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

Helen’s Hideaway

cottage with pool and sun deck | Vacasa

key west cottage rental | Vacasa

This Key West cottage has a heated pool great for a small family, and plenty of poolside loungers for sunbathing. Throw a few fillets 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

bahama house in key west | vacasa

key west outdoor patio on sunny day | vacasa

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

vacasa key west vacaton rental with pool

key west cottage living room | vacasa

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 reading on the sofa or catching your favorite show.

Tour Caribbean Fling.

Villa Bougainvillea

pool and lawn chairs in key west | key west

key west oceanfront patio | vacasa

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

pool and deck in key west | vacasa

beautiful deck in key west florida | vacasa

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

green plants and fountain in key west | Vacasa

cute cottage in key west | Vacasa

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

pool at key west vacation rental | Vacasa

hot tub and hammock in key west | Vacasa

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.

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Author: Hannah Morrison

Hannah hails from Telluride, CO and currently lives in Portland, where she works as writer, editor, and unofficial resident poet for Team Vacasa. You'll often find Hannah singing and dancing down the sidewalk, making really tall sandwiches, and planning her next long run.