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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
17–22 Aug
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4.9 out of 5 average rating, 94 reviews
Superhost
Home in Montverde
3BD Montverde Lakeview Escape Near Orlando
3 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
New place to stay
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
17–22 Aug
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds, 4.5 bathrooms
31 Aug – 5 Sept
Superhost
Home in Clermont
2026 Brand NEW 08 Bedrooms At Windsor Cay
8 bedrooms, 9 single beds, 6 bathrooms
23–28 Aug
New place to stay
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
25–30 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
4.98 out of 5 average rating, 87 reviews
Home in Clermont
Cozy Luxurious downtown lakeview home in Clermont
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Aug
New place to stay
Top guest favourite
Home in Kissimmee
Luxury Villa Near Parks | Private Pool & Game Room
5 bedrooms, 5 beds, 4 bathrooms
24–29 Aug
5.0 out of 5 average rating, 35 reviews
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds, 2 bathrooms
31 Oct – 5 Nov
New place to stay
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
17–22 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Kissimmee
Magical Getaway: 2-BR Near Disney
2 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds, 5.5 bathrooms
3–8 Sept
5.0 out of 5 average rating, 21 reviews
Superhost
Home in Gotha
Stylish Home • Sleeps 8 • Near Disney & Universal
3 bedrooms, 6 beds, 2.5 bathrooms
28 Aug – 2 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
23–28 Nov
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
18–23 Aug
4.9 out of 5 average rating, 58 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 5 reviews