
House holiday rentals in Winter Garden
Find and book unique houses on Airbnb
Top-rated house rentals in Winter Garden
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Winter Garden
House rentals with a pool

Private pool home near Downtown
Kyle was a very responsive and friendly host. We especially noted the little details and home amenities of the place. Light switches were labeled, which was a great help. The location is in walking distance to some of Orlando’s very best restaurants. Fantastic stay overall!

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
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
Our host was very nice. House was clean and cute. Only issue we had was the 2nd bathroom being outside. Other than that we had a great stay. Very close to shopping and restaurants!

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

Country Pool home on 2 acres-30 minutes to Disney
This was the perfect location for our family! The kids enjoyed the pool and swings. We enjoyed everything about the home. We would definitely book this home 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.

Retreat Race
Beautiful, spacious and clean home. Great stay. Hope to be back in the future.
Weekly house rentals

Pet-Friendly Bungalow Near Downtown Orlando
Megan's place was everything we needed. We felt right at home and my dog was very happy with the house and the backyard. Totally fenced in yard was safe and secure for my fur baby and the neighborhood was super quiet and cute. Megan was very responsive if I had any questions and the instructions to get in were super easy. I am so very pleased with the comfort of the beds and how wonderful the space was. I will definitely be staying here again hopefully soon. If you need a safe, pet friendly place to stay close to just about everything this is the place for you and your pets. Highly recommend!!!!! 5 stars from me and my 4 legged friend.

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

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

3/2 Family Home, climatized Pool and Sunset Views
The house was very clean and in a nice area. It was a great place to come back and relax after the day’s activities. The view through the back door was excellent too!

BRAND NEW 10Bedrms/Sleeps22 At Windsor Island
Bruce’s place was great. We had a family of 11. There were enough rooms for everyone, and the place matched the pictures. This was our first time staying at a resort, and it was worth it. The only problem we had was the long lines getting into the resort(they could use a second entrance, but it did not impact our overall stay! We had questions for Bruce, and each time he answered in a timely manner!

Spacious 4 bedroom single story home
This home is one the most wonderful place we’ve stayed in. Lovely kitchen complete with so many items to cook a family dinner. Beautiful lanai with comfortable seating and lovely plants. And the back garden is beautiful as well with many flowering plants this time of year. Ronald was very accommodating by solving all the minor problems. Loved our stay here.

Spacious 4BR Near All Florida Attractions!
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
Can't say enough great things about Jonathan and his place! We loved staying there, felt right at home, we were there with 5 kids and there was always something fun for them to do, swimming in the pool and hot tub, s'mores by the fire, pool, air hockey, pacman was a hit, basketball, and lots of games, books and movies to choose from. There was plenty of space to spread out and feel comfortable and Jonathan added so many thoughtful touches to our stay - greeting us with an Apple Pie on the kitchen counter, a bowl of chocolates in the entry way and plenty of coffee. The kitchen was fully stocked with everything we needed, there were plenty of towels for showers and swimming, life jackets were supplied. The kids said they wanted to move there : ). Need I say more? haha

Jas Vacation Home
Great place for my family to spend Christmas together. The place had enough space, quite, easy access, and mostly the kitchen space was more than enough to cook a holiday dinner.

Private luxury home w additional Suite on 0.6 acre
My family and I travel all around the world. This is by far one of the best Airbnb we have ever stayed at truly a home away from home. The house is excellent. The host is amazing. Always willing to help in whatever way he can. Thank you very much for a wonderful stay.We will definitely stay with you again.

Private Haven: Free Pool Heat & BBQ/5Bedroom/4.5Ba
Pam’s place was lovely and a perfect place for our vacation. The heated pool was very appreciated, and there were plenty of towels, blankets, soap, dishes, blankets etc. The house was exactly as pictured and very spacious. Pam was very helpful with instructions and checked in regularly. We had no issues during our stay but we felt if anything did occur Pam would have been responsive which was nice to know. We would definitely recommend this place and would stay again if we came back to Orlando.

Pelican House
Our family had a great stay at The Pelican House. Donna was very responsive and friendly. The house matched its description. Very clean, comfy beds and close to all the parks. Thank you for the outstanding stay.

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.

Sunset Cove at Champions! Book this very private
This lovely home was exactly as described. Located near the end of a gated street, but within 20 minutes of many restaurants. It also had the best selection of kitchen supplies and the nicest washer & dryer I’ve ever seen in a rental. Sue was a pleasure to work with!! We hope to return next year.

Quiet Home Near the Springs
Glenn's place was great! It was extremely clean and all the essentials were available. We loved the swing on the porch and the quality linens. The kiddo said "5 stars!"
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
Destinations to explore
- Orlando Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Central Florida Holiday rentals
- Saint Johns River Holiday rentals
- Tampa Holiday rentals
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Seminole Holiday rentals
- Fort Lauderdale Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Family-friendly rentals Winter Garden
- Rentals with outdoor seating Winter Garden
- Flat rentals Winter Garden
- Rentals with a washing machine and dryer Winter Garden
- Rentals with pools Winter Garden
- Rentals with a patio Winter Garden
- Pet-friendly rentals Winter Garden
- Villa rentals Winter Garden
- House rentals Orange County
- House rentals Florida
- House rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Universal Studios Florida
- Orange County Convention Center
- Old Town Kissimmee
- Universal's Volcano Bay
- Reunion Resort Golf Courses - Palmer & Watson
- Disney's Animal Kingdom Theme Park
- Discovery Cove
- Disney Springs
- SeaWorld Orlando
- ESPN Wide World of Sports
- Reunion West
- Amway Center
- ChampionsGate Golf Club
- Universal Orlando Resort
- Kissimmee Lakefront Park
- Universal's Islands of Adventure
- Epcot
- Ventura Country Club
- Disney's Hollywood Studios
- Blue Spring State Park
- Magic Kingdom Park
- Harry Potter and the Escape from Gringotts™
- ICON Park
- Universal CityWalk