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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, 199 reviews
Superhost
Home in Clermont
2026 Brand NEW 08 Bedrooms At Windsor Cay
8 bedrooms, 9 single beds, 6 bathrooms
13–18 Sept
New place to stay
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
19–24 Aug
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
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
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
20–25 Aug
4.9 out of 5 average rating, 58 reviews
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
19–24 Aug
5.0 out of 5 average rating, 28 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
Guest favourite
Home in Kissimmee
Disney Delight: 5BR Haven ~ 10 Min from the magic
5 bedrooms, 7 beds, 5 bathrooms
29 Aug – 3 Sept
4.86 out of 5 average rating, 59 reviews
Home in Clermont
Cozy Luxurious downtown lakeview home in Clermont
3 bedrooms, 3 beds, 2.5 bathrooms
19–24 Aug
New place to stay
Top guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 5 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, 4 reviews
Top guest favourite
Home in Kissimmee
Luxury Villa Near Parks | Private Pool & Game Room
5 bedrooms, 5 beds, 4 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 35 reviews
Superhost
Home in Kissimmee
Disney Oasis Bungalow with Palm-lined relaxation!
2 bedrooms, 4 beds, 1 bathroom
23–28 Aug
New place to stay
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Apopka
The little Manatee Home - Lake & Wildlife Retreat
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.98 out of 5 average rating, 66 reviews
Home in Kissimmee
4BR Villa | Private Pool • Minutes to Disney
4 bedrooms, 5 beds, 2 bathrooms
19–24 Aug
New place to stay
Superhost
Home in Clermont
Experience Our New 2026 10BR Home at Windsor Cay
10 bedrooms, 12 beds, 8 bathrooms
13–18 Sept