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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
13–18 Jul
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4.9 out of 5 average rating, 92 reviews
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
23–28 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Windermere
Relaxing 2BR Lakeview Retreat Close to Attractions
2 bedrooms, 3 beds, 1 bathroom
15–20 Jul
4.99 out of 5 average rating, 116 reviews
Superhost
Home in Kissimmee
Greek Villa w/ Sunny Pool just 20 Min to Disney
4 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
New place to stay
Top guest favourite
Townhouse in Kissimmee
3 BD/ 3 BA/ The Hub At Westside (3349 TT)
3 bedrooms, 5 beds, 3 bathrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
15–20 Jul
4.89 out of 5 average rating, 55 reviews
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, 3 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
29 Aug – 3 Sept
New place to stay
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
23–28 Jul
5.0 out of 5 average rating, 11 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
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom, 1 king bed, 1 bathroom
21–26 Jul
4.97 out of 5 average rating, 34 reviews
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds, 8 bathrooms
15–20 Aug
New place to stay
Superhost
Home in Clermont
Brand NEW 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4 bathrooms
27 Sept – 2 Oct
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
6 bedrooms, 9 beds, 4 bathrooms
2–7 Aug
4.98 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
26–31 Jul
5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in Kissimmee
Orlando Dream Escape | Private Pool | Disney
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.86 out of 5 average rating, 7 reviews
Superhost
Townhouse in Davenport
NEW Disney Resort Free Waterpark Private Pool Gym
4 bedrooms, 6 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Superhost
Townhouse in Clermont
Brand 2026 NEW 05 Bdrms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
7–12 Oct
5.0 out of 5 average rating, 3 reviews