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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Home in Winter Garden
Downtown Bungalow with fire pit and putting green
2 bedrooms, 2 beds, 1 private bathroom
1–6 Sept
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4.97 out of 5 average rating, 132 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
New place to stay, 1 bedroom, 1 bed, 1 bathroom
1–6 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
1–6 Aug
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
4.91 out of 5 average rating, 93 reviews, 3 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
New place to stay, 10 bedrooms, 16 beds, 8 bathrooms
12–17 Oct
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
4.97 out of 5 average rating, 39 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 beds, 5 bathrooms
28 Aug – 2 Sept
Room in Ocoee
Bedroom and private bathroom
New place to stay, 1 queen bed, 1.5 bathrooms
7–12 Aug
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
5.0 out of 5 average rating, 80 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
18–23 Sept
Apartment in Kissimmee
*NEW* 3BR/2BA Condo w/ pool, steps to Disney
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Home in Four Corners
The Epic Escape Mansion 9Br near Disney/Universal
New place to stay, 9 bedrooms, 20 beds, 5 bathrooms
9–14 Aug
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
New place to stay, 5 bedrooms, 7 beds, 4.5 bathrooms
16–21 Aug
Home in Ocoee
Serenity Retreat
New place to stay, 2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Townhouse in Clermont
The gold cottage
4.89 out of 5 average rating, 56 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Superhost
Home in Four Corners
7 BD/ 5.5 BA/ Windsor Cay (1036 BP)
7 bedrooms, 10 beds, 5.5 bathrooms
23–28 Aug
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 4 bathrooms
8–13 Aug
Guest favourite
Home in Clermont
Stunning 5B/4.5B, Heated Pool & BBQ
5.0 out of 5 average rating, 18 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
2–7 Aug
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
New place to stay, 4 bedrooms, 8 beds, 3.5 bathrooms
9–14 Aug