Vacation Rentals & House Rentals in Key West

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84 house rentals

BREATHTAKING Ocean views await at Tropical Daze

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Couldn't be better!!!” If you are looking to rest and relax, look no further.

Responds fast! avg. 2 hours 17 minutes

Match: Boat available Climbing frame

All filters match

Price per night from

$285

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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

1 of 2 match: Boat available, Climbing frame

1 of 2 filters match

Price per night from

$544

Luxury Vacation Rental Oceanfront in Key Largo, nr, Islamorada, Florida Keys

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Great place to stay” We stayed at Sally and andrew´s place for a week. When we looked for a place to stay, we wanted a place not to far of Key West and Miami, and this place was just great! There were lots of places to eat out, things to see, and Key West and Miami was not to far away. The apartment was great, Andrew was too! Everthing regarding the stay were done in a professionel way. Both before the stay and after. The way of paying could have been easier though, but that is not a big problem We had a great time, all four of us visiting from Norway. If anyone should ask me where to stay in that erea, I have absolutely no problem telling them about Sally and andrew´s place! Ps: Make shure to have the time to eat at Mrs Mac´s Kitchen...

1 of 2 match: Boat available, Climbing frame

1 of 2 filters match

Price per night from

$206

Waterfront Condo with Boat

Key Largo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$442

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: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$430

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: Climbing frame, 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: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$144

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$458

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$859

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Climbing frame, 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 12 minutes

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$458

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$401

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Climbing frame, 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 12 minutes

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$1,432

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Climbing frame, 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 12 minutes

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$1,432

The Caribbean Resort - Hemingway House North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Climbing frame, 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 12 minutes

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$1,088

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$630

“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: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$316

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: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$402

Beautiful Home on the Water

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, 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: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$402

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: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$574

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$562

“Beautiful property” This place is way nicer then the pictures. The property itself is breathtaking and its right on the water with a beautiful deck. I love that we had access to kayaks whenever we wanted. No one else but our party was there. The house seemed pretty clean but I wish it had a quick sweep again before we got there. The barstools had lots of dead flies. Which is weird because we didn’t have any flies around even while cooking outside. I loved that we could fish right off the deck. Just wished there was a pipe outside to wash up before going in. It’s definitely heaven, I woke up at 6 one day and enjoyed the sunrise n watching Dolfins and manitees. I would definitely stay here again.

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$316

Key Largo Rental Fantastic Views

Key Largo condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 20 minutes

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$402

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

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$459

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: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$402

Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$689

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$1,949

Responds fast! avg. 3 hours 34 minutes

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$1,606

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$4,015

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$263

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$700

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