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Houses Florida Keys

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449 houses

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

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

PARADISE OCEAN FRONT HOME

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

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$326

FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 6 w/ 60 Feet of Dockage

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 6

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$285

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$310

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. 51 minutes

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$346

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

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$1,729

Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 1 hour 51 minutes

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$595

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 14 minutes

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$659

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

Paradise on the water

Key Largo house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 36 minutes

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$576

OUTSTANDING Oceanfront House with Pool and Deep water dockage!!

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

“Marathon house” A great house with an awesome ocean view! The house was very clean and the kitchen was well stocked with all we needed. We especially looked the pool area and boat dock. It accommodated our 38 ft fishing boat we brought with no problems. I would highly recommend this rental

Responds fast! avg. 3 hours 11 minutes

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$700

Waterside Bay

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

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$194

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

Key Colony Beach Home

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 46 minutes

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$264

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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$247

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

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$430

Bay Harbour D-114

Long Key house

3 bedrooms / 3 bathrooms / sleeps 8

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$328

132 Columbus Drive

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

“Fantastic getaway” This is a great vacation rental property for a couple or small groups of 4 or less people. First of all, you can't beat the panoramic view of the water and what's more, the water is just 10 ft away. The front yard is one of the best if not the best with a lot of gardening and the antiques placed in the garden easily beats the boring gnomes. The interior of the house has a very wood cabin like feel to it and if you're looking for modern furniture, you'll be disappointed but if you're into a quaint little cottage like atmosphere, this will not disappoint. The 2 bedrooms are well kept and there are tons of pictures on the wall from the owners' travels all over the world and they're very interesting. There is no flat screen TV but the old color TV is more than sufficient - it has cable with most big channels you'll need (no premium ones except maybe Encore). They also have a ton of Dvds and Music CDs for your entertainment if you ever get bored of the views from the wrap around deck :-) The sunrises from this deck are awesome if you can wake up early - no sunsets cuz that's on the other side but you can always walk/drive over to the Overseas highway within minutes to catch the sunsets from there. The other amenities worth mentioning are the inground hot tub/spa they have which was awesome - you can view the ocean from the spa. If that wasn't close enough a view, you can pick up the huge Kayak they have and walk right into the water and row away. If there was any drawback, it was these bugs called no-see-ums that come out in full force in the evenings and if you aren't taking necessary protection, they will wreak havoc on your skins, but the owners/realtors can't do much about this. Just get some Off spray or something and you'll be fine. Overall this was a memorable trip for us and we hope it will be for you too. Thanks!

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$263

Bay and Beach Beauty

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 56 minutes

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$399

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

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$347

Home with Open Ocean,Spectacular Sunset views & Private Launch (28 day rentals)

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

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$165

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

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$542

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 3 hours 18 minutes

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$693

Oceanfront Oasis - Pinch me am I dreaming!!!

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 53 minutes

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$6,224

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

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$86

BEBA'S REEF HOUSE

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 4

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$158

Blue vacation home, water front, boat dock, heated private Pool.

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

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$555

Private Heated Pool, New Boat Dock and Ready Enjoyment!

Key Colony Beach house

2 bedrooms / 1 bathroom / sleeps 4

“Keys” This house was awesome!! My family really enjoyed staying here! We plan on booking this house for next year already. It has everything you need! And it is fully renovated all throughout! We are happy we were able to find this!!

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$264

Charming Elevated Waterfront Home

Big Pine Key house

1 bedroom / 1 bathroom / sleeps 4

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$161

ROCK HARBOR CLUB P-8

Key Largo house

2 bedrooms / 2 bathrooms / sleeps 6

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$103

Catch of the Day!

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

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$119

Paridise Found

Tavernier house

3 bedrooms / 3 bathrooms / sleeps 13

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$776

Florida Keys Splendor at Hammer Point

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 4

“Winter Paradise!” My wife and I stayed at this great place in January 2014 and it was wonderful. It was very clean and well maintained. The canal was great to watch the fish jump and we saw Manatees almost every day. We especially liked the kayak and did a lot of site seeing from the ocean side. Migdy was great to work with and very accommodating. We would highly recommend this place to anyone.

Responds fast! avg. 3 hours 37 minutes

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$132

82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / sleeps 10

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$982

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 20

“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Responds fast! avg. 1 hour 29 minutes

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$2,138

Futura Yacht Club # 205

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

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$161

Relax Away- SOMBRERO BEACH- NEW 4BDRM W/ 40FT DOCK & POOL

Grassy Key house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$571

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