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 1 - 12 of 80 rentals matching your search criteria
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Key West Casa

Type

  • Townhouse
3 Bedrooms
2 Baths
6 Guests
This spacious 3 bedroom apartment is located in Shipyard of Truman Annex, one of the most desirable Key West communities, close to Blue Heaven and Santiago's Bodega, one of Key West most popular restaurants.

Breezy Bungalow

Type

  • Townhouse
2 Bedrooms
2.5 Baths
4 Guests
Looking for a nice home in Truman Annex community? Breezy Bungalow is the answer for you!

Lighthouse Villa

Type

  • Home
3 Bedrooms
4.5 Baths
8 Guests
Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home.

Artist Garden

Type

  • Home
2 Bedrooms
2.5 Baths
6 Guests
This spacious home with a large outside deck is tucked away on a quiet lane of Truman Annex, yet only a short walk to all attractions.

Parrot Perch

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
Unbeatable location at a great price! The Parrot Perch is in the gated Shipyard Community of the prestigious Truman Annex.

A Barefoot Retreat

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Looking for the perfect home away from home? No need to look any further!

No shoes needed at “A Barefoot Retreat” in the lovely Shipyard section of the historic Truman Annex private community.

Poolside Paradise

Type

  • Home
2 Bedrooms
2 Baths
4 Guests
Spending time in the warm breezes of Key West – isn’t that why you come here? At Poolside Paradise you can enjoy outdoor living at its best!

Beach House Condo

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.

Nautical Dreams

Type

  • Cottage
2 Bedrooms
2 Baths
4 Guests
Nautical Dreams is the perfect spot for whatever you desire - parties or peace and quiet in a Key West vacation home.

La Casita

2 Bedrooms
1 Bath
4 Guests
The location of La Casita cannot be beat -- right in the heart of Old Town yet on a quiet lane, only steps to Duval Street.

Treetop Paradise

2 Bedrooms
2 Baths
4 Guests
Located in the historic Bahama Village neighborhood, nestled amongst the palms, you‘ll find the stately building that houses Treetop Paradise.

Sundown Refuge

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!

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