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 30 rentals matching your search criteria
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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!

Parrot Perch

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
Unbeatable location! Only a block to famous Green Parrot bar yet in a secluded, quiet community of Truman Annex

Easy Livin'

Type

  • Home
3 Bedrooms
4 Baths
8 Guests
Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home.

The name says it all!

Beach House Condo

Type

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

Southard Getaway

Type

  • Condo
2 Bedrooms
1.5 Baths
5 Guests
Amazingly Perfect!!! That is how one of our guests reviewed Southard Getaway! This amazingly perfect rental can be yours as well!

Siesta Bay

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Here is your perfect opportunity to enjoy your stay in one of the most popular complexes of Key West, Truman Annex!

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.

Alluring Porches

Type

  • Townhouse
3 Bedrooms
3 Baths
6 Guests
Beautifully decorated and spacious home in the community of Truman Annex is awaiting for you!

Sundown Refuge

Type

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

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!

Step into this fantastic condo and the first thing you'll want to do is take off your shoes; feels just like home.

City Cay

Type

  • Condo
1 Bedroom
1 Bath
2 Guests
Recently renovated, modern and cozy upstairs apartment with a large balcony overlooking the neighborhood

Captains Wheel

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Beautiful 2 bedroom, 2.5 bath vacation rental. Enjoy the convenient proximity to most events Key West has to offer!

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