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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Guest house in Winter Garden
A place with a view
2 bedrooms, 3 beds, 1 private bathroom
3–8 Aug
,
4.9 out of 5 average rating, 105 reviews
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds
10–15 Aug
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds
29 Aug – 3 Sept
New place to stay
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds
19–24 Jul
4.91 out of 5 average rating, 93 reviews
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds
8–13 Sept
New place to stay
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds
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
2–7 Aug
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds
20–25 Sept
Superhost
Home in Clermont
Family pool home w/ game room near Disney
4 bedrooms, 5 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Clermont
Lux 6 bed with Pool/SPA
6 bedrooms, 10 beds
19–24 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5 bedrooms, 7 beds
7–12 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Clermont
2026 NEW Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 8 beds
11–16 Oct
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Clermont
Family Fun House at Windsor Cay
5 bedrooms, 7 beds
26–31 Jul
New place to stay
Home in Kissimmee
Disney World Retreat Oasis & Private Pool
5 bedrooms, 7 beds
2–7 Aug
New place to stay
Home in Davenport
5BR Florida villa with private pool
5 bedrooms, 5 beds
2–7 Aug
New place to stay
Superhost
Home in Kissimmee
Disney 7 Min • Luxury 4 Suites • Jacuzzi • Arcade
4 bedrooms, 8 beds
1–6 Aug
New place to stay
Home in Clermont
Cozy Mod Escape | Sleeps 7 | "Oak Tree House"
3 bedrooms, 5 beds
20–25 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds
8–13 Aug
4.98 out of 5 average rating, 83 reviews