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!

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Displaying 61 - 71 of 71 rentals matching your search criteria
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Key West Charming

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.

Pets Not AllowedWasher/DryerPoolGated Community
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Tranquility

Type

  • Cottage
Old Town
1 Bedroom
1.5 Baths
4 Guests

Settled in a small community in Old Town, only a short walk to Duval Street, this lovely cottage offers everything you can expect from a perfect Key West rental.

Pets Not AllowedGrillPoolGated Community
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Casa de Rosalie

Type

  • House
Old Town
3 Bedrooms
2 Baths
8 Guests

Built in 1889 with original Dade County Pine, history comes alive when you enter this luxurious private home.

Pets AllowedWasher/DryerGrillPoolMonthly Rental
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Paradise Place

Type

  • Condominium
Old Town
1 Bedroom
1 Bath
4 Guests

Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach.

Pets AllowedWasher/DryerGrillPool
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Coral Breeze

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
4 Guests

Coral Breeze is a two bedroom town home located in the gated community at the Key West Golf Club on Stock Island. This modern and comfortable home is perfect for a couple or small family looking to stay for a month in Key West.

Pets AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental
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A Place In Paradise

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!

Pets Not AllowedWasher/DryerPoolGated Community
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Paradise Palms

Type

  • House
Old Town
2 Bedrooms
2 Baths
6 Guests

Make your next Florida vacation something special with this charming home in a quiet, upscale enclave that is close to everything!

Pets Not AllowedWasher/DryerGrillMonthly Rental
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Brisa Del Mar

Type

  • Condominium
Ocean Side
2 Bedrooms
2 Baths
6 Guests

Enjoy spectacular ocean views from this lovely rental!

ElevatorHot TubPets Not AllowedWasher/DryerGrillPoolGated Community
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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.

Pets Not AllowedWasher/DryerGrillPoolGated Community
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Always Your Paradise

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.

Pets Not AllowedWasher/DryerGrillPoolGated Community
View Details

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