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 55 rentals matching your search criteria
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La Casita

Type

  • House
Old Town
2 Bedrooms
1 Bath
4 Guests

The location of La Casita cannot be beat -- right in the heart of Old Town yet on a quiet lane, only steps to Duval Street. This property is a monthly rental only. Sleeps 4 people.

Shipyard Treasure

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.

Bayview Harbor

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
5 Guests

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

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.

Land Of Love

Type

  • Townhouse
Old Town
2 Bedrooms
1.5 Baths
4 Guests

Your perfect escape to Key West awaits you in the Land of Love.

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.

Lavender Jungle

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.

First Breath

Type

  • House
Old Town
3 Bedrooms
2 Baths
6 Guests

Bring the family to this 3 bed, 2 bath private conch home and enjoy your large private pool and outdoor area as the days pass by.

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.

Windchime

Type

  • Condominium
Old Town
0.5 Bedrooms
1 Bath
2 Guests

Searching for an affordable monthly vacation rental in the heart of Key West? Do you plan on spending most of your time enjoying all that Key West has to offer and seeing what if feels like to really live like a local? Then tune into Windchime!

Conch Condo

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

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

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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