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Search results; Over 1,000 homes in Winter Garden

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Top guest favourite
Cottage in Winter Garden
The Swift House
1 bedroom, 1 bed, 1 private bathroom
18–23 Sept
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4.88 out of 5 average rating, 42 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
21–26 Sept
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Home in Orlando
Luxury 2BR Home | Private Patio & Stylish Stay
2 bedrooms, 2 king beds, 1 bathroom
25–30 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 97 reviews
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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 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
Villa in Oakland
Historic Oakland Manor House
5 bedrooms, 5 beds, 6.5 bathrooms
19–24 Sept
4.91 out of 5 average rating, 54 reviews
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Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.9 out of 5 average rating, 58 reviews
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Guest favourite
Room in Winter Garden
Haven 15 minutes from Disney
1 bed, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Clermont
Lake Front Home with private Dock on Lake Louisa
3 bedrooms, 4 beds, 2 bathrooms
2–7 Oct
4.94 out of 5 average rating, 228 reviews
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Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom, 1 king bed, 1 bathroom
19–24 Sept
4.98 out of 5 average rating, 53 reviews
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Superhost
Home in Montverde
3BD Montverde Lakeview Escape Near Orlando
3 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
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
4–9 Oct
5.0 out of 5 average rating, 89 reviews
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Home in Davenport
Memory Maker | King + Queen • Lazy River • Disney
4 bedrooms, 6 beds, 3 bathrooms
19–24 Sept
New place to stay
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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
27 Sept – 2 Oct
4.98 out of 5 average rating, 46 reviews
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Flat in Windermere
15 Min to Disney | Family 1BR w/ Balcony + Pool
1 bedroom, 3 beds, 1 bathroom
6–11 Oct
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Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 215 reviews
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Room in Ocoee
Bedroom and private bathroom
1 queen bed, 1.5 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Kissimmee
Magical Getaway: 2-BR Near Disney
2 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
4.92 out of 5 average rating, 13 reviews