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 46 rentals matching your search criteria
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Southard Square Hideaway

Type

  • Condominium
Old Town
1 Bedroom
1 Bath
4 Guests

A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.

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.

Ibis

Type

  • Cottage
Old Town
1 Bedroom
1 Bath
2 Guests

Enjoy your private front porch in this quiet neighborhood in Old Town Key West. Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home with a shared pool on property.

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.

Wind Swept

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
6 Guests

Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States. All that and much more awaits you at Windswept!

Linger Longer

Type

  • Townhouse
Old Town
2 Bedrooms
1.5 Baths
5 Guests

Just imagine stepping out of the rental and stepping right into the pool!

Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath, 2-story town home, located in the President's Walk of Truman Annex.

The Dolphin House

Type

  • House
Old Town
4 Bedrooms
3.5 Baths
8 Guests

Twice the comfort, twice the amenities, that’s The Dolphin House, located in the exclusive Truman Annex community in the heart of Old Town.

Sundown Refuge

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!

Papaya Place

Type

  • Condominium
Ocean Side
2 Bedrooms
2 Baths
6 Guests

This great 2 bedroom, 2 bathroom, Key West condo located at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view overlooking the nature preserve.

Coral Breeze

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
4 Guests

For the golfer in the family and for those who just want an idyllic vacation spot, Coral Breeze is the perfect choice!

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.

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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