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 80 rentals matching your search criteria
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Osprey

Type

  • Cottage
0.5 Bedrooms
1 Bath
2 Guests
Great location, great price! Osprey is the perfect getaway rental for a couple who wants to enjoy everything Key West has to offer!

Conch Wind

Type

  • Townhouse
2 Bedrooms
2 Baths
4 Guests
CONCH WIND - Stop searching, Conch Wind is the rental home in Key West you have been hunting for!

Emma's Escape

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.

Alluring Porches

Type

  • Townhouse
3 Bedrooms
3 Baths
6 Guests
Feel the tropical allure of this spacious home in the center-of-it-all community of the historic Truman Annex!

A Little Slice Of Paradise

Type

  • Townhouse
2 Bedrooms
1.5 Baths
6 Guests
Located on the main road meandering through the secluded gated Key West Golf Club community, you’ll find A Little Slice of Paradise. Spend a month (or two) in this charming townhouse and you may never return home.

Verandah

Type

  • Home
2 Bedrooms
2.5 Baths
4 Guests
A beautifully designed yet comfortable private home that you may never want to leave, only to go outside to your private pool and secluded space to hang out - that's the Verandah!

Bayview Harbor

Type

  • Condo
2 Bedrooms
1 Bath
5 Guests
Looking for a peaceful retreat yet close to everything? Ideally located on Southard Street, within walking distance to the beach at Fort Zachary Taylor State Park, Duval Street and Mallory Square, Bayview Harbor is the spot you’ve been looking for.

Coral Breeze

Type

  • Townhouse
2 Bedrooms
1.5 Baths
4 Guests
For the golfer in the family and for those who just want an idyllic vacation spot, Coral Breeze is the logical choice!

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 contemporary condo at Truman Annex might just be the one.

Conch Adventure

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Nestled in a quiet corner of the Shipyard section in the desirable Truman Annex, this 2-bedroom 1 bath downstairs condo offers peace, quiet and convenience.

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