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

Imagine this: After a lively night on Duval Street, you step out of your cozy Key West cottage into your own private paradise. Sunlight dances on the pool, tropical foliage sways in the breeze, and your lounge chair is calling. Welcome to your personal oasis.

Here are a few Key West cottages with private pools we’re currently obsessed with.

private outdoor pool of vacation home in key west

Key to Paradise

3 bed | 3 bath | Dogs okay

Charming Key West home with a private pool, BBQ, and modern amenities just steps from the water. Enjoy outdoor living, a fully equipped kitchen, and easy access to water activities, shops, and dining. Ideal for families or adventure seekers.

water fountains flowing into a pool

Bahama House

3 bed | 3 bath | Dogs okay

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

2 bed | 2 bath | Dogs okay

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

4 bed | 4.5 bath | No dogs

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

2 bed | 2 bath | Dogs okay

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.

private pool of two level vacation home with upper deck and a spiral staircase to pool area

The Conch-Out Cottage

1 bed | 2 bath | No dogs

Book this tropical Key West cottage just two blocks from Duval Street, with a private plunge pool, full kitchen, balcony, and eclectic decor. Walk to top spots like the Hemingway House and enjoy modern comforts in a central location.

More vacation homes in Key West with pools

You might also like...

Two vacationers snorkeling in the Florida Keys
Plan your Florida Keys snorkeling vacation
the finish line at a florida keys race
Four scenic Florida Keys races and marathons for every skill level
Anna Maria Island vacation home with outdoor private pool
Seven charming Anna Maria beach cottages for a seaside retreat
private outdoor pool of Hilton Head beach house
Dive in at these oceanfront Hilton Head vacation rentals with pools