The ultimate escape: Key West cottages with private pools

A private pool at a Key West cottage rental
mother-in-law cottage of key west vacation rental

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.

Margaret Street Retreat

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.

water fountains flowing into a pool

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.

Outdoor pool in a backyard of a vacation home in Key West, FL.

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.

large two story vacation home with outdoor pool in Key West, Florida

Villa of the Setting Sun

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.

Long and straight outdoor pool in the backyard of a vacation rental in Key West, FL.

Petronia Paradise

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 will make you feel like you’ve stepped into a tropical fairytale.

Rectangular outdoor pool in the backyard of a vacation rental in Key West, FL.

Sapodilla Villa

This Key West cottage is just right for slowing down. The shaded pool is just off a unique and lush patio area. Cool down in the pool and then unwind with friends and family on the nearby deck.

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