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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 Bungalow with fire pit and putting green
2 bedrooms, 2 beds, 1 private bathroom
16–21 Sept
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4.97 out of 5 average rating, 133 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
16–21 Sept
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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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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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Guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
24–29 Sept
5.0 out of 5 average rating, 8 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
4–9 Oct
5.0 out of 5 average rating, 89 reviews
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Home in Orlando
Luxury 2BR Home | Private Patio & Stylish Stay
2 bedrooms, 2 king beds, 1 bathroom
25–30 Sept
New place to stay
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Guest favourite
Home in Kissimmee
Charming 3BR Home Near Disney with Comfort & Conve
3 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 7 reviews
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Superhost
Home in Kissimmee
Private Pool • No Resort Fee | 10 Min to Disney
4 bedrooms, 5 beds, 2 bathrooms
8–13 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Clermont
Downtown Clermont Scenic Retreat
2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 14 reviews
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Room in Winter Garden
J&K Accommodation
4 beds, 1 bathroom
16–21 Sept
New place to stay
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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 Kissimmee
Comfy Villa W/ Pool & FREE BBQ | Near Disney
4 bedrooms, 6 beds, 3 bathrooms
5–10 Oct
New place to stay
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Superhost
Home in Kissimmee
Family fun with private pool & bathtub near disney
3 bedrooms, 5 beds, 2.5 bathrooms
22–27 Sept
New place to stay
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Superhost
Townhouse in Clermont
5 Bd/ 4.5 Ba/ Windsor Cay (1252 Bi)
5 bedrooms, 9 beds, 4.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 3 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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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 Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
2–7 Oct
4.94 out of 5 average rating, 35 reviews
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Superhost
Apartment in Kissimmee
Neverland Hideaway At Caribe Cove
2 bedrooms, 5 beds, 2 bathrooms
10–15 Nov