Vacation Rentals & House Rentals in Key West

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92 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

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Price per night from

$315

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The Caribbean Resort - Hemingway House North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$487

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 45 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 45 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$687

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$1,775

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$916

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$745

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$1,775

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

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$573

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$1,145

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

$107

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

$773

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

$515

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

$516

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

$430

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

$441

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 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

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$458

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

$229

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

$224

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

$337

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

$395

1 of 2 match: Boat available, Games room

1 of 2 filters match

Price per night from

$819

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: Games room, Boat available

1 of 2 filters match

Price per night from

$401

“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

$315

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

Diving, Fishing, Snorkeling, Kayaking Paradise

Key Largo townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 20 minutes

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$401

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

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$401

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

$573

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$561

“Perfect get-away cottage exceeded our expectations.” Just back from enjoying the cottage, Conched Out, at Caribbean Soul Charters on Conch Key. Awesome rustic cottage with tons of nautical character and a sailboat right out the back door. Great location near Marathon allowed us to easily day trip up to Key Largo and down to Key West. My family took the 23' Compact sailboat out 3 times during the week and the sailing was awesome. Our boat was in great shape and the motor operated flawlessly. One of the best family vacations we've ever enjoyed. We can't wait to come back. The owners, Barry and Tammy Jo, were very friendly and great sources of local information.

1 of 2 match: Games room, Boat available

1 of 2 filters match

Price per night from

$327

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