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Search results; Over 1,000 homes in Winter Garden

Guest favourite
Home in Winter Garden
NoAirbnbFees/Disney5m/Fish/HotTub/3Pool/Gym/Courts
2 bedrooms, 2 beds, 2 private bathrooms
1–6 Aug
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4.9 out of 5 average rating, 93 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed
1–6 Aug
New place to stay
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds
5–10 Aug
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
12–17 Oct
New place to stay
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds
1–6 Aug
4.89 out of 5 average rating, 56 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds
1–6 Aug
5.0 out of 5 average rating, 11 reviews
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds
28 Aug – 2 Sept
Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
3 bedrooms, 3 queen beds
18–23 Sept
5.0 out of 5 average rating, 80 reviews
Guest favourite
Home in Clermont
Stunning 5B/4.5B, Heated Pool & BBQ
5 bedrooms, 7 beds
2–7 Aug
5.0 out of 5 average rating, 18 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds
10–15 Aug
New place to stay
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5 bedrooms, 7 beds
19–24 Aug
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Clermont
2026 Cozy Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds
22–27 Sept
5.0 out of 5 average rating, 24 reviews
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
5 bedrooms, 7 beds
16–21 Aug
New place to stay
Guest favourite
Home in Clermont
2026 NEW Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 8 beds
7–12 Feb
5.0 out of 5 average rating, 6 reviews
Superhost
Townhouse in Four Corners
Gorgeous Villa w/ Mickey Room, Private Pool & More
4 bedrooms, 8 beds
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Home in Kissimmee
Stylish Disney Retreat | 15 Mins to Disney
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds
6–11 Sept
5.0 out of 5 average rating, 11 reviews
Home in Four Corners
The Epic Escape Mansion 9Br near Disney/Universal
9 bedrooms, 20 beds
9–14 Aug
New place to stay
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds
8–13 Aug
5.0 out of 5 average rating, 13 reviews