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Search results; Over 1,000 homes in Winter Garden

Guest favourite
Home in Winter Garden
Cozy Winter Garden Home 20 MINUTES FROM DISNEY
1 bedroom, 1 bed, 1 private bathroom
6–11 Aug
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4.92 out of 5 average rating, 225 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
6–11 Aug
New place to stay
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds, 2 bathrooms
6–11 Aug
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
10–15 Aug
5.0 out of 5 average rating, 14 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
New place to stay
Townhouse in Davenport
Solterra resort townhouse w/ private pool
4 bedrooms, 5 beds, 3.5 bathrooms
31 Aug – 5 Sept
New place to stay
Superhost
Home in Clermont
Game room + pool home near Orlando's top parks
4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Four Corners
7 Bd/ 5.5 Ba/ Windsor Cay (1036 Bp)
7 bedrooms, 10 beds, 5.5 bathrooms
23–28 Aug
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Flat in Orlando
Spacious2BR PetsFriendly Oasis Sleeps6, Pool & Gym
2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
6–11 Aug
5.0 out of 5 average rating, 27 reviews
Room in Ocoee
Bedroom and private bathroom
1 queen bed, 1.5 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Flat in Orlando
Luxury 1BR & Resort Amenities - 6min to Epic-Uni
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 6 reviews
Home in Clermont
New! Windsor Cay Resort | Private Pool | 5BR/5.5BA
5 bedrooms, 6 beds, 5.5 bathrooms
16–21 Aug
New place to stay
Superhost
Flat in Orlando
New luxury 3BD in Vista Cay · 5 min Epic Universe
3 bedrooms, 6 beds, 2 bathrooms
21–26 Aug
New place to stay
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
23–28 Aug
Guest favourite
Home in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds, 5.5 bathrooms
3–8 Sept
5.0 out of 5 average rating, 21 reviews
Superhost
Townhouse in Clermont
5 BD/ 4.5 BA/ Windsor Cay (16218 CC)
5 bedrooms, 7 beds, 4.5 bathrooms
18–23 Oct