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 13 - 24 of 28 rentals matching your search criteria
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Serenity

Type

  • Cottage
Old Town
1 Bedroom
1 Bath
2 Guests

Located in Bahama Village, a quaint neighborhood in Old Town Key West, this beautifully renovated conch home is a romantic island getaway. This rental is a guest house situated in the back yard of a private residence.

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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.

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Key Lime Pie

Type

  • Cottage
Old Town
2 Bedrooms
2 Baths
4 Guests

Key Lime Pie is a private cottage that perfectly encompasses the “Key West vibe” that you’re looking for. The minute you walk in to see the bright, sunny walls and local artwork, you know you are somewhere special.

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Emma's Secret

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life.

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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.

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Tumi's Time Out

Type

  • Townhouse
Old Town
2 Bedrooms
2 Baths
4 Guests

Tumi’s Time Out is a 2-bedroom, 2-bathroom town-home in the sought after Windward Park community. A secluded compound that is a tropical hideaway, surrounded by lush palms and balmy breezes.

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Wind Swept

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
6 Guests

Situated in the gated community at the Key West Golf Club, Wind Swept is a perfect retreat for a small family or two couples looking for a monthly rental.

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Coral Garden

Type

  • Townhouse
Stock Island
2 Bedrooms
2.5 Baths
4 Guests

Coral Garden is a two bedroom town home in the quiet gated community of Coral Hammock located on Stock Island. Perfect for families or those who are working from home. Close to all that Key West has to offer.

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Coral Palm

Type

  • Townhouse
Stock Island
3 Bedrooms
3 Baths
6 Guests

Coral Palm is a lovely 3 bedroom, 3 bathroom, 2 story town home located in the private gated community of Coral Hammock on Stock Island.

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Perfect Pineapple

Type

  • House
Old Town
2 Bedrooms
1 Bath
4 Guests

Long considered a sign of hospitality, the pineapple is widely recognized as sign of Welcome and Friendship, and so we welcome YOU to the Perfect Pineapple!

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Bogey's Retreat

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
4 Guests

Welcome to your home away from home in Key West. This lovely town home is located in the Key West Golf Club Community, and allows you to enjoy all that Key West has to offer while staying in a relaxing environment.

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