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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
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
4.91 out of 5 average rating, 92 reviews, 3 bedrooms, 4 beds, 2 bathrooms
11–16 Jul
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
10–15 Aug
Guest favourite
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
5.0 out of 5 average rating, 8 reviews, 7 bedrooms, 10 beds, 5.5 bathrooms
6–11 Mar
Home in Clermont
Cozy Mod Escape |Sleeps 7| "Oak Tree House"
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 5 beds, 2 bathrooms
17–22 Jul
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
Home in Kissimmee
Magic-Ready 4BR Pool Home Near Disney
New place to stay, 4 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5.0 out of 5 average rating, 16 reviews, 5 bedrooms, 7 beds, 5.5 bathrooms
26–31 Jul
Superhost
Home in Kissimmee
2026 Brand New Themed 06 Bedrooms At Solara Resort
6 bedrooms, 2 beds, 5 bathrooms
22–27 Aug
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
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
4.98 out of 5 average rating, 83 reviews, 3 bedrooms, 4 beds, 3 bathrooms
16–21 Aug
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
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
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
Superhost
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
Top guest favourite
Flat in Apopka
The little Manatee Home - Lake & Wildlife Retreat
4.98 out of 5 average rating, 58 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Aug
Guest favourite
Townhouse in Kissimmee
4 Beds / 4.5 Baths / Magic Village Views (3085RW)
4.89 out of 5 average rating, 18 reviews, 4 bedrooms, 6 beds, 4.5 bathrooms
2–7 Aug
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
5.0 out of 5 average rating, 24 reviews, 4 bedrooms, 6 beds, 3 bathrooms
12–17 Jul