Vacation Rentals & House Rentals in Florida Keys

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141 house rentals

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Diving, Fishing, Snorkeling, Kayaking Paradise

Key Largo townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 20 minutes

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$402

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$804

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$114

Waterfront Home In Florida Keys

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect Holiday in Tavernier” We had a wonderful time at Dan and Penny's home. They were very accommodating! The home is absolutely pristine and in a nice neighborhood. There wasn't a day that we did not see manatee and tarpon in the canal in front of the house. Perfect location for restaurants, shopping and activities either by land or water. Beautiful home with everything you need for a perfect vacation in the Keys!

Responds fast! avg. 1 hour 17 minutes

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$210

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Price per night from

$247

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$622

“Fantasic wedding on paradise!!” We picked Shadow Point because of it's fabulous secluded view and beautiful gardens on 2.5 acres. The house and cottage held up to 16 of us and was wonderfully decorated with period antiques. Our guests loved playing at their beach and kayaking and swimming around Key LargoSound. Our wedding was perfect with the full moon rising over our reception. We danced the night away in paradise.

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$2,410

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$108

The Tree House Old Town 2 Bedroom MONTHLY Rental

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$134

SANCTUARY IN PARADISE

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“What Florida dreams are made of” Growing up in South Florida and the Keys but now moved farm away, I wanted to show my husband and young children the Florida I remembered as a child. This my friends was more than my dreams could have asked for! We were tremendously blessed to have had the opportunity to share this paradise! Private, gated estate with coral wooded hammocks to stroll through, palm trees clicking in the breeze, flocks of ibis that grazed through the lush green yard that ended at the private water front. Orchids blooming in the trees welcomed us to the hammocks where we had our morning coffee to stunning colored sunrises. It had everything: super clean Keys styled house with a cute kitchen (that saved us on meal expenses), bedrooms and bathrooms that were perfect size and accommodations, and wifi. It was quiet yet welcoming to my kids. We kayaked and swam on Christmas morning! The hosts were gracious and really made us feel as we were family. It was a Christmas we will always cherish. "Give and it will be given to you. A good measure, pressed down, shaken together and running over, will be poured into your lap." Luke 6:38 Truly, after giving us the chance to come share your slice of heaven, our cup runneth over.

Responds fast! avg. 2 hours 42 minutes

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$984

Kokomo Cove Boat House

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“Boat ramp and beautiful pool in the heart of the Keys” We wanted a house on a canal in the Marathon area, where we have been vacationing for years. This house had its own boat ramp, so we rented kayaks for a week and launched effortlessly right on site. The pool is lovely and relaxing. The house is well equipped and centrally located so trips up to Key Largo and down to Key West are quick.

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$401

Royal Palm House

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Beautiful Home in Marathon” We truly loved this place, the home was clean, spacious and very comfortable! My husband still claims to this day that was the best sleep he has had in years and that's a big compliment coming from him! We loved having water access (although we didn't have a boat) it really made for some beautiful sunsets and sunrises! We found a couple of amazing restaurants that we visited on several occasions, the first and our favorite was Tarpon Creek following as a very close second was The Sunset Grill and Raw Bar, also our favorite breakfast spot became Juice Paradise Cuban Cafe (the best coffee). I'm only just now getting around to reviewing this place because we are planning another trip to the Keys in December and I was checking this place out and i didn't see our review and ask my husband about it (I thought he posted it and he thought I posted it), so finally 2 yrs later I'm giving our review!!! Unfortunately I see it's booked for our time frame and we are very disappointed about that but I know whoever booked it WILL NOT be disappointed! Thanks so much for an amazing experience, Gina & Scott PS we actually stayed Sept 2014 but it would only let me go back to Oct 2014! :-)

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$215

“Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated the commodious kitchen with a two-tier dishwasher and side-by-side refrigerator with ice/water dispenser. Having a washer and dryer on the premises was very helpful, since guests are requested to wash linens and towels before departing. Some drawbacks: the house did not come equipped with adequate staples, such as paper products, laundry detergent, and garbage bags, so be prepared to purchase these. There are no beaches or stores within walking distance. On a couple of nights, noisy neighbors talking on the street woke us up. (In general, though, the area is quiet.)

Responds fast! avg. 1 hour 0 minutes

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$672

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$501

Key Largo Rental Fantastic Views

Key Largo condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 20 minutes

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$402

Key Largo Ocean Front Villa with Dock and Incredible views

Key Largo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 20 minutes

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$459

Sunrise Waterfront Home

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$488

Bay Pointe

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$204

Breeze Swept

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$268

Blue Lagoon

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$318

Manatee Bay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$151

Island Time 1 (half of duplex)

Big Pine Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$141

Casa Turquesa

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$288

Island Time 2 (half of duplex)

Big Pine Key house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$148

Lafitte Landing

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$144

Pirate's Cove

Cudjoe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$118

Margarita Villa

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$189

Island Time (both halves of duplex)

Big Pine Key house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$236

Coral House

Ramrod Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$218

St. Croix

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$121

Villa Cayo

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$414

East Sister Rock Island

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$2,214

Seaside Condo 2 pools. sunny, quiet, near Old Town

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 48 minutes

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$107

Welcome to Paradise

Long Key townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$206

Villa Sombrero, Marathon

Marathon house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$656

Island Chalet

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$161

Cozy Couple Getaway! or Great Family Home

Key Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$144

Unique Houseboat on Dry Lot

Key Largo houseboat

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Quaint and unique rental” The houseboat was everything I expected and needed it to be. It slept our family of four comfortably - which was all we really needed. The weather was good so really the only thing we did at the houseboat was shower and sleep. We did also do a few loads of wash - having a full size washer and dryer was convenient. I bet if we spent more time there, we would have used the back yard, it is really neat and welcoming. Maggie was a gracious hostess and everything was exactly where and how she described it. All in all a great value.

1 of 2 match: Nightlife, Pets allowed

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Price per night from

$98

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