Windsor Hills Resort - Kissimmee, FL vacation rentals with pools

We found 8 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 Windsor Hills Resort - Kissimmee, FL vacation homes where you can dive in, cool off, and catch some sun.

Top-rated Windsor Hills Resort - Kissimmee, FL rentals with pools

Our guests have spoken. Explore their favorite and top-rated homes at Windsor Hills Resort - Kissimmee, FL with refreshing pools, sun-splashed decks, and poolside seating.

The Cozy Cove
3 Bed | 3 Bath | Sleeps 8

The Cozy Cove - Kissimmee, FL

From $185
(excludes fees and taxes)
Chilla Villa - Windsor Hills
3 Bed | 3 Bath | Sleeps 6

Chilla Villa - Windsor Hills - Kissimmee, FL

From $151
(excludes fees and taxes)
4.17 (29)
Almaton Magic
3 Bed | 2 Bath | Sleeps 8

Almaton Magic - Kissimmee, FL

From $117
(excludes fees and taxes)
4.3 (37)
Yellow Starfish - Windsor Hills
3 Bed | 2 Bath | Sleeps 6

Yellow Starfish - Windsor Hills - Kissimmee, FL

From $176
(excludes fees and taxes)
4.72 (18)

Explore All Vacation Rentals With Pools

Recent guest reviews

Even though it was a condo with multiple levels, we never heard anything else! The pool and water park were super nice and the short walk to basketball and tennis courts was nice as well. Traffic was the worst part, but that has nothing to do with condo, that is just Orlando unfortunately.
Stuart Lee H. | Jul 2025
Great resort, really nice home,couple of small issues, nothing serious. Excellent cable package if you’re interested in hockey
Rodney R. | Apr 2025
The home and the service
Sally T. | Apr 2025
The home was is a nice gated community with a great pool and other amenities in the pool area. It was also really close to everything including Disney. We would definitely stay again.
LYNETTE E. | Mar 2025
Best pricing

Book directly on Vacasa.com for the lowest rates.

3D virtual tours

Know exactly what you’re booking—no surprises.

Seamless check-in

Check in easily and quickly with a digital code.

Expert cleaning

Arrive to a spotless home with fresh linens.

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 at Windsor Hills Resort - Kissimmee, FL

Hot tub
Internet
Water view
A/C
Elevator
Washer/dryer
Balcony
Pack-N-Play

Nearby destinations

Central Florida
Disney World
Universal Studios Orlando
SeaWorld Orlando
Disney Springs
Kissimmee
Florida
USA > Florida > Windsor Hills Resort - Kissimmee, FL > Pool