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!

Displaying 49 - 60 of 78 rentals matching your search criteria
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Ibis

Type

  • Cottage
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.

Verandah

Type

  • Home
2 Bedrooms
2.5 Baths
4 Guests
A beautifully designed yet comfortable private home that you may never want to leave, only to go outside to your private pool and secluded space to hang out - that's the Verandah!

Papa's Cottage Retreat

Type

  • Cottage
1 Bedroom
1 Bath
2 Guests
As you step through the natural wooden gate onto the brick pathway, you will be embraced by this private garden oasis.

Flagler Station

Type

  • Home
3 Bedrooms
2 Baths
6 Guests
With family in mind this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor space and pool to spend your days enjoying.

Southard Getaway

Type

  • Condo
2 Bedrooms
1.5 Baths
5 Guests
“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree.

Emma's Secret

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Lush tropical outdoor setting within this small compound, privacy as you enjoy the pool and outdoor gardens.

Finn Key

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Just steps away from the pool! Recently remodeled, tastefully decorated. This rental is hard to beat!

Conch Republic Retreat

Type

  • Cottage
2 Bedrooms
2 Baths
4 Guests
Located in the quiet neighborhood of The Meadows, you’ll find the Conch Republic Retreat, a quintessential cigar maker’s shotgun style house, circa 1890.

Crowner's Jewel

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Imagine being able to walk to the Sunset Celebrations every single evening! Only couple blocks to Mallory Square you can find this true gem!

Truman's Hideaway

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
It’s hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. But either way, you can enjoy breathtaking sunsets with a glass of wine from your own private porch.

Parrot Perch

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
Unbeatable location at a great price! The Parrot Perch is in the gated Shipyard Community of the prestigious Truman Annex.

Key West Found

Type

  • Townhouse
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!

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