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!

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Displaying 49 - 60 of 76 rentals matching your search criteria
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Osprey

Type

  • Cottage
Old Town
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!

Pets Not AllowedPoolGated Community
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Bye Bye Birdie

Type

  • Townhouse
Stock Island
3 Bedrooms
2 Baths
6 Guests

Find serenity in this pleasant and spacious home with tons of Key West charm. Featuring an abundance of back yard space for lounging or entertaining, you will not want to leave this lovely retreat.

Pets Not AllowedWasher/DryerGrillPoolGated Community
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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.

Pets Not AllowedWasher/DryerPoolGated Community
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Boat House

Type

  • Cottage
Old Town
1 Bedroom
2 Baths
2 Guests

Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West.

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Key West Found

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

Just steps away from Harry Truman's "Little White House" you’ll find your vacation dreams come true!

Pets Not AllowedWasher/DryerPoolGated Community
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Cottage by the Pool

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
4 Guests

In this cozy home you will find yourself nestled in the center of the Key West Golf Club on a secluded lane that cuts through the heart of its community.

Pets Not AllowedWasher/DryerGrillPoolGated Community
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Treetop Paradise

Type

  • Condominium
Old Town
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.

Pets AllowedWasher/DryerGrillPoolGated Community
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Duval Breeze

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches!

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Coral Garden

Type

  • Townhouse
Stock Island
2 Bedrooms
2.5 Baths
4 Guests

For those looking for a cozy little getaway on a budget - Coral Garden is the asnwer!

Pets Not AllowedWasher/DryerGrillPoolGated Community
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Artist Garden

Type

  • House
Old Town
2 Bedrooms
2.5 Baths
4 Guests

This spacious home with a large outside deck is tucked away on a quiet lane in the Truman Annex, yet only a short walk to all attractions.

Pets Not AllowedWasher/DryerGrillPoolGated Community
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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.

Pets Not AllowedWasher/DryerPoolGated Community
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