kitchen with QUARTZ COUNTERTOPS, NEW STAINLESS STEEL APPLIANCES (photos coming soon),Perfect home for a Family Gathering, or Extended Family Get Together, or Families traveling together. Boater's perfect ...
Property Type
Key Colony Beach House
4 BR | 4 BA | Sleeps 10 | Quick View
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About this property
Cock-a-doodle-do Vacation Rental, named for Key West's beloved chicken population, is a mid-town oasis! 5 minute drive to Old Town or take Uber for just $ 10!A meticulously updated pool home with beautifully lush landscaped grounds and plenty of space for everyone! The main house is a 3/3 (1 King, ...
Property Type
Key West House
Key Amenities
About this property
Lovely three bedroom, three bath home with 48' of deep water dockage just moments to the Gulf. 110 electric at the dock area. Lovely newer home with 5 flat screen TV's, including a 60" in the living room and a 36" in the master. Premium TV w/HBO. Lovely pool area with bar seating, and the ...
Property Type
Marathon House
3 BR | 2.5 BA | Sleeps 6 | Quick View
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About this property
A relaxing executives delight -High-end Estate overlooking tranquil 'Bonefish Flats' in picturesque Marathon. Designer decorated with contemporary colors, loads of fine architectural details, Crema Marfil marble, Granite, Hardwood floors, open air porches and balconies. This is a superb, secluded estate, ...
Property Type
Marathon Estate
This is both a unique and well-run property. Lisa is very accessible and responsive. I left something very valuable here, and before I even realized it Lisa had told me it was found and wanted to know where ...
2 BR | 2 BA | Sleeps 4 | Quick View
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About this property
Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. PHOTO UPDATES COMING SOON. "Beacon Reef 522" offers magnificent 180 degree oceanfront views. Enjoy the sea breezes as your relax on your private balcony and gaze at the water. Whether staying one month or more you will be more than happy ...
Property Type
Islamorada Condo
1 BR | 1 BA | Sleeps 4 | Quick View
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#41 Windley Key RV Park84961 Old Overseas Highway Islamorada, Florida Keys 33036 1 bedroom + sleeping loft. $2900 per month includes all utilities. Available 7/1/19. Minimum rental period is one month, longer term preferred. Rental also includes a 23’ boat dock and ramp. Community jetty ...
Property Type
Islamorada Mobile Home
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 8 miles to BAHIA HONDA
Key Amenities
About this property
Big Torch Key is reminiscent of the Keys 40 years ago, seclusion and peace invade your senses immediately, sunset views will take your breathe away. Located on 1.4 acres on Niles Channel, in National Key Deer Refuge, the best boating access to the Atlantic (2 miles) and the Gulf (6 miles) in the lower ...
Property Type
Big Torch Key House
Torchview is heaven, beautifully landscaped, we enjoyed the Key Deer, fantastic sunsets and ocean treasures. My grandson loved fishing on the pier, it was wonderful to be with family for a week at Torchview. ...
3 BR | 3 BA | Sleeps 8 | Quick View
Distance to beach: 1 miles to Coco Plum & Sombrero Beach
Key Amenities
About this property
This new gated Marathon home is 2 levels with an elevator. 3 Bedroom / 3 Bathroom , Sleeps 8 people, with all the comforts of home. This home offers nothing but the best in home furnishings and security. Panoramic water views from private decks off the living room and master bedroom. Master / King bed; ...
Property Type
Marathon House
Larry has the most beautiful, restful and comfortable vacation home ever. He thinks of everything to make your stay the best ever. Very clean and all the comforts you could ever ask for.
4 BR | 3 BA | Sleeps 10 | Quick View
Key Amenities
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This spectacular home has everything you will need to enjoy paradise! Situated in a very quiet and desirable neighborhood close to the beach and shopping. This home is a private oasis with mature landscaping on both sides, the golf course on the street side and only mangrove fringe across the canal. private ...
Property Type
Marathon House
4 BR | 4 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Venetian Shores 4-Bed/4-Bath Luxury Pool Home with 100' Dock & Opt. ElevatorMINIMUM STAY: 29 DAYS Dreaming of a Florida Keys vacation where you can boat, fish, dive, snorkel, or stay home and swim in your own private heated pool? This is it. This home offers a professionally-designed living environment ...
Property Type
Islamorada House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Minimum Rental: 28 Days"Beacon Reef 310" is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your ...
Property Type
Islamorada Condo
