Southwest Florida vacation rentals with pools

We found 538 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 Southwest Florida vacation homes where you can dive in, cool off, and catch some sun.

Top-rated Southwest Florida rentals with pools

Our guests have spoken. Explore their favorite and top-rated homes in Southwest Florida with refreshing pools, sun-splashed decks, and poolside seating.

Parrot Beach Cottages Suite #3
1 Bed | 1 Bath | Sleeps 4 (2 Adults Max)

Parrot Beach Cottages Suite #3 - Siesta Key, FL

From $234
(excludes fees and taxes)
4.19 (79)
Parrot Beach Cottages Suite #2
0 Bed | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #2 - Siesta Key, FL

From $228
(excludes fees and taxes)
4.62 (86)
Parrot Beach Cottages Suite #1
0 Bed | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #1 - Siesta Key, FL

From $205
(excludes fees and taxes)
4.49 (81)
Whiskey Creek
3 Bed | 2.5 Bath | Sleeps 8

Whiskey Creek - Fort Myers, FL

From $242
(excludes fees and taxes)

Explore All Vacation Rentals With Pools

Recent guest reviews

Loved staying at this house my family of four and parents. Very clean and great location near beach and all that north Naples has to offer. Loved the pool and outdoor shower!
Nikki M. | Jul 2025
This was a perfect setup. House was very clean and had everything we could want. The kitchen had all the items to cook if you wanted and plates dishes, cutlery, ect. The bathrooms had plenty of towels,washcloths, shampoo, conditioner and soap. The pool was wonderful and they had pool towels. The tiki dock area was great for fishing which is one of the reasons I picked this one. The booking, arrival and departure were effortless. Also when I messaged my questions, I always got a quick response. I would stay again.
Jennifer F. | Jul 2025
Great location, great amenities. We will book again.
Nicole A. | Jul 2025
Loved the pool and patio area. Loved the location of the home. Close to shopping, restaurants and fun-in-the-sun activities.
Rebecca Z. | Jul 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 in Southwest Florida

Dog-friendly
Hot tub
Internet
Electric vehicle charger
Lake view
Lakefront
Ocean view
Oceanfront

Nearby destinations

Gulf Coast
Florida Gulf Coast
South Florida
Everglades National Park
Punta Gorda Isles
Bonita Beach
Manasota Key
Pine Island
USA > Florida > Southwest Florida > Pool