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 seven Key West cottages with private pools we’re drooling over right now.

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.

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.

Caribbean Fling

If you’re looking for something a bit more intimate, this cabana-style cottage has a perfect swimming hole, lined with rich greenery. The open outdoor walkway between the living room and the kitchen allows for a pleasant cross breeze while you read on the sofa or catch your favorite show.

Tour Caribbean Fling.

Villa Bougainvillea

A private pool meets beautiful water views at this waterfront Key West cottage. The pool is nice and shaded, as is the outdoor bar! Blend up a smoothie before stretching out on a lounger overlooking the water, and keep a bowl of chips ready for hungry swimmers.

Tour Villa Bougainvillea.

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.

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.

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.

Can’t find what you’re looking for? Check out our other Key West vacation rentals.