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, 502 reviewsThe Groves (1)
Sep 21 – 28
Home in Clermont
4.93 out of 5 average rating, 187 reviewsLake Front Home with private Dock on Lake Louisa
Jul 29 – Aug 5
Home in Winter Garden
4.9 out of 5 average rating, 20 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 12 – 19
Tiny home in Winter Garden
4.93 out of 5 average rating, 40 reviewsEnchanted TINY HOME SUITE - Downtown Winter Garden
Sep 11 – 18
Home in Winter Garden
4.94 out of 5 average rating, 17 reviewsCozy home in Winter Garden
Jul 16 – 23
Home in Winter Garden
4.93 out of 5 average rating, 86 reviewsLuxury Home Winter Garden Near Disney & Universals
Sep 12 – 19
Farm stay in Winter Garden
4.96 out of 5 average rating, 45 reviewsCarriage House Studio Apt Peaceful & Private Ranch
Oct 11 – 18
Other great vacation rentals in Winter Garden
Home in Clermont
5.0 out of 5 average rating, 18 reviewsLakefront home - country setting
Sep 21 – 28
Home in Winter Garden
4.9 out of 5 average rating, 42 reviewsWinter Garden Experience
Oct 21 – 28
Apartment in Minneola
4.98 out of 5 average rating, 48 reviewsSpacious Apartment In Minneola
Aug 20 – 27
Apartment in Windermere
5.0 out of 5 average rating, 19 reviews1BR Cozy Oasis+King Bed+Fast WiFi+Pool+Gym
Mar 2 – 9
Home in Clermont
4.98 out of 5 average rating, 44 reviewsDownton Clermont Luxury Suite
Sep 8 – 15
Guest suite in Apopka
4.97 out of 5 average rating, 30 reviewsPrivate Deluxe Apartment, 1000 sqft with pool
May 9 – 16
Apartment in Ocoee
4.96 out of 5 average rating, 50 reviewsCompletely Private and Cozy Studio
Oct 3 – 10
Condo in Windermere
5.0 out of 5 average rating, 14 reviewsLuXury Apt with Lake View, Cable & fast WiFi
Jul 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 200 vacation rentals in Tildenville, and over 50 vacation rentals in Johns Lake Point.
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.
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