Vacation Rentals & House Rentals in Florida Keys

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156 house rentals

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NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Bicycles available Shared outdoor pool (unheated)

All filters match

Price per night from

$1,946

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

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 29 minutes

Match: Bicycles available Shared outdoor pool (unheated)

All filters match

Price per night from

$338

Match: Bicycles available Shared outdoor pool (unheated)

All filters match

Price per night from

$911

SEAPORT SUMMIT in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Bicycles available Shared outdoor pool (unheated)

All filters match

Price per night from

$911

3Bd/2Ba POOL on Canal, Dock, Kayaks, Bikes, Fishing Poles, Sombrero Beach 2.3mi

Marathon Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Bicycles available Shared outdoor pool (unheated)

All filters match

Price per night from

$573

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Bicycles available Shared outdoor pool (unheated)

All filters match

Price per night from

$344

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Shared outdoor pool (unheated)

All filters match

Price per night from

$431

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Shared outdoor pool (unheated)

All filters match

Price per night from

$286

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Shared outdoor pool (unheated)

All filters match

Price per night from

$366

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Shared outdoor pool (unheated)

All filters match

Price per night from

$525

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Bicycles available Shared outdoor pool (unheated)

All filters match

Price per night from

$525

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Shared outdoor pool (unheated)

All filters match

Price per night from

$525

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Shared outdoor pool (unheated)

All filters match

Price per night from

$471

Coconut Mallory Resort and Marina

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Shared outdoor pool (unheated)

All filters match

Price per night from

$523

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

Lovely 2 bedroom, 2 bath condo at La Brisa.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$161

Charming Elevated Waterfront Home

Big Pine Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$172

Cozy Couple Getaway! or Great Family Home

Key Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$144

Coconut Cay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$207

New Listing Family Friendly

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$367

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$212

Luxury 4-Bedroom Home with Resort Privileges

Tavernier villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,661

Island Suite @ KW Vacation

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$401

Beautiful condo with ocean view(distant)

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$258

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$363

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

  • Studio
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$286

BEAUTIFUL YATCH IN THE KEYS ONCE IN A LIFETIME EXPERIENCE

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$252

Key Largo Oceanfront Condo with Dock and Spectacular views

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 20 minutes

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$401

Gorgeous waterfront home

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$458

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: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$352

Reef Resort Getaway 205

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$320

Family Friendly House In Paradise

Summerland Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$516

Salty Retreat

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$447

Oceanfront Condo w/Lake, Kayaks, Paddleboards & Bikes

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$447

The Butterfly Cottage

Marathon house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$251

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$974

Studio Blue

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$331

WATERFRONT TOWNHOME IN ISLAMORADA K1

Islamorada apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$184

Waterfront luxury Villa (14) with sunset views and boat slip

Marathon condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$300

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