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Search results; Over 1,000 homes in Winter Garden

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Top guest favourite
Home in Winter Garden
Downtown Winter Garden, Florida
2 bedrooms, 2 beds, 1 private bathroom
1–6 Oct
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4.99 out of 5 average rating, 161 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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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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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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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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Superhost
Home in Clermont
Lake Louisa Retreat - Your Clermont Retreat.
4 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
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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 Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.92 out of 5 average rating, 97 reviews
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Top guest favourite
Flat in Kissimmee
Magical getaway: 2-bedroom property near Disney.
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
4.92 out of 5 average rating, 13 reviews
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Home in Clermont
25 miles to Disney Contry side house
4 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 3 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 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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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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Superhost
Home in Clermont
10 Bd/ 8 Ba/ Windsor Cay (1003 Cr)
10 bedrooms, 15 beds, 8 bathrooms
16–21 Nov
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Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
4.9 out of 5 average rating, 58 reviews
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Top guest favourite
Home in Clermont
Cozy Clermont Retreat
6 bedrooms, 9 beds, 4 bathrooms
1–6 Oct
4.98 out of 5 average rating, 52 reviews
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Superhost
Home in Kissimmee
7 Bd/ 6 Ba/ Storey Lake (4585 sq ft)
7 bedrooms, 10 beds, 6 bathrooms
1–6 Oct
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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
Home in Kissimmee
9BR house sleeps 24 with spa and pool
9 bedrooms, 14 beds, 5 bathrooms
29 Oct – 3 Nov
New place to stay