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Search results; Over 1,000 homes in Winter Garden

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Superhost
Home in Winter Garden
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
4 bedrooms, 4 beds, 2.5 private bathrooms
4–9 Oct
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4.95 out of 5 average rating, 150 reviews
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Flat in Winter Garden
Studio Apt close to Downtown & Bike Trail, Apt #3
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
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Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
4–9 Oct
4.94 out of 5 average rating, 35 reviews
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Home in Gotha
Private Pool Retreat Mins to Universal & Disney
4 bedrooms, 6 beds, 2 bathrooms
28 Nov – 3 Dec
New place to stay
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Guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 8 reviews
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Home in Orlando
Luxury 2BR Home | Private Patio & Stylish Stay
2 bedrooms, 2 king beds, 1 bathroom
23–28 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.92 out of 5 average rating, 98 reviews
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Superhost
Home in Kissimmee
The Happily Ever After Hideaway
3 bedrooms, 4 beds, 2 bathrooms
19–24 Oct
New place to stay
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Home in Kissimmee
Disney Luxury Escape Private Pool 4BR BBQ
4 bedrooms, 5 beds, 3 bathrooms
21–26 Oct
New place to stay
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Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
3 bedrooms, 3 queen beds, 2.5 bathrooms
7–12 Oct
5.0 out of 5 average rating, 89 reviews
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Top guest favourite
Home in Kissimmee
Home, Private Pool, 10 min to Disney, 3 BR/2 Baths
3 bedrooms, 5 beds, 2 bathrooms
1–6 Nov
4.98 out of 5 average rating, 47 reviews
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Flat in Kissimmee
Vacation Villa 5 min From Disney #27
1 bedroom, 3 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Superhost
Townhouse in Davenport
Spacious 5-BR Villa with Private Pool / Families
5 bedrooms, 8 beds, 4.5 bathrooms
8–13 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds, 5.5 bathrooms
2–7 Nov
5.0 out of 5 average rating, 24 reviews
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Superhost
Home in Kissimmee
NEW 2026 Themed 9BR| Racing Simulator |Solara
9 bedrooms, 13 beds, 6.5 bathrooms
14–19 Dec
4.75 out of 5 average rating, 4 reviews
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Superhost
Townhouse in Clermont
5Bd/ 4Ba/ Windsor Cay Resort (16197 Pf)
5 bedrooms, 7 beds, 4.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Superhost
Townhouse in Clermont
5 Bd/ 4.5 Ba/ Windsor Cay (1252 Bi)
5 bedrooms, 9 beds, 4.5 bathrooms
2–7 Nov
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Orlando
12BR Disney Luxury Retreat - Pool, Theater & Fun!
12 bedrooms, 21 beds, 11.5 bathrooms
13–18 Oct
4.98 out of 5 average rating, 58 reviews
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Apartment in Orlando
4114-306 Spacious 3bd condo at Vista Cay Resort
3 bedrooms, 7 beds, 2 bathrooms
9–14 Nov
5.0 out of 5 average rating, 3 reviews