
Holiday rentals with a pool in Winter Garden
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Winter Garden
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Winter Garden rentals with a pool
House rentals with a pool

Cheerful 4 Bed, 3 Bath Home with Screened Pool
Overall the place was very nice, it was a bit pricey but cheaper than a hotel. The amount of space and sleeping accommodation were the best part of the house. Would have loved to use the pool but the water was way too cold, would have been nice to be heated. Appreciated tremendously that we were allowed to check in super early to get the opportunity to get ready for my daughters rehearsal and rehearsal dinner. Host was so accommodating and super nice. Probably the only negative things I can say is that we spotted a few roaches and there was not enough toilet paper to accommodate 11 guest which is what we had. But overall I would love to stay again.

Private pool home near Downtown
This is instantly become my favorite Airbnb. Such a wonderful and beautiful experience. It’s an absolutely fantastic location while also enjoying the aspect of privacy. This will definitely be my go to anytime that I have to come into Orlando!

Gated community XL pool Home 2500sq/f
Heidy and her husband Michael were absolutely wonderful hosts while we were visiting Lake Mary. We loved the Sanford area and all the recommendations Heidy gave us. Their home is beautiful, clean, cozy and the backyard is an absolute dream. Our girls loved the pool. It is “cannon ball approved” by my 10 yo. My husband accidentally left the garage door open when we left for Universal for the day, but Michael was notified and kindly went and closed it and checked on the house for us. We loved having them close by. They were so sweet and helpful. We had the best time on our vacation and can’t wait to visit again.

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney
This home was clean and conveniently located near a ton of things to do, paces to eat, and a short drive to Disney.

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!

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-SpaHeat-Private Pool-Remodeled
Tetyana’s place was very clean, welcoming, and felt like home away from home. It was conveniently located near Disney and easy to access. The bed was very comfortable and I slept like a baby. The master bath was a great way to unwind and relax after walking over 10,000 steps at the Disney parks. We LOVED the jacuzzi/pool combo and how secluded it was. Very quiet neighborhood, responsive host, and easy check-in. We’ll be back. :)
Apartment 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

Lovely 1 Bedroom Apartment with Pool and Jacuzzi!
We had a wonderful stay at Danny's home! It was incredibly comfortable and made us feel right at home. The amenities were fantastic, and the atmosphere was warm and inviting. Highly recommend!

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
El apartamento es muy cómodo, tiene todo lo necesario para una buena estadía con la familia y está ubicado en una zona tranquila y de fácil acceso a todo. Está cerca de los parques de Disney y cerca de toda clase de tiendas, supermercados y restaurantes. Gary es muy diligente, ofrece instrucciones claras y estuvo pendiente a que no tuviéramos problemas a la llegada.

Chic Condo + Star Wars Room | Pool & Near Disney
We had a fantastic stay here and will return! The unit was beautifully decorated, very clean, and the Disney paintings throughout were the perfect touch. While we didn’t find all of the hidden Mickey’s and Minnie’s, we had a lot of fun searching for them! Thank you for sharing this beautiful home with us!

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!
Excelente hospedaje, muy cerca de los sitios de interés de Orlando / Florida.

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

Minniehaha Castle Retreat
This house was ideal for our weekend. Everything we needed was provided, and the extras pillows, towels, and toiletries were a nice touch. The pool water heater was a great addition, making the water perfect for the time of year ($10 a day was worth it) . We enjoyed our stay and would recommend it to others.

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!

Beautiful Lakeview Retreat Drivable to Theme Parks
Todo estuvo increíble, la casa es súper grande y espaciosa y las vistas son increíbles

Sleeps 20! Near Disney w/ Pool | Twice-as-Nice
Nous étions 7 adultes et 2 enfants et cette maison était énorme. Tout le monde était content avec leur chambre. La seule de jeu était un succès. Super grand et comfortable ❤️ c’était incroyable on veut déjà retourner. La seule contrainte que nous avons eu c’était qu’on a pas comprit comment chauffer le spa. La hôte répond super vite et nous aide dans tout ce que nous avons besoin. Merci beaucoup pour ces souvenirs et beaux moments.

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

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 holiday rentals with a pool in Winter Garden
Total rentals
20 properties
Total number of reviews
220 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Local attractions
Winter Garden Downtown Pavilion and Farmers Market, Best Buy and Miller's Ale House - Winter Garden
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Disney Springs
- SeaWorld Orlando
- ESPN Wide World of Sports
- Universal Orlando Resort
- Reunion West
- Amway Center
- Kissimmee Lakefront Park
- ChampionsGate Golf Club
- Epcot
- Disney's Hollywood Studios
- Universal's Islands of Adventure
- Blue Spring State Park
- Magic Kingdom Park
- Aquatica
- ICON Park
- Island H2O Water Park
- Harry Potter and the Escape from Gringotts™