
House holiday rentals in Winter Garden
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Top-rated house rentals in Winter Garden
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Holiday rentals for every style
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Popular amenities for house rentals in Winter Garden
House rentals with a pool

Cheerful 4 Bed, 3 Bath Home with Screened Pool
Great place to stay.

Private pool home near Downtown
My girlfriend and I enjoyed our stay. It’s a great place to stay if you want somewhere quiet and peaceful. There’s plenty of places to eat nearby. Very clean and it looked like the pictures and smelled good when we walked in.

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.

Gated community XL pool Home 2500sq/f
We love staying at Heidi’s homes! She is always so wonderful! It will be an annual thing as long as we can book.

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney
Very Relaxing getaway for us visiting from New York, love the outdoor pool and the beautiful backyard

SUPER DOPE- FUN/Electric Home W/POOL & AMENITIEs!
Justin's service is amazing, all the personnel is attentive and kind, they communicate very quickly. We found this place after another host canceled on us on the check in day, not only was it available Justin's team were very helpful and understanding with the situation. The house is spacious and was very clean, the neighborhood felt very safe and convenient to get to different places. Check out process was smooth, instructions were very simple and not demanding (as in other places). Would recommend this listing and other Justin's listings because the service was spectacular.

Country Pool home on 2 acres-30 minutes to Disney
We had a fantastic stay. Property was as described. Clean with a lot of privacy. Check-in and check-out were both easy. The pool, playground, and outdoor seating enhanced our family stay. Host was friendly and was easy to communicate with. Would stay again.

Carrera retreat
Really clean and comfortable home. The pool and amenities are as listed. The host was so responsive and helpful.
Weekly house rentals

Pet-Friendly Bungalow Near Downtown Orlando
Perfect for our trip! Loved the pet friendly atmosphere while still being clean! If we had a cat the catio would have been so fun! The plants were so nice too. Easy check out and the beds very comfy! Megan was a great host!

Weekly Discount!8Br/6Ba Villa-Pool-Near Disney
I must say Ruibin was awesome. When I reached out to ask questions he would respond within minutes. My entire family loved the home. The home is beautiful, and as described. There is so much space for everyone. Thanks to Ruibin, my family and I had a wonderful vacation.

9001-WW 5 Bedroom ALL Suites Pool Home
Found this air b&b last minute and late due to having to leaving our precious air b&b. Magic was very helpful and responsive on such short notice. I’m so thankful we found this place my kids absolutely loved it and they will remember it forever! It was very clean. They were also very accommodating. Had an issue with the dishwasher but it was quickly fixed. We absolutely loved it, thank you again!! You made our vacation amazing. Perfect house for our Disney Christmas surprise. We will be back.

5BD Windsor Westside Private Pool (WW 9025)
Jose is very friendly and respond most of the time within 15 minutes. Easy to talk to. We loved the place. We were already familiar with the subdivision and the area. We were with 6 and had plenty of rooms and bathrooms

Family-Friendly 3BR Home w/ Pool Beautiful Sunsets
Ana’s home was perfect for our family getaway with an infant. The home was very clean, had all the amenities we needed including a pack n play and high chair. Ana had her home decorated so cute for Valentine’s Day. Grocery store and restaurant 5 min. drive. Beautiful sunsets and unique birds to watch on the pond. Hot tub really not any warmer than the pool but still enjoyed. We’d definitely come back! Thanks for being a great host Ana!

Villa with Guest House & Pool-Patio
Wonderful stay! The house was perfect. This was my second time staying there. My daughter goes to school near by and I came for a visit. House is as described and has everything you need! Yard is fantastic and peaceful! Felt so comfortable at this house!

BRAND NEW 10Bedrms/Sleeps22 At Windsor Island
Our stay started complicated, due to an error in the Airbnb system that allowed two reservations to be made for the same lodging. So when we arrived our house was busy, which was very stressful. However, Bruce was very helpful in solving our problem, relocating us to another house. Even after we had to relocate again, Bruce did his best to mitigate the resulting disorders and communication was very easy with him. The house is amazing and just like the announcement. It would certainly recommend the house and the host to anyone.

4-Bedroom Townhouse Resort Near Theme Parks
Evening was as depicted, we really enjoyed the home and the area is really quiet and really close to everything ! Thank you again Michelle for a seamless journey and we will definitely book again !
Private house rentals

Lake Whistler Beach House with lakefront pool
Couldn’t be happier with our stay!! Great space for teammates playing at Lake Myrtle Sports park, even close enough to wait out a lightning delay. Was a great place to stay in to watch a big game and enjoy a game night. We didn’t get out on the lake, but we’ll be back to enjoy more next time. Host was exceptional!

969T-Single Storey House 20 min from Disney 4 bed
Loved this property, it had everything we needed for a thanksgiving weekend. Publix was 8 mins away, very large driveway. And they supplied the bathrooms with plenty of tissue paper. A lot to do on the property such as fire pit and game room

Private luxury home w additional Suite on 0.6 acre
The home was beautiful. Nice quiet area. Definitely a lot of space for a large family! Awesome decor and very clean. The only downfall for us is it was a little further from Disneyland than we wanted to be. However have we of had more time to relax and enjoy the house it would have been perfect. If our next visit is not so rushed then we would definitely consider this beautiful spacious home again.

Private Haven: Free Pool Heat & BBQ/5Bedroom/4.5Ba
This was a great place to stay for a Disney trip!! It was close to the parks (15 minutes with little traffic and 30-40 minutes with heavy traffic). It was also close to lots of restaurants and stores that made for ease of getting food and supplies we needed. We had a couple of issues that came up that Pam was very helpful and responsive to! Pam was a great host!!

Sleeps 10 * House + Apt *Pool*Near Disney*GolfView
Walk in the door of the main house and first thing is “wow.” Spaciousness and high ceilings and the view all the way through to the back windows of the golf course was impressive. Neighborhood very walkable and safe Little traffic within the complex for kids. Nice to have easy driveway parking right out front for unloading. Plenty of space to fit my people. Nicely decorated and not full of a bunch of bling on end tables and shelves that the kids would run into and break. I was not just clean but had a sense of clean, design-wise, with the modern but comfy furniture, giant kitchen island, table surfaces… all that and, again, the spaciousness gives you the ability to breathe! But it still had a homey feel – way better than a hotel setting where we would have all been on top of each other. The cute coffee station was a really nice touch with everything you needed right there in one spot off the kitchen. Because the house is set back on the property it was like a real get-away, and with the guest house, my parents were able to have their privacy and we could have ours – when we needed it. The guest house is exactly what they needed. Separated from main house it is perfect for the grandparents to spend alone time with the kids for a while. But it’s also like a real house by itself! Very open and comfortable – and a great view of the action in the pool and courtyard. Pool is just big enough to enjoy and with the protective fence, you don’t really have to worry about the kids running around in the yard – that was also a nice touch. And even though there’s a Wa Wa right outside the complex gate, for quick lunches and coffee – and gas – we discovered an area ChampionsGate, a suburban community with all the restaurants and shops and places to do errands. About a 5-10 minute drive. Lastly, I really liked the big walk-in shower, and my partner absolutely loved the big tub – all that in the en suite bathroom off the master bedroom. It was out of the way and private – like our own a retreat spot.

Quiet Home Near the Springs
House is exactly as described. Perfect place for two with a great lanai to have dinner and relax in the swing chair. Will definitely be back!

318 BD - Disney Dream House
Edney was an amazing host! His communication was quick and helpful, ensuring we had everything we needed for a comfortable stay. The house was breathtaking – extremely clean, spacious, and thoughtfully designed with every detail in mind. It far exceeded our expectations! We highly recommend staying here and would gladly return in the future. Thank you, Edney, for making our stay unforgettable!

Entire House Davenport My Dream House
An excellent, very cozy place to spend a vacation both inside and outside the hotel. Very nice, excellent place. I hope to visit this place again and find it available. Thank you very much.
Quick stats about house rentals in Winter Garden
Total rentals
70 properties
Total number of reviews
2.8K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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