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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Cottage in Winter Garden
The Heart of Winter Garden: Walk to shops & dining
2 bedrooms, 2 beds, 1 private bathroom
9–14 Sept
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4.99 out of 5 average rating, 196 reviews
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5.0 out of 5 average rating, 7 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
23–28 Jul
Top guest favourite
Townhouse in Clermont
The gold cottage
4.89 out of 5 average rating, 55 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Jul
Superhost
Home in Clermont
Brand NEW 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4 bathrooms
27 Sept – 2 Oct
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5.0 out of 5 average rating, 17 reviews, 5 bedrooms, 7 beds, 5.5 bathrooms
26–31 Jul
Guest favourite
Home in Clermont
Lux 6 bed with Pool/SPA
5.0 out of 5 average rating, 7 reviews, 6 bedrooms, 10 beds, 4 bathrooms
19–24 Jul
Superhost
Home in Kissimmee
Greek Villa w/ Sunny Pool just 20 Min to Disney
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
Superhost
Home in Clermont
Family pool home w/ game room near Disney
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 5 beds, 2 bathrooms
23–28 Jul
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
New place to stay, 7 bedrooms, 6 beds, 4.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Townhouse in Kissimmee
3 BD/ 3 BA/ The Hub At Westside (3349 TT)
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 5 beds, 3 bathrooms
28 Jul – 2 Aug
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
New place to stay, 10 bedrooms, 16 beds, 8 bathrooms
15–20 Aug
Superhost
Townhouse in Davenport
NEW Disney Resort Free Waterpark Private Pool Gym
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 6 beds, 3 bathrooms
27 Sept – 2 Oct
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
5.0 out of 5 average rating, 25 reviews, 4 bedrooms, 6 beds, 3 bathrooms
26–31 Jul
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
4.98 out of 5 average rating, 48 reviews, 6 bedrooms, 9 beds, 4 bathrooms
2–7 Aug
Superhost
Townhouse in Kissimmee
3 BD/ 2.5 BA/ Encantada Resort (3113 YL)
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
3–8 Aug
Guest favourite
Home in Kissimmee
Orlando Dream Escape | Private Pool | Disney
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug