Houses Florida Keys

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892 houses

3BR Oasis in the Keys w/ Kayaks & Paddle Boards - Sweeping Ocean Views!

Marathon house

3 bedrooms / 2 bathrooms / sleeps 8

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$303

Lovely condo with stunning ocean views & entertainment - close to the beach!

Duck Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 51 minutes

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$134

Keys Cove Home #2 The Reel World

Marathon Shores house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 38 minutes

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$490

Canal-Front 3BR w/ Private Pool, Boat Slip, Tiki Hut & Kayaks - Near Beach

Marathon house

3 bedrooms / 2 bathrooms / sleeps 6

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$158

Relaxing retreat with full kitchen and amazing ocean views!

Duck Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 49 minutes

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$134

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

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$1,717

SPECIAL FALL RATES, INCL. LABOR DAY - BOOK NOW!

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 5 minutes

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$288

75731 Overseas Highway

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

“Vacation of a lifetime!” I can't say enough good things about this home. It was beautiful, clean, and peaceful. The only thing that might be considered a down side is that all of the bedrooms are located upstairs, but that was not a problem for us. Brandi at Freewheeler Realestate was wonderful. She was prompt with answers to questions, friendly and professional. The home-owner obviously wants to see to it that the people staying in their home are well taken care of. Everything was great all the way down to the fluffy beach towels. We will definitely look at staying at this home again.

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$1,227

Oceanfront condo w/beach access, shared tennis, pool, etc. - marina available!

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 51 minutes

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$89

Private Home, with Beach Access, Best Value in the Keys

Key Largo house

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect house for casual getaway” We wanted a clean and comfy place to stay for a long weekend that would be close to everything. This house had everything we wanted and more. We brought our 2 year old with us and felt like it was exactly the cozy and safe place we needed. If we weren't relaxing on the front or back deck, there were a number of board games that entertained us while our child napped. The owner was pretty quick to respond to any questions we had. We hope to stay here again for future getaways!

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$75

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 1 hour 17 minutes

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$257

PARADISE OCEAN FRONT HOME

Marathon house

4 bedrooms / 3 bathrooms / sleeps 12

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$286

Waterfront Keys Home - Spectacular View, 37' Dock

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful location” My husband, son, and I had a fantastic vacation here. The private boat dock and Bay Area was perfect for our needs. We were out in the gulf in a few minutes and could reach the Atlantic via Vaca Pass or 7 Mile bridge in just a short boat ride. The house itself was the perfect size for the 3 of us(& 2 shelties), giving each of us our own space. The view from the house is great. We watched tarpon, turtles, and dolphin!! The airport right behind us was not an issue!! In fact, we thought it was kind of cool to watch some of planes/helicopters!! The storage area with the bait fridge/freezer was a great plus!! There were 2 things that I noticed could improve (but by no means a reason to not stay here!!). First there was not any pantry storage. We just used the island top. No big deal. And the lint screen for the dryer was falling apart. Again no big deal. I would not hesitate to stay here again!!

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$143

Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 12 minutes

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Price per night from

$315

Paradise on the water

Key Largo house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 8 minutes

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$291

FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 8 w/ 60 Feet of Dockage

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 13 minutes

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$258

75130 Overseas Highway

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 4

“The view and location was excellent.” The house had most of the amenities I would expect at a beach location. You can't beat the sunsets over the bay! We snorkeled at Key Largo and took a day trip into key West, so the location was perfect. The area had the best restaurants. We tried them all. Only complaints were: no outdoor grill, no wine glasses, sheets kept pulling off the bed and rusted beach chairs.

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$190

Waterside Bay

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

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$196

Key Largo Kampground Vacation

Key Largo house

1 bedroom / 1 bathroom / sleeps 3

“Great location and pleasantly surprised!” Romberto's Camprground vacation was definitely more than i expected. There was ample room for my husband and I, the folks were nice and the area was quiet and clean. The marina was convenient (small boats only). There was a small leak in the bathroom in the overhead skylight but it was almost negligible unless it was pouring. we will definitely be back.

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$144

Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

“Nice alternatif for hotel” We were on the boat with only 2 people, so plenty of place ! We liked the marina and the boat very well. Something completely different than an hotelroom ... We had perfect weather so we used the different terraces on the boat depending on the wind and sun. The only point what could be better is the quality of the bedding (sheets, blankets, towels...) For this price you expect some better quality. Anyway, when we wil go back to the us I certainly will search for something similar to stay on

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$178

Bay and Beach Beauty

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 8 minutes

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$344

2 Great Waterfront FL Keys Homes - 1 Low Price

Marathon house

4 bedrooms / 4 bathrooms / sleeps 12

“Excellent Stay!” We rented out both sides for the week and we couldn't have asked for a better location! Great fishing, lobstering, and diving. We took the boat out almost everyday right from the house. Just enough room for our 9 people plus 1 baby. I loved how the kitchen was fully stocked with any possible cooking thing we needed. Everything worked perfect and was up to date.

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$371

NEW LISTING! Waterfront home on canal with Tiki hut and amazing water views!

Little Torch Key house

2 bedrooms / 1 bathroom / sleeps 7

Responds fast! avg. 51 minutes

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$90

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

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$458

Keys Cove Home #4 Wave from it all

Marathon Shores house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 38 minutes

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$573

Beautiful Beachfront Home w/Heated Pool+45' Dock

Marathon house

3 bedrooms / 3 bathrooms / sleeps 10

“Beautiful Home and Beautiful Beach Across the Street” My family had a fabulous relaxing vacation. The house and amenities were great. We had a beautiful front porch to watch the morning sunrise and beautiful views of Sombrero Beach. The guys enjoyed fishing everyday while the ladies enjoyed the beach. The beach opens at sunrise and closes at sunset. We had great weather and can't wait to return!

Responds fast! avg. 25 minutes

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$572

NEW LISTING! Oceanfront home with private hot tub and amazing ocean views!

Conch Key house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 49 minutes

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$176

Brand New 3 Story Key Largo Home

Key Largo house

5 bedrooms / 3 bathrooms / sleeps 16

Responds fast! avg. 2 hours 28 minutes

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Price per night from

$407

Bay Harbour D-114

Long Key house

3 bedrooms / 3 bathrooms / sleeps 8

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$328

76004 Overseas Highway

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

“Wonderful accommodations” Aside from being rainy for the majority of our stay, the accommodations were amazing. We will certainly be going back to this house. This house sleeps 8-10 adults comfortably. Freewheeler Realty was a pleasure to do business with and was the only company that was responsive to my inquiries. The house has an amazing view, full laundry, kitchen upstairs and downstairs. My favorite part were the stairs that go directly into crystal clear water to snorkel!

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$328

Casa Havana

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

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$783

Waterfront condo with rooftop patio, balcony, and dock!

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 49 minutes

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Price per night from

$223

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

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$430

Million $$ Pool Home

Key Colony Beach house

3 bedrooms / 3 bathrooms / sleeps 8

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$440

The Water's Edge

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

“Perfect for a Memorable Key West Experience!” My family and I absolutely loved staying in this beautiful Key West home. Located in Truman Annex (a quiet, private community in Old Town Key West), the location is perfect for whatever you wish to do during your Key West experience. Ocean Paradise has gorgeous views from the 3rd level balcony, a wonderful screened-in porch on the main level (perfect for al fresco dining), and an incredible pool area with a larger than expected private pool and stunning landscaping that provides both shade and privacy. The home's interior is both spacious and functional, including lovely furnishings and everything you need for a memorable vacation in beautiful Key West. Just as important to us was the ease in managing our visit to Ocean Paradise. The owner and his staff were absolutely incredible to work with throughout the entire rental process. We had originally scheduled our visit for the 2014 Thanksgiving holiday week. However, a need arose which required us to cancel that planned stay. The property owner was gracious enough to work with us in our desire to reschedule our visit for May 2015, demonstrating a focus on and respect for his guests throughout the entire process. Our Key West vacation, and specifically our week-long stay in Ocean Paradise, was undoubtedly a memorable experience for me, my husband and our two adult children (as well as the little "furry" member of our family who also joined us for our Key West adventure). We will be returning to Key West, and when we do, Ocean Paradise will be our chosen "home away from home" during our stay!

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$843

Incredible Luxury Home with Waterfront!! Paradise

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 38 minutes

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Price per night from

$1,390

Catch of the Day!

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

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$110

Keys Cove Home #3 Bikini Bottom

Marathon Shores house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 38 minutes

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Price per night from

$573

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