The ultimate escape: Key West cottages with private pools

Picture this: After a late night out on Duval Street, you emerge from your Key West cottage to a private pool surrounded by lush foliage. The water gleams in the Florida sunshine as you recline. Time to enjoy your oasis.

Here are some Key West cottages with private pools we’re drooling over right now.

chairs by the pool at a key west vacation rental
a cozy living room in a key west cottage

Helen’s Hideaway

This Key West cottage has a heated pool great for a small family, and plenty of poolside loungers for sunbathing. Throw a few filets or veggie kabobs on the grill for a meal on the covered patio. Take a break from the outdoors in the light-filled living area with pool views.

Tour Helen’s Hideaway.

water fountains flowing into a pool
an outdoor dining area at a home in key west

Bahama House

With its pretty tile work and soothing waterfall, this retreat is reminiscent of a getaway in the Bahamas (hence the name!). Serve margaritas and fun bites on the Tommy Bahama–esque patio furnishings, and linger on the loungers under swaying palm fronds.

Tour Bahama House.

Passover Cottage

Located right in the heart of Key West, this tropical sanctuary comes with a private swimming pool and a deck surrounded by lush greenery. The tastefully appointed interior includes charming wood ceilings as well as updated bathrooms.

Tour Passover Cottage.

a private pool at a key west vacation home
rocking chairs on the deck on a florida cottage

Aqua Pearl Crest

This two-story vacation home has plenty of spots to enjoy the pool: around the edge on the cozy wicker furnishings, or on either of the porches, complete with ceiling fans.

Tour Aqua Pearl Crest.

a luscious backyard with a wading pool
the exterior view of a key west cottage

Fishtail Hideaway

If you and your sweetheart are searching for a romantic retreat, look no further than this darling cottage. The verdant gardens and uniquely private pool with fountain features will make you feel like you’ve stepped into Highgarden from Game of Thrones.

Tour Fishtail Hideaway.

Fishtail Hideaway - Key West, FL
a hot tub and hammock in the backyard of a key west home

Coconut Palm

This Key West cottage is just right for slowing down. The pool has a nice bench for simply wallowing. Afterwards, get cozy in the small hot tub, or take a nap on the hammock while enjoying the sea breeze.

Tour Coconut Palm.

Browse more vacation homes in Key West