Vacation Rentals & House Rentals in Florida Keys

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266 house rentals

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East Sister Rock Island

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$2,218

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$248

Boaters’ Paradise - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$1,490

Family Friendly House In Paradise

Summerland Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$518

4 Bd w/Pool, Bayside - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$1,490

Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$317

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$259

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$2,012

Harbor Walk Hideaways

Key West b&b

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$1,306

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$502

Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 2 hours 26 minutes

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$604

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

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$460

Large Waterfront 4 balcony Key Largo Townhouse with Oceanfront Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 20 minutes

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$403

Lobster Lagoon

Stock Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$978

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$701

FALL IN LOVE with your home away from home!

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$207

Ocean Breeze Oasis With Excellent Boating Access

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$604

ISLAND DREAM

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$776

Key West House

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$690

Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.

Cudjoe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$518

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$914

These homes match some but not all of your filters. Clear all filters

Executive Bay Club- great unit, great location!,

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 20 minutes

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$206

Lovely 2 bedroom, 2 bath condo at La Brisa.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$161

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$379

Kawama Tower Unit 512

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$340

Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 56 minutes

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$494

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$167

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$822

Luxurious Oceanfront Condo

Tavernier apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$299

Blackbeard's Escape

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$360

Luxury 4-Bedroom Home with Resort Privileges

Tavernier villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$1,667

Island Suite @ KW Vacation

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$403

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$213

Beautiful condo with ocean view(distant)

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$259

The Mermaid House

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 2 minutes

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$343

Tranquil Oceanview Penthouse Paradise

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$374

Comfy Family Home in a Gorgeous Gated Community

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$344

BEAUTIFUL YATCH IN THE KEYS ONCE IN A LIFETIME EXPERIENCE

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$253

Viewing 38 of 266
rentals in Florida Keys

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