Windsor Island Resort - Davenport vacation rentals with pools

We found 26 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 Island Resort - Davenport vacation homes where you can dive in, cool off, and catch some sun.

Top-rated Windsor Island Resort - Davenport rentals with pools

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

Explore All Vacation Rentals With Pools

Recent guest reviews

Townhouse

We enjoyed our vacation and the entire booking process was easy! Will rent again!
Amy P. | Jan 2026

House

The house was as described and met our needs The community is nice.
Kelly T. | Jan 2026

Townhouse

Overall, the house delivers exactly what was advertised. We were a group of 9 people. Everyone slept well. Important points: - Location: Far from everything. Anywhere you go in Orlando will take 40-50 minutes. Lots of traffic to get to the house due to the parks. There's a Publix supermarket 5 minutes from the house (by car). I recommend staying in Kissimmee. - Condominium: Lots of traffic to get in! Even after check-in, it will take 10 minutes or more to access the entrance gate. Somewhat chaotic (Christmas period). The clubhouse is nice, but the pool is NOT heated. They say it's warm, but it's less freezing. Very crowded. No chairs to sit on. The condominium is very secure. - The House: Needs some repairs (more love). The sofa is broken. The backrest is loose and it's dangerous for children to lean on it and break the living room window. Very few pots and pans and kitchen utensils. There was no blender. There's half of one, but it doesn't work. The refrigerator filter was expired. We bought water every day. The pool bathroom was clogged and the humidity fan was broken. Painting - Walls are stained and need touch-ups. - Shower: If two people shower at the same time, the water gets FREEZING! We went through this for 10 days. We had to alternate showers (there were 9 of us!). - Cleaning: We found a Band-Aid stuck to the guest bed. I sent a message to the Vacasa team, but nothing was done. Cutlery was a little dirty. - Pool: A decent size to enjoy, good temperature. There is an extra fee. The barbecue grill was included, but we had to buy gas as it was empty.
Hugo S. | Jan 2026

House

This is a beautiful home in a gated community. The house was incredibly clean and well prepared for our stay. We really appreciated the ample supply of towels, so we didn’t have to constantly reuse the same ones. The kitchen was well stocked, which made preparing meals very easy. The gated resort offered plenty of amenities to keep us entertained. We had read reviews about the gate and came prepared, so even though there was a short wait, we had no issues getting through once it was our turn.
DENNIS, RIVERA S. | Jan 2026
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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 at Windsor Island Resort - Davenport

Dog-friendly
Hot tub
Internet
A/C
Fireplace
Washer/dryer
Bikes
Golf on-site

Nearby destinations

Central Florida
Disney World
Universal Studios Orlando
SeaWorld Orlando
Four Corners - FL
Davenport
Florida
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