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 77 rentals matching your search criteria
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Flagler Station

Type

  • Home
3 Bedrooms
2 Baths
6 Guests
With family in mind this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor space and pool to spend your days enjoying.

A Siesta Bay

Type

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

Southard Square Hideaway

Type

  • Condo
1 Bedroom
1 Bath
4 Guests
A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.

Brisa Del Mar

Type

  • Condo
2 Bedrooms
2 Baths
6 Guests
Sunrise, sunbathe, sunset, repeat! Enjoy spectacular ocean views from this lovely rental!

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.

Tropical Casita

Type

  • Home
1 Bedroom
2 Baths
2 Guests
If privacy is what you desire this is the property for you. Completely set back from street and fenced for you to enjoy your private pool and large outdoor space.

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!

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.

Bye Bye Birdie

Type

  • Townhouse
3 Bedrooms
2 Baths
6 Guests
Find serenity in this pleasant and spacious home with tons of Key West charm. Located in the Key West Golf Club, Bye-Bye-Birdie is a two-story townhome with three bedrooms and two bathrooms.

Coral Garden

Type

  • Townhouse
2 Bedrooms
2.5 Baths
4 Guests
For those looking for a cozy little getaway on a budget - Coral Garden is the asnwer!

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.

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