Vacation Rentals & House Rentals in Florida Keys

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93 house rentals

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

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Games room

All filters match

Price per night from

$314

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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: Boat available, Games room

1 of 2 filters match

Price per night from

$106

Welcome to Paradise

Long Key townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Boat available, Games room

1 of 2 filters match

Price per night from

$205

Conch House - Dock Your Boat

Little Torch Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

1 of 2 match: Boat available, Games room

1 of 2 filters match

Price per night from

$770

Paradise at Moon Bay!

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Boat available, Games room

1 of 2 filters match

Price per night from

$229

mojito breeze getaway, islamorada

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

1 of 2 match: Boat available, Games room

1 of 2 filters match

Price per night from

$513

Oasis Canal-Front Home: Pool, 30ft Dock, BBQ, and more!

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Games room

1 of 2 filters match

Price per night from

$514

Waterfront Condo with Boat

Key Largo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$440

BAYSIDE CONDO WITH BOAT

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Want to go back” We just got home from our vacation in this apartment. We loved it. Jay took great care of us and was quick to help with any problems or needs. We rented the boat with the apartment and loved being able to walk downstairs and get onto our boat and out fishing for the day. We enjoyed using the grill on the porch and being able to eat our dinner outside enjoying the weather and views. We will definately return again. Thanks for a great vacation Jay.

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$428

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$573

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$859

The Hideaway: Discover and Lose Yourself! Newly Decorated Canal Front Home, Dock

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$144

The Caribbean Resort - Hemingway House North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$630

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$463

Blue Fish Point: Tranquil, Luxurious Waterfront Oasis, Amazing Sunsets, Pool, Ti

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$174

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Bird of Paradise - One Bedroom One Bath

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$573

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$1,432

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$1,088

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$401

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$1,432

Islamorada Ocean Views! Pool, Wi-Fi, Balcony, Gym, Covered Parking

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 44 minutes

1 of 2 match: Boat available, Games room

1 of 2 filters match

Price per night from

$172

Buttonwood Bay Key Largo Waterfront Townhouse

Key Largo apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Games room

1 of 2 filters match

Price per night from

$223

Tropical Island Getaway-Keys

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Games room

1 of 2 filters match

Price per night from

$336

1 of 2 match: Boat available, Games room

1 of 2 filters match

Price per night from

$816

salty slumber get away

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Games room

1 of 2 filters match

Price per night from

$394

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: Games room, Boat available

1 of 2 filters match

Price per night from

$400

“Perfect” Great house. Very clean and simple. You share the beach and dock with the two other houses in the property but was never an issue. Location is great in Largo. Martha was a great host and very friendly. Will definetly be going back.

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$314

Beautiful Home on the Water

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$327

Large Waterfront 4 balcony Key Largo Townhouse with Oceanfront Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 23 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$400

Diving, Fishing, Snorkeling, Kayaking Paradise

Key Largo townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 23 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$400

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!

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$571

“Fantastic Stay!” My husband and two sons (21 & 24) stayed in this condo over Christmas. This was our first stay in Key West and we wanted to be close to everything, but yet not right on Duval St. This location was perfect; literally a stones throw away from Duval St. The unit inside was decorated very lovely and had all the amenities one would need. I found the owners were nice to do business with, especially Deb who I mostly communicated with. My family and I enjoyed our stay in Key West immensely, we had so much fun! We met many very friendly people out and about town. We would love to visit again, if we do, we would like to stay in this condo or the Bella Vita, the owner's other condo.

Responds fast! avg. 14 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$286

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