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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Home in Winter Garden
Downtown Winter Garden, Florida
2 bedrooms, 2 beds, 1 private bathroom
1–6 Sept
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4.99 out of 5 average rating, 159 reviews
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds
14–19 Sept
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed
15–20 Aug
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds
23–28 Aug
4.92 out of 5 average rating, 95 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Gotha
Stylish Home • Sleeps 8 • Near Disney & Universal
3 bedrooms, 6 beds
16–21 Aug
New place to stay
Home in Kissimmee
4BR Villa | Private Pool • Minutes to Disney
4 bedrooms, 5 beds
15–20 Aug
New place to stay
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds
23–28 Aug
4.98 out of 5 average rating, 87 reviews
Superhost
Home in Davenport
7 Bd/ 5.5 Ba/ Windsor Island Resort (3409 Lw)
7 bedrooms
20–25 Aug
New place to stay
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds
22–27 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Kissimmee
Luxury Villa Near Parks | Private Pool & Game Room
5 bedrooms, 5 beds
24–29 Aug
5.0 out of 5 average rating, 35 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds
3–8 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds
16–21 Aug
4.9 out of 5 average rating, 58 reviews
Superhost
Townhouse in Kissimmee
4 Bd/ 3 Ba/ Lucaya Village (8-101)
4 bedrooms, 7 beds
30 Aug – 4 Sept
Superhost
Flat in Orlando
New luxury 3BD in Vista Cay · 5 min Epic Universe
3 bedrooms, 6 beds
21–26 Aug
5.0 out of 5 average rating, 4 reviews
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds
6–11 Sept
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
6 bedrooms, 9 beds
21–26 Aug
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds
15–20 Aug
5.0 out of 5 average rating, 12 reviews