House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Garden house rentals
House rentals with a pool
Home in Orlando
5 out of 5 average rating, 109 reviewsPrivate pool home near Downtown
Great location in Downtown Orlando. Very clean and neat property. Felt very comfortable. Host was very responsive. Highly recommend.
Home in Davenport
4.91 out of 5 average rating, 124 reviewsThe 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.
Home in Lake Mary
4.89 out of 5 average rating, 247 reviewsGated community XL pool Home 2500sq/f
We had a wonderful visit! The house was beautiful and it was so nice to have a “place of our own” with little ones. It is also located in a very convenient location- super close to I-4 to head into Orlando or the beach. The city of Lake Mary also has everything you’d need right there within a 3-4 minute drive! The only bummer (very minimal) was that the main tv in the sitting area had a remote that was glitchy (hard to operate) and there was not a heated pool or hot tub which is quite cold in December! The kids still swam though and had lots of fun! Highly recommend…it was our first experience with an Airbnb and it did not disappoint!
Home in Orlando
4.87 out of 5 average rating, 185 reviewsPool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney
Great stay in every aspect! Highly recommend.
Home in Davenport
4.83 out of 5 average rating, 12 reviewsSplash & Play ~ Poolside Bliss ~ 15 Mins to Disney
My family and I really enjoyed the place and will definitely book again. The pool was great to help us relax after Disney and Sea world. The kitchen was well equipped and helped save a ton.
Home in Davenport
4.85 out of 5 average rating, 20 reviewsBeautiful stylish Home in Davenport
We came here to celebrate my son's 16th birthday with two of his friends. He was really wanting to swim (in January) so I was on the search for a house with a heated pool that could accommodate all of us. The check in instructions were excellent and we really loved the home. The boys spent alot of time at the pool, hot tub, and in the garage playing pool and other games. I loved the fireplace. It was a beautiful home in a great location close to many restaurants and not far from theme parks and such. The only cons are that there were barely any forks or teaspoons to use, but we really didn't need them since we mostly had fast food. Also, remember to bring your own bars of soap. I guess I'm just used to other places having some for the guests. Not big issues but I figured it was worth mentioning so you can be prepared.
Home in Clermont
4.92 out of 5 average rating, 144 reviewsStylish Villa Private Pool-SPA Near Parks Disney!
Guillermo was an amazing host with a beautiful location. 10/10 would visit again.
Home in Apopka
4.87 out of 5 average rating, 128 reviewsCountry Pool home on 2 acres-30 minutes to Disney
Was quiet and peaceful and close to stores and food. Very clean and cozy place with plenty of room
Weekly house rentals
Home in Orlando
4.9 out of 5 average rating, 20 reviewsPet-Friendly Bungalow Near Downtown Orlando
Meg's place has a great location in a quiet neighborhood. Lots of great restaurants nearby, grocery store, easy access to a number of Orlando area attractions, and very pet friendly. Good off-street parking and great backyard for a dog. Really nice set-up for 3-4 people for a few days.
Home in Kissimmee
4.84 out of 5 average rating, 180 reviewsWeekly 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.
Home in Kissimmee
4.95 out of 5 average rating, 21 reviews9001-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.
Home in Clermont
4.97 out of 5 average rating, 175 reviewsCaribe Villa Brisa- Disney is only 6 miles away!
This house was perfectly located close to Disney and other attractions. Checking in was easy and communication was great. The pool was excellent. My daughter almost preferred to leave Disney early to go back to the house and get in the pool. The home was very private, quiet, and peaceful. Plenty of room for large families!! We will definitely be returning in the future.
Home in Kissimmee
4.9 out of 5 average rating, 121 reviews5BD Windsor Westside Private Pool (WW 9025)
Nice space for a group of 5 adults
Home in Kissimmee
4.76 out of 5 average rating, 133 reviewsFamily-Friendly 3BR Home w/ Pool Beautiful Sunsets
for the price it's a great place to stay quiet neighborhood it is a little distance from Disney resorts and downtown Orlando
Home in Kissimmee
4.92 out of 5 average rating, 103 reviewsSUPER NEAT- SLEEPs 17 W/Private Pool w/AMENITIEs!
Justin was a great host who was very responsive. The house was great and there was so much space.
Home in Davenport
4.89 out of 5 average rating, 9 reviewsBRAND NEW 2024 10Bedrms/Sleeps22 At Windsor Island
Beautiful home, and very happy we chose this airbnb. My family enjoyed our time there. We will be returning
Private house rentals
Home in Auburndale
4.94 out of 5 average rating, 153 reviewsLake Whistler Beach House with lakefront pool
This was our third stay at Jonathan's place, and it is still one of our favorite Airbnb places. Jonathan is an excellent host, and the house is amazing. Our kids always ask to go back. Thank you Jonathan!
Home in Davenport
4.78 out of 5 average rating, 46 reviews969T-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
Home in Davenport
4.5 out of 5 average rating, 12 reviewsFamily house w/free WiFi, near Disney & Champion G
The stay was fantastic. We would rent again. Nice neighborhood.
Home in Kissimmee
5 out of 5 average rating, 4 reviewsWow House PLUS Apartment*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.
Home in Clermont
4.85 out of 5 average rating, 200 reviewsGIVE DISNEY FLORIDA 3/2
The stay was very very good.
Home in Apopka
4.94 out of 5 average rating, 172 reviewsQuiet Home Near the Springs
Great quiet spot within 30 minutes to anything in Orlando! Great communication with the host!
Home in Casselberry
4.93 out of 5 average rating, 100 reviewsVilla with Guest House & Pool-Patio
Such a gem! In a quiet, safe, friendly neighborhood yet accessible to plentiful shops and dining. The home is spotless and well furnished, with abundant linens and appropriate kitchenware, all located intuitively. The pool/patio area is comfortable and gorgeous. We felt immediately "at home" during our visit - it seemed like whenever I wanted to set something down, there was a perfect spot right there to set it! Jose was communicative and helpful, and he has made his rental very cozy and live-able. We will return!
Home in Davenport
5 out of 5 average rating, 5 reviews318 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!
Quick stats about house rentals in Winter Garden
Total rentals
60 properties
Total number of reviews
2.7K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 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 Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- Central Florida Vacation rentals
- Saint Johns River Vacation rentals
- Tampa Vacation rentals
- Tampa Bay Vacation rentals
- St Petersburg Vacation rentals
- Fort Lauderdale Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Miami Vacation rentals
- House rentals United States
- Lighthouse rentals United States
- Earth house rentals United States
- Guesthouse rentals United States
- Townhouse rentals United States
- Townhouse rentals Florida
- Lakehouse rentals Florida
- Beach house rentals Florida
- Guesthouse rentals Florida
- Tiny house rentals Florida
- House rentals Florida
- Lakehouse rentals Central Florida
- House rentals Central Florida
- Townhouse rentals Central Florida
- Tiny house rentals Central Florida
- Guesthouse rentals Central Florida
- House rentals Orlando
- Guesthouse rentals Orlando
- Tiny house rentals Orlando
- Townhouse rentals Orlando
- Lakehouse rentals Orlando
- Guesthouse rentals Orange County
- Tiny house rentals Orange County
- House rentals Orange County
- Townhouse rentals Orange County
- Rentals with a washer and dryer Winter Garden
- Pet-friendly rentals Winter Garden
- Apartment rentals Winter Garden
- Rentals with a patio Winter Garden
- Family-friendly rentals Winter Garden
- Rentals with pools Winter Garden
- Rentals with outdoor seating Winter Garden
- Villa rentals Winter Garden
- Monthly Rentals Winter Garden
- 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