Vacation Rentals & House Rentals in Key West

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51 house rentals

500 Ocean - Tropical Florida Keys Vacation Home

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Zen Oasis with a Dock” Loved 500 Ocean. Quiet, Local, Relaxed. Great location, Good fishing and amenities for the boat ( tons of dock space, bait freezer, fish cleaning station) You have to watch that canal though it's super shallow (as in barely 2 feet most of the way). Everything is the house was nice and comfortable. Coconut Chuck was super helpful with our stay and provided a lot of information ahead of time!

Responds fast! avg. 2 hours 56 minutes

Match: Boat available Swing set or jungle gym

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Price per night from

$326

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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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$573

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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$745

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: Swing set or jungle gym, 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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$487

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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$687

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: Swing set or jungle gym, 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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$745

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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$745

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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$630

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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$745

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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$1,145

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: Swing set or jungle gym, 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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$1,775

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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$916

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Swing set or jungle gym

1 of 2 filters match

Price per night from

$263

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Swing set or jungle gym

1 of 2 filters match

Price per night from

$158

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, Swing set or jungle gym

1 of 2 filters match

Price per night from

$601

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Swing set or jungle gym

1 of 2 filters match

Price per night from

$285

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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$174

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$458

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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$144

Beautiful Home on the Water

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$326

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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$572

Amazing Ocean View Condo on the Beach!

Marathon apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Our Spirits were renewed!” Things don't happen by chance! Little did we know six months ago when we booked our vacation how much we would really, really NEED a quiet and peaceful week! This little corner of Marathon is exactly that: quiet and peaceful. The condo is very comfortably furnished, very clean, and the view is - well, I don't think there is a 'better' view anywhere! It's picture perfect - even to the gorgeous green iguana on the palm tree! (but you have to look quick - they move fast!). We had our son, daughter in law and two little grandkids with us...it was perfect! Sunrise with coffee by the pool, under the Chickee or on the patio...awesome! Lots to do for families or singles very close by...yup...you really can even have pizza delivered if you don't want delicious, fresh seafood!..and wow! are there some awesome spots for that!! Communication with the owners is impeccable...could NOT be better. These are the folks with whom you love to do business!! Thanks so much, Todd and Jamie!

1 of 2 match: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$342

1 of 2 match: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$561

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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$687

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$1,943

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$4,003

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$697

Cozy Keys Cottage Islamorada FL.

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 10 minutes

1 of 2 match: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$407

1 of 2 match: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$262

“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: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$326

Boater's Paradise

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$377

Coconut Mallory Resort and Marina

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$523

Private Island Rental with 19' Boat, Seabird Key

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Heaven On Earth!” From the moment you step foot on this beautiful island paradise, you'll feel like you've been transported to your own little private world! Every amenity has been thought of from an outstanding outdoor kitchen, complete with state of the art grill, oven and microwave along with dinnerware, glassware etc. Not to mention the kitchen inside the house comes complete with all you need also. Even spices, just not food! The house itself is amazing and has a awesome stereo system so you can have music in the house, on the decks and on then beach! You can snorkel, swim, fish, sail, canoe, kayak, go tubing walk along the perfectely maintained tropical paths. From sunrise to sunset you day will be filled with beautiful scenerey, The view from the front porch is my favorite, I could sit there all day and have! This was our 7th trip and we had a extended stay of 10 glorious days, also our first trip with friends who loved it as much as we do! We've spent my birthday and our anniversary (back to back) here many of times and there is no place else we would rather be! The island is alive with hermit and land craps and Iguanna's and birds of all sorts. It's so funny to see a hermit crap go by with some sort of object he found as a shell. At night when you turn all the outside lights on it's like a magical transformantion! I can not say enough good things about Seabird Key. The owners and care takers do such a amazing job! Thank you for sharing this tropical paradise with us and we hope to be back again soon!

1 of 2 match: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$2,002

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$431

the private and secluded PENINSULARHOUSE

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Nice get away” Beautiful and relaxing. Did alot of snorkeling right off the deck. Enjoyed the paddle boats and the kayaks. When we make it down that way again I would definitely stay here.

1 of 2 match: Swing set or jungle gym, Boat available

1 of 2 filters match

Price per night from

$371

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