Stock Island vacation rentals with pools

We found 6 vacation rentals waiting for you.

Find your ultimate splash pad

From plunge pools for a quick dip to infinity pools with a view, here are the Stock Island vacation homes where you can dive in, cool off, and catch some sun.

Top-rated Stock Island rentals with pools

Our guests have spoken. Explore their favorite and top-rated homes on Stock Island with refreshing pools, sun-splashed decks, and poolside seating.

Hemingway Hideaway
3 Bed | 3 Bath | Sleeps 6

Hemingway Hideaway - Key West, FL

From $521
(excludes fees and taxes)
4.33 (112)
Tropical Retreat
3 Bed | 2.5 Bath | Sleeps 6

Tropical Retreat - Key West, FL

From $285
(excludes fees and taxes)
5.0 (7)
The Tipsy Mermaid at Key West Golf Club
3 Bed | 2.5 Bath | Sleeps 6

The Tipsy Mermaid at Key West Golf Club - Key West, FL

From $190
(excludes fees and taxes)
4.5 (12)
Tarpon Watch
2 Bed | 2 Bath | Sleeps 6

Tarpon Watch - Key West, FL

From $215
(excludes fees and taxes)
5.0 (3)

Explore All Vacation Rentals With Pools

Recent guest reviews

Cannot say enough about this rental. It is an overall experience and leaves you wanting for nothing. The unit is well appointed, spacious and checks off all boxes for a wonderful vacation in Key West. The views are spectacular and the sunsets are to die for. Exceeds any expectations and the fact that it was large enough to accommodate our entire family was priceless. 10 out of 10 for sure.
Chris H. | Jul 2025
The home is located on the gulf side in a secure, gated community. We enjoyed the beautiful sunsets, as well as watching boats go by in the marina. The home was well equipped for a longer stay, and was clean and well maintained. We also like being in a quiet neighborhood, but with a short Uber ride to Old Town.
Rick H. | Jul 2025
We thoroughly enjoyed our time at Sunset Bay in Key West during the singer-songwriter festival. Overall, our stay was excellent. We found the home to be very clean and well-maintained, and it appeared to have been recently updated, which was a pleasant surprise. We particularly appreciated how quiet the property was, allowing for restful nights after enjoying the festival events. And the sunsets were the best we’ve seen in key west! Thank you for providing such a wonderful accommodation for our visit. Best regards, Al & Courtney
Al and Courtney S. | May 2025
The house was extremely nice. The neighbors and community were extremely nice and gracious. It was far enough from downtown to be quiet and close enough to take a golf cart. Landscaping was immaculate. Wish I had brought my golf clubs - the course looked great. Gated and secluded is hard to find in Key West.
Phillip H. | May 2025
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FAQ

Our vacation rentals offer both private and shared pools. Each property’s listing description will specify whether the pool offered is private or shared.

Every home is stocked with plenty of towels. However, the availability of pool towels varies by property.

Some pools are heated, and there may be an additional fee for this service. You can find more information about heating fees in the property description.

Yes, pool maintenance is included during your stay. We ensure that pools and hot tubs are regularly cleaned and maintained to provide an optimal experience. If you encounter any issues with the pool during your stay, contact our Guest Experience team immediately.

Many of our properties include lounge chairs, umbrellas, or shaded areas by the pool, but this can vary. Check the property details and listing photos for specific details.

Generally, food and drinks are allowed by—but not in—the pool. However, to be safe, it’s best not to use glass or china in the pool area.

Pool toys, floaties, or inflatables are typically not provided. You may want to bring your own, if needed.

Some properties include a poolside grill or outdoor kitchen area, but this is not standard across all rentals. Check the property listing for details.

We have a good neighbor policy that includes quiet hours from 10 p.m. to 8 a.m. In addition, certain communities have noise policies in place. Unauthorized parties are not allowed, and excessive noise can lead to intervention and removal from a property.

If you encounter any issues with the pool during your stay, contact our Guest Experience team immediately. Your local Vacasa team will work to resolve the problem as quickly as possible.

Not all pools are open all year round. Some pools—depending on the destination—are seasonal only. Read the listing description for specific operating times for the pool.

More ways to stay on Stock Island

Dog-friendly
Hot tub
Internet
Lake view
Ocean view
Oceanfront
Sound view
Soundfront

Nearby destinations

Gulf Coast
Florida's Atlantic Coast
South Florida
Southeast Florida
Florida Keys
Lower Keys, FL
Key West
Florida
USA > Florida > Stock Island > Pool