Published October 19, 20263 min readBeach

Florida Keys Rentals with Pool Access

This list is for families and groups looking for a Key West or Florida Keys rental with a private pool or access to a shared pool. It includes 11 rentals in our Florida Keys directory whose own websites (the property’s site or its manager’s booking page) mention a pool. We checked each site on October 19, 2026. Seven of these homes have a pool that is not shared: the site calls it private, or the home is rented as a whole house. The other four share a pool at a condo complex or gated community, so ask the host about hours and rules.

Quick answer

The 11 rentals below are grouped alphabetically, not ranked, and show no ratings or prices. Each line also lists other features the same site mentions. For the full, filterable set, see Florida Keys rentals with a pool.

How we checked

A rental appears here only when two things agree: our directory data tags it with a pool, and its own website mentioned a pool when we loaded it on October 19, 2026. We left out rental companies, resorts and other multi-unit sites, where a mention may not apply to one unit, including a compound of five rentals that share one pool. We also left out a studio whose pool access is through a neighboring resort. Each line says whether the site describes a pool that is private to the rental or one shared with a complex or community. Features change, so treat this as a starting point and confirm with the host.

Rentals whose sites mention a pool

04 - Poolside by the Sea. Its site describes a shared heated outdoor pool at the condo property, a few steps from the unit. It also mentions waterfront, grill, washer, dryer, kitchen and wifi.
11 - Keys Time. Its site describes a shared heated outdoor pool at the condo property, a few steps from the unit. It also mentions waterfront, grill, washer, dryer, kitchen and wifi.
Anglers Reef Vacation Rental. Its site describes a swimming pool in the gated community, shared with the other homes there. It also mentions grill, washer, dryer, dishwasher, kitchen and wifi.
Best Marathon House. Its site lists a private heated pool with a spa at the home.
Casa Azul Villa. Its site describes a pool at the villa, which is rented as a whole house, so the pool is not shared with other guests. The site says there is no hot tub. It also mentions kitchen.
Casa Feliz Florida Keys. Its site describes a pool and spa at the home, which is rented as a whole house, so the pool is not shared with other guests. It also mentions king bed, balcony, deck, grill, kitchen and wifi.
Henry's Piece Of Paradise. Its site describes the shared heated pool and hot tub at the 1800 Atlantic condo complex.
Key West Oasis – 2BR, 2BA with Pool House. Its site describes a private heated pool at the home. It also mentions kitchen.
Seaside Place Key West. Its site describes a large heated pool at this five-bedroom Old Town home, which is rented as a whole house, so the pool is not shared with other guests. It also mentions kitchen.
Turtle Cove, Marathon. Its site describes a private pool and hot tub at the home. It also mentions waterfront, king bed, balcony, deck, grill and washer.
William Skelton Home. Its site describes a private heated pool at the home. It also mentions grill and kitchen.

Questions to ask before you book

Is the pool private to this rental or shared with other guests or a community?
Which months is it open, and is it heated?
Are there age, hour or lifeguard rules?

FAQ

Does BnB Search rank these rentals?

No. BnB Search is a vacation rental directory. This list is unranked and shows no ratings; you book on each property’s own site.

How do you know each one has a pool?

Each rental’s own website mentioned a pool when we checked it on October 19, 2026, and our listing data tags it with one. Confirm with the host, since features can change.