Winter Garden vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Winter Garden
Guests agree: these vacation rentals 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 vacation rentals
Stay near Winter Garden's top sights
Other great vacation rentals in Winter Garden
Guest suite in Orlando
4.81 out of 5 average rating, 501 reviewsThe Groves (1)
Sep 27 – Oct 4
Guest suite in Orlando
4.97 out of 5 average rating, 212 reviews2/2 Spacious Modern House
Jun 19 – 26
Apartment in Winter Park
4.95 out of 5 average rating, 282 reviewsGet a Little Glam in a Retro Palm Beach-Style Boudoir
Feb 17 – 24
Home in Winter Garden
4.89 out of 5 average rating, 18 reviewsPet Friendly Winter Garden Get-Away near Orlando
May 13 – 20
Guesthouse in Winter Garden
4.94 out of 5 average rating, 49 reviewsBlue Heron Bungalow
Dec 24 – 31
Home in Winter Garden
4.94 out of 5 average rating, 17 reviewsCozy home in Winter Garden
Jul 22 – 29
Home in Winter Garden
4.93 out of 5 average rating, 86 reviewsLuxury Home Winter Garden Near Disney & Universals
Sep 24 – Oct 1
Tiny home in Winter Garden
4.93 out of 5 average rating, 40 reviewsEnchanted TINY HOME SUITE - Downtown Winter Garden
Dec 6 – 13
Other great vacation rentals in Winter Garden
Apartment in Windermere
4.83 out of 5 average rating, 53 reviewsPrivate Garage Apt., 5 Miles from Disney World
Jul 29 – Aug 5
Cottage in Clermont
4.96 out of 5 average rating, 55 reviewsA-Frame Cottage near Disney, Universal, & Lakes
Aug 16 – 23
Townhouse in Clermont
4.96 out of 5 average rating, 48 reviewsThe silver cottage
Aug 28 – Sep 4
Apartment in Windermere
4.94 out of 5 average rating, 18 reviews1BDR+Peaceful Stay+FastWifi+ Free Parking+Pool+Gym
Sep 10 – 17
Home in Clermont
5.0 out of 5 average rating, 17 reviewsLakefront home - country setting
Sep 2 – 9
Home in Clermont
4.96 out of 5 average rating, 24 reviewsUpdated Downtown Clermont Suite 837
Mar 1 – 8
Cottage in Winter Garden
4.9 out of 5 average rating, 87 reviews3 br/2 ba Downtown Winter Garden Cottage w\fence
Apartment in Ocoee
4.96 out of 5 average rating, 48 reviewsCompletely Private and Cozy Studio
May 21 – 28
Quick stats about vacation rentals in Winter Garden
Total rentals
100 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
3.6K reviews
Frequently Asked Questions
Where should I stay in Winter Garden?
Make yourself at home in Winter Garden by choosing from our most frequently booked neighborhoods. We have over 50 vacation rentals in Johns Lake Point, and over 200 vacation rentals in Tildenville.
Are there vacation rentals with a dedicated workspace in Winter Garden?
Yes! Work meets play with ease at over 40 vacation rentals in Winter Garden featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winter Garden?
Four-legged friends are welcome in Winter Garden. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there Winter Garden vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Winter Garden, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Winter Garden have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Winter Garden. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winter Garden have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in Winter Garden. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winter Garden have wifi?
Absolutely! We offer over 60 house rentals with wifi in Winter Garden. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winter Garden?
Winter Garden has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Destinations to explore
- Orlando Vacation rentals
- Kissimmee Vacation rentals
- Tampa Vacation rentals
- Anna Maria Island Vacation rentals
- Sarasota Vacation rentals
- West Palm Beach Vacation rentals
- Naples Vacation rentals
- Boca Raton Vacation rentals
- Fort Lauderdale Vacation rentals
- Miami Beach Vacation rentals
- Miami Vacation rentals
- Key West Vacation rentals
- 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