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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
2–7 Aug
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4.92 out of 5 average rating, 225 reviews
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
2–7 Aug
5.0 out of 5 average rating, 26 reviews
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds, 8 bathrooms
8–13 Sept
New place to stay
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 29 reviews
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5 bedrooms, 7 beds, 5.5 bathrooms
7–12 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Clermont
Lux 6 bed with Pool/SPA
6 bedrooms, 10 beds, 4 bathrooms
19–24 Jul
5.0 out of 5 average rating, 8 reviews
Home in Clermont
Cozy Mod Escape | Sleeps 7 | "Oak Tree House"
3 bedrooms, 5 beds, 2 bathrooms
20–25 Jul
5.0 out of 5 average rating, 4 reviews
Home in Kissimmee
Disney World Retreat Oasis & Private Pool
5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug
New place to stay
Superhost
Home in Clermont
Family pool home w/ game room near Disney
4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Clermont
Family Fun House at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
26–31 Jul
New place to stay
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Top guest favourite
Flat in Kissimmee
Amazing 03 Bedrooms/ 03 Baths / Sleeps 08
3 bedrooms, 5 beds, 3 bathrooms
25–30 Aug
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds, 3 bathrooms
8–13 Aug
4.98 out of 5 average rating, 83 reviews
Guest favourite
Townhouse in Kissimmee
4 Beds / 4.5 Baths / Magic Village Views (3085RW)
4 bedrooms, 6 beds, 4.5 bathrooms
29 Aug – 3 Sept
4.9 out of 5 average rating, 20 reviews
Guest favourite
Villa in Clermont
Villa near Disney with complimentary spa heating!
4 bedrooms, 6 beds, 2 bathrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 10 reviews