Key West Vacation Rentals

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Search nearly 100 Key West vacation rentals ranging from intimate 1 bedroom cottages to large 5 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 26 rentals matching your search criteria
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Parrot Perch

Type

  • Condominium
Old Town
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.

Shipyard Treasure

Type

  • Condominium
Old Town
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.

Key West Charming

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Key West Charming is just the perfect home away from home! There is no need to look any further for your dream come true vacation rental.

Bahamian Reed

Type

  • Townhouse
Old Town
2 Bedrooms
1.5 Baths
5 Guests

Look No Further!! Bahamian Reed is the vacation rental home for those special vacation memories that you will come back to again and again.

Sunset Celebration

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

This unit, aptly named Sunset Celebration, is close to Mallory Square, the perfect place to enjoy the local festivities that close the day every night.

Conch Adventure

Type

  • Condominium
Old Town
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.

Buena Vista

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

The historic brick foundry residence is in the luxurious gated community of the Truman Annex, appropriately named after President Harry Truman.

Easy Livin'

Type

  • House
Old Town
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.

A Siesta Bay

Type

  • Condominium
Old Town
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!

Finn Key

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Recently remodeled, tastefully decorated. This rental is hard to beat!

Beach House Condo

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.

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