Vacation Rentals & House Rentals in Florida Keys

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Islamorada Waterfront Paradise Getaway!

Islamorada house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Wonderful Romantic Get-Away” We absolutely enjoyed our stay here and would recommend it to others. The owners were very friendly and pleasant, and the apartment was incredibly clean. The tiki hut over the private lagoon was amazing. We kept finding little things all over the apartment while we were there - drinks, books, games, etc. It was a totally wonderful time, and we want to go back!

Match: Bicycles available Staffed property

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Price per night from

$571

Luxury condo overlooking harbor with ocean view

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$389

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Price per night from

$907

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$907

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$471

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$284

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Price per night from

$262

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$510

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$525

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Bicycles available Staffed property

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Price per night from

$523

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Staffed property

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Price per night from

$970

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Staffed property

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Price per night from

$525

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$484

Coconut Mallory Resort and Marina

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$346

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Charming Elevated Waterfront Home

Big Pine Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Staffed property, Bicycles available

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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: Staffed property, Bicycles available

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Price per night from

$143

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: Staffed property, Bicycles available

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Price per night from

$337

Coconut Cay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Bicycles available

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Price per night from

$207

New Listing Family Friendly

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Bicycles available

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Price per night from

$367

Motel Room #2, 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: Bicycles available, Staffed property

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Price per night from

$211

Sleeping Room, Private Entrance and use of RV Park Bathrooms, Beach and Marina

Key Largo private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Bicycles available, Staffed property

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Price per night from

$144

Key Largo Oceanfront Condo with Dock and Spectacular views

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 23 minutes

1 of 2 match: Staffed property, Bicycles available

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Price per night from

$400

Gorgeous waterfront home

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Staffed property, Bicycles available

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Price per night from

$457

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: Staffed property, Bicycles available

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Price per night from

$351

Reef Resort Getaway 205

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Staffed property, Bicycles available

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Price per night from

$319

Family Friendly House In Paradise

Summerland Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Staffed property, Bicycles available

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Price per night from

$514

Salty Retreat

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Staffed property, Bicycles available

1 of 2 filters match

Price per night from

$446

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Staffed property, Bicycles available

1 of 2 filters match

Price per night from

$343

Oceanfront Condo w/Lake, Kayaks, Paddleboards & Bikes

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, 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: Staffed property, Bicycles available

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Price per night from

$251

Studio Blue

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Staffed property, Bicycles available

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Price per night from

$331

Spacious 1 Bedroom, Full Kitchen, Central Air, Beach, Marina and Docks

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“Tranquil and friendly” This was a place we found after months of searching and having another owner cancel out on us. We came in with a pre judgement of the place and BOY were we wrong. Everyone is super nice, everyone there(employees and guests) are very caring and friendly. The apartment was very comfy and well equipped, although anextra blanky or throw would have been nice to have for the sofa lounging. We are only 4 days into it but all is great!

Responds fast! avg. 1 hour 37 minutes

1 of 2 match: Bicycles available, Staffed property

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Price per night from

$280

Responds fast! avg. 1 hour 37 minutes

1 of 2 match: Bicycles available, Staffed property

1 of 2 filters match

Price per night from

$280

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: Bicycles available, Staffed property

1 of 2 filters match

Price per night from

$280

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: Bicycles available, Staffed property

1 of 2 filters match

Price per night from

$211

Responds fast! avg. 1 hour 37 minutes

1 of 2 match: Bicycles available, Staffed property

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Price per night from

$314

Responds fast! avg. 1 hour 37 minutes

1 of 2 match: Bicycles available, Staffed property

1 of 2 filters match

Price per night from

$280

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

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Bicycles available, Staffed property

1 of 2 filters match

Price per night from

$314

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rentals in Florida Keys

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