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 51 rentals matching your search criteria
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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!

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!

Emma's Escape

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.

Southard Getaway

Type

  • Condominium
Old Town
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. Imagine arriving in Key West to this beach-like home within walking distance of all that Key West has to offer.

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.

Finn Key

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Recently remodeled, tastefully decorated. This rental is hard to beat!

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.

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.

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.

Key West Found

Type

  • Townhouse
Old Town
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!

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.

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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