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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Cottage in Winter Garden
The Heart of Winter Garden: Walk to shops & dining
2 bedrooms, 2 beds, 1 private bathroom
9–14 Sept
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4.99 out of 5 average rating, 197 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
4.91 out of 5 average rating, 92 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5.0 out of 5 average rating, 7 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
10–15 Aug
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
4.96 out of 5 average rating, 48 reviews, 2 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
5.0 out of 5 average rating, 26 reviews, 4 bedrooms, 6 beds, 3 bathrooms
2–7 Aug
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
New place to stay, 10 bedrooms, 16 beds, 8 bathrooms
8–13 Sept
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5.0 out of 5 average rating, 29 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
25–30 Aug
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
Superhost
Home in Clermont
Family pool home w/ game room near Disney
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5.0 out of 5 average rating, 18 reviews, 5 bedrooms, 7 beds, 5.5 bathrooms
7–12 Aug
Guest favourite
Home in Clermont
Lux 6 bed with Pool/SPA
5.0 out of 5 average rating, 8 reviews, 6 bedrooms, 10 beds, 4 bathrooms
19–24 Jul
Home in Clermont
Cozy Mod Escape | Sleeps 7 | "Oak Tree House"
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 5 beds, 2 bathrooms
20–25 Jul
Home in Kissimmee
Disney World Retreat Oasis & Private Pool
New place to stay, 5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug
Superhost
Home in Clermont
Family Fun House at Windsor Cay
New place to stay, 5 bedrooms, 7 beds, 4.5 bathrooms
26–31 Jul
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
4.98 out of 5 average rating, 83 reviews, 3 bedrooms, 4 beds, 3 bathrooms
8–13 Aug
Top guest favourite
Flat in Kissimmee
Amazing 03 Bedrooms/ 03 Baths / Sleeps 08
4.97 out of 5 average rating, 36 reviews, 3 bedrooms, 5 beds, 3 bathrooms
25–30 Aug
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept