Key West Vacation Rentals

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Search nearly 100 Key West vacation rentals ranging from intimate 2 bedroom cottages to large 6 bedroom homes. With properties in popular Key West communities like Truman Annex, Key West Golf Club, and 1800 Atlantic plus a variety of pet friendly and monthly rentals, we are sure we have the perfect fit for your trip. Our local Key West team of vacation rental experts has been helping travelers plan amazing vacations for decades and loves to share their local knowledge. Don't hesitate to contact us with questions or for help finding the perfect rental and booking your Key West vacation!

Displaying 49 - 60 of 94 rentals matching your search criteria
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A Place In Paradise

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!

Nautical Dreams

Type

  • Cottage
2 Bedrooms
2 Baths
6 Guests
In a small gated community this perfect cottage with a large private deck to allow all the privacy you would need to grill, dine and lounge.

Boat House

1 Bedroom
2 Baths
2 Guests
This unique 1 bedroom, 2 bath cottage is about to become your home away from home!
Step in to a tranquil community on a quiet lane, only blocks to Duval Street and discover BOAT HOUSE!

Tranquility

Type

  • Cottage
1 Bedroom
1.5 Baths
4 Guests
Settled in a small community of Old Town yet only a short walk to Duval Street, this lovely cottage offers everything you can expect from a perfect Key West rental

Bayview Harbor

Type

  • Condo
2 Bedrooms
1 Bath
5 Guests
Enjoy your morning coffee, afternoon cocktail or freshly grilled fresh catch on the outside patio when taking a break from exploring Key West!

Lazy Gecko

Type

  • Condo
2 Bedrooms
1.5 Baths
4 Guests
Beautifully recently remodeled 2 bed/1.5 bath condo located just 4 blocks to Duval Street and the Historic Seaport.

Papaya Place

Type

  • Condo
2 Bedrooms
2 Baths
6 Guests
Atlantic Ocean is just at your reach when staying at Papaya Place! You can almost hear the waves of the ocean!

Emma's Secret

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Lush tropical outdoor setting within this small compound, privacy as you enjoy the pool and outdoor gardens.

Spa On Duval

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
This beautiful vacation rental is located in the heart of Old Town, close to everything Key West has to offer!

Shipyard Treasure

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Finding a perfect property for your family vacation is easier said than done, but this beautiful apartment might just be the one.

Contemporary Condo at Truman Annex - Walk to Beach/Duval Street

Finn Key

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Just steps away from the pool! Recently remodeled, tastefully decorated. This rental is hard to beat!

A Little Slice Of Paradise

Type

  • Townhouse
2 Bedrooms
1.5 Baths
6 Guests
Townhouse located just steps from the Key West Golf Course Club House and after a round of golf head over to either of the two pools to cool off.

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