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Search results; Over 1,000 homes in Winter Garden

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Superhost
Home in Winter Garden
Cozy Winter Garden Home 20 MINUTES FROM DISNEY
1 bedroom, 1 bed, 1 private bathroom
14–19 Sept
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4.92 out of 5 average rating, 225 reviews
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Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
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Home in Kissimmee
Pool Home 10min from Disney
4 bedrooms, 8 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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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
18–23 Sept
5.0 out of 5 average rating, 85 reviews
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Guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 6 reviews
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Superhost
Home in Kissimmee
8 Bd/ 6.5 Ba/ Solara Resort (2326 Cs)
8 bedrooms, 11 beds, 6.5 bathrooms
7–12 Sept
New place to stay
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Superhost
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.92 out of 5 average rating, 96 reviews
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Room in Ocoee
Bedroom and private bathroom
1 queen bed, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Superhost
Home in Kissimmee
4BR house with private pool in Magic Village
4 bedrooms, 6 beds, 4.5 bathrooms
1–6 Sept
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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
10–15 Sept
4.94 out of 5 average rating, 227 reviews
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Superhost
Home in Montverde
3BD Montverde Lakeview Escape Near Orlando
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
New place to stay
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Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 28 reviews
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Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.96 out of 5 average rating, 49 reviews
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Top guest favourite
Flat in Orlando
Modern 2BR Escape | King Bed • Pets • Epic U10 min
2 bedrooms, 3 beds, 2 bathrooms
2–7 Sept
5.0 out of 5 average rating, 44 reviews
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Top guest favourite
Flat in Clermont
Downtown Clermont Scenic Retreat
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom, 1 king bed, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 49 reviews
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Guest favourite
Townhouse in Kissimmee
Upstay Modern Home Near Disney with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 13 reviews
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Superhost
Home in Kissimmee
NEW 2026 Themed 9BR| Racing Simulator |Solara
9 bedrooms, 13 beds, 6.5 bathrooms
20–25 Sept
New place to stay
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Top guest favourite
Townhouse in Kissimmee
3 Bd/ 2.5 Ba/ Encantada Resort (3113 Yl)
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 8 reviews