Vacation Rentals & House Rentals in Florida Keys

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197 house rentals

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Children's pool Freezer

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Price per night from

$344

Key Largo Bliss: Sun, Splash, Pickleball!

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Children's pool Freezer

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Price per night from

$567

Paradise at Moon Bay!

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Children's pool Freezer

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Price per night from

$229

Sunset Water Views! Moon Bay Key Largo Remodeled Condo with Boat Slip!

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children's pool Freezer

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Price per night from

$315

Tropical Island Getaway-Keys

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children's pool Freezer

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Price per night from

$338

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BEAUTIFUL YATCH IN THE KEYS ONCE IN A LIFETIME EXPERIENCE

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Freezer, Children's pool

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Price per night from

$252

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Freezer, Children's pool

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Price per night from

$158

Southernmost Beauty

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Children's pool, Freezer

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Price per night from

$267

Harbour Dream~3/2..DKKB24~McGinnis

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 17 minutes

1 of 2 match: Children's pool, Freezer

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Price per night from

$674

Buccaneer Boathouse

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Freezer

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Price per night from

$140

One-bedroom time share suite in the heart of Old Key West

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 26 minutes

1 of 2 match: Children's pool, Freezer

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Price per night from

$338

Grouper Therapy

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Freezer

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Price per night from

$213

Pelican Perch

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Freezer

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Price per night from

$183

Coconuts on the Water

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Children's pool, Freezer

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Price per night from

$205

Cabanas Key Largo Unit 6

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Pleasant place to stay for a few days” We got off on a bad foot as the room had not been cleaned before our arrival at 4:30PM (we were told we could check in a 3PM). The management was very responsive however, and paid for a complementary dinner at a fun, nearby restaurant by way of apology. The room was well designed and comfortable, if not spacious; the kitchenette and living/bedroom are all in one layout. It was fine for 2 guests but there would be no privacy if there were more. The cabana is right on the canals; boats pass frequently but it's not noisy. This was our first visit to the Florida Keys, and this cabana was a comfortable base for seeing Key Largo. It's not as convenient if you want to go as far south as Key West.

Responds fast! avg. 2 hours 15 minutes

1 of 2 match: Children's pool, Freezer

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Price per night from

$172

Historic Carriage House

Key West cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Children's pool, Freezer

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Price per night from

$229

Clean Apartment in Old Town Key West (Best Downtown Locations)

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 52 minutes

1 of 2 match: Children's pool, Freezer

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Price per night from

$384

Clean Apartment in Old Town Key West (Best Downtown Locations)

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 52 minutes

1 of 2 match: Children's pool, Freezer

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Price per night from

$384

American Shoal Lighthouse Suite Duval St. and Pool

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Freezer

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Price per night from

$430

Key West Suites Hotel unit 201

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Freezer

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Price per night from

$1,145

Motel Room #1, Private Entrance, Beach and Marina

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 37 minutes

1 of 2 match: Children's pool, Freezer

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Price per night from

$212

Responds fast! avg. 1 hour 37 minutes

1 of 2 match: Children's pool, Freezer

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Price per night from

$315

Bayside Condo, marina, pool and beach

Islamorada condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Phenomenal keys experience!” This bay front condo is the perfect destination for the entire family! The fishing ranks up with the best in the world, there are plenty of other activities, and Key West is just a short trip down the beautiful HWY 1. I've had the pleasure of staying at this condo several times and have honestly never had a bad time (even during a cat 5 Trop Storm). There is too much to do, the condo is comfy, and the weather is always beautiful. Definitely recommend this condo!

1 of 2 match: Children's pool, Freezer

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Price per night from

$253

Reef Resort - Peaceful Getaway 204

Marathon condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“A lovely condo” The condo was nicely appointed and was a great mid location to explore the Florida Keys. The pool was large & refreshing. There were bikes, kayaks & paddle boats to use. We met a few residents who were very friendly. A very nice condo!

1 of 2 match: Children's pool, Freezer

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Price per night from

$352

Responds fast! avg. 1 hour 37 minutes

1 of 2 match: Children's pool, Freezer

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Price per night from

$281

1 Bedroom, Full Kitchen, Mini Split Air, Beach and Marina Apt #1

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 37 minutes

1 of 2 match: Children's pool, Freezer

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Price per night from

$281

Shipyard-1/2 Block Duval Street

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Children's pool, Freezer

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Price per night from

$229

Ocean Vista

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Children's pool, Freezer

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Price per night from

$201

Nature's Boutique

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Children's pool, Freezer

1 of 2 filters match

Price per night from

$229

Salty Retreat

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Freezer

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Price per night from

$447

1 of 2 match: Children's pool, Freezer

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Price per night from

$573

Responds fast! avg. 1 hour 37 minutes

1 of 2 match: Children's pool, Freezer

1 of 2 filters match

Price per night from

$281

Beautiful Home on the Water

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Freezer

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Price per night from

$327

Keys Life

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Freezer

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Price per night from

$233

Sailfish Manor

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Children's pool, Freezer

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Price per night from

$383

Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Children's pool, Freezer

1 of 2 filters match

Price per night from

$344

Rent a Piece of Paradise in Key Largo

Key Largo caravan/mobile home

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Freezer

1 of 2 filters match

Price per night from

$228

Oceanfront Condo w/Lake, Kayaks, Paddleboards & Bikes

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Freezer

1 of 2 filters match

Price per night from

$447

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