
Vacation rentals with a pool in Windsor Hills, Four Corners
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Top-rated rentals with a pool in Windsor Hills, Four Corners
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Windsor Hills, Four Corners rentals with a pool
House rentals with a pool

The Shire -Private Pool & Hot Tub, Close to parks!
This home has such a great layout. Monica was a wonderful and attentive host. This location is close to everything Orlando has to offer. The pool and hot tub were lovely. This home looked even better in person. The beds and pillows were so comfortable. We cannot wait to come back.

Disney Beautiful Home Pool and Spa
My family and I have a wonderful time at this place. All updated appliances, very clean, everything was just as we expected if not better! If I had a question she would reply in minutes! I would recommend staying here, you will not be disappointed. I hope she has an opening for when we come back in a couple months, beautiful place!

Casa El Paraiso pool house w| 5 bedrooms.
This place was absolutely fantastic... I would definitely stay again. The hosts were very responsive when needed... Amazing place to stay and enjoy... we had a family of 9 and still had more then enough room. Place was very very nice!!!!

Stylish Villa Private Pool-SPA Near Parks Disney!
Guillermo was an amazing host with a beautiful location. 10/10 would visit again.

Pool House in Kissimmee
Everything was great. We came down to see our granddaughters on spring break. Usually don’t want to swim,this time they did. Wish I would have spent the money to heat the pool. They enjoyed playing pool and wanted to play air hockey but no puck but amazon took care of that. The master on one end and other bedrooms on the opposite end was a big plus for we got up earlier so we didn’t wake them. Would definitely recommend and would love to come back next year.

4BR-2KingMasters-Private Pool-Spa*-Fully Remodeled
We were very satisfied with our stay. We were here for 1 month in January. Tatyana was always very responsive and considerate. One night the smoke alarms went off for some reason. The fire department was called and they suspected that the system was too old. Tatyana immediately had a handyman come in the next day and replace them all. Anyone’s house may need some minor maintenance from time to time. Tatyana has a regular routine of maintenance that she adheres to strictly. We felt very much at home. The property was clean. The provisions were more than adequate. Thank you Tatyana!

New Pet-Friendly Heated Pool Mini Golf Disney
our stay went great, tubanur is great at communication, she even responded once to my message after midnight. the place was as described. pool is a private area. the beds were comfortable and there were many games and activities in the house. there is a park at a walkable distance too. overall I would recommend.

Exclusive Private Stylish Paradise!
my entire family was happen with the location and how cleanednit was. I will happily come back and rent their property. my family and I are loyal customers.
Condo rentals with a pool

LUXURY RESORT & GOLF CONDO MIN CLOSE TO DISNEY
I love this place. The view was amazing. The host made me and my family feel so welcomed. The host checked on us everyday to make we were good and didn’t need anything. I really appreciate it

Pool View Family Condo Disney Universal Orlando
I’m very grateful to Laura for reserving this beautiful condo. It’s centrally located, close to attractions, and incredibly convenient. The condo is also in excellent condition. I truly appreciate the host’s attention before and during our stay — it made everything so much easier, and she was wonderfully attentive. My husband and I thoroughly enjoyed our anniversary. Eternally grateful!

Condo Minutes from Disney - No Hidden Fees
The apartment is very comfortable, it has everything you need for a good stay with the family and is located in a quiet area with easy access to everything. It is close to Disney parks and close to all kinds of shops, supermarkets and restaurants. Gary is very diligent, offers clear instructions, and was on the lookout for us to have no issues on arrival.

Chic Condo + Star Wars Room | Pool & Near Disney
Condo was so pretty, clean and easy to find! Kayla was super responsive, nice and receptive! Looked just like advertised! Will definitely come back here next time i visit the area!

Beautiful Windsor Palms Condo near Disney!
Great place! really cozy and clean, Nicolle was very helpful when we ran into some issues and made our stay the best a couple days

Lovely 3-BR Condo With Pool 5.7mi from Disney!
We have 3 children and this place was great for our family. It had everything we needed and more, location was great, and hosts communicated well. Highly recommend this place!

Lovely 3BR 2BA condo, great amenities and location
Great place to stay clean and very welcoming

Stunning condo close to everything!
Doris' place is a great location and close proximity from where we were headed. There were also plenty of restaurants and other shops/stores in the area which made it that much better. My daughters really enjoyed the pool and were happy about having a say in this selection. Most definitely a must visit.
Home rentals with a private pool

Airy, Stylish Home with Pool Heat Included in Davenport
Had a great stay at Phil’s place! The pictures matched the space and it was so cozy! The kitchen had everything you could think of needing to cook. The heated pool was the best ending to our days out in the golf course and the parks. The bed was so comfy! Close to many golf courses and just a short drive to parks. Phil was responsive anytime I reached out. We had no hot water the 2nd day in and it was fixed within the hour! We will definitely bookmark for next time!

Visit Disney World from a Sunny Home with a Pool
We really enjoyed our stay in this home. Everything was as described and the host was very responsive. We had a hiccup with no trash pick up, but the very understanding host accomodated. Internet was down most of the trip, but no fault of the host & we weren't there most of the day, so it wasn't a problem. Plenty of space, well decorated & comfortable. We used Uber & had Walmart deliver anything we needed which was right around the corner, (including alcohol!). All the parks were about a 30 ish minute ride, traffic is horrific (no matter where you are) which is why it was nice to use Uber. Awesome vacation overall!

Family Retreat Near Disney with Pool & Hot Tub!
Excellent location, beautiful decor in bedrooms and common areas, new appliances and fully equipped kitchen, beds and bathrooms clean and comfortable. If we return to Kissimmee, the entire group (adults and kids) voted to repeat the same place to stay!

Sleeps 20! Near Disney w/ Pool | Twice-as-Nice
Every aspect of the stay completely surpassed expectations. Thank you for having us!

Luxury Disney Dreams Home Pool Spa Game Room
Great stay! Highly recommend!

Amazing Dream Solterra Villa -Disney/club/pool/spa
They house is exactly like described and had a lot of room. The cleaning could be a bit better, but they apparently had a very short turn-around. Be prepared to have parties going on around you. They do not enforce the noise ordinance at midnight like they should. We were not their to party, so this did have an affect on some of our guests. Overall, it was a pleasant stay. Edward is a super host for a reason. He always returned my emails and texts. When we needed something he was sure to get it to us. He made us feel comfortable about this purchase from the very beginning.

Vacation Resort Home Right Outside of Disney World
We evacuated our coastal home ahead of a hurricane and found this pet-friendly rental to be exactly what we needed. The house was fun, which helped lift our spirits during a difficult time. However, the real highlight was the hosts, who were incredibly accommodating and gracious, making an extremely stressful situation much easier to manage.
Quick stats about vacation rentals with a pool in Windsor Hills, Four Corners
Total rentals
670 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
12K reviews
Family-friendly rentals
610 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
380 properties have a dedicated workspace
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- Universal Studios Florida
- Orange County Convention Center
- Old Town Kissimmee
- Universal's Volcano Bay
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Disney Springs
- SeaWorld Orlando
- ESPN Wide World of Sports
- Reunion West
- Amway Center
- Universal Orlando Resort
- ChampionsGate Golf Club
- Kissimmee Lakefront Park
- Universal's Islands of Adventure
- Epcot
- Disney's Hollywood Studios
- Blue Spring State Park
- Magic Kingdom Park
- Harry Potter and the Escape from Gringotts™
- ICON Park
- Aquatica
- Island H2O Water Park
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