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Search results; Over 1,000 homes in Winter Garden

Superhost
Home in Winter Garden
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
4 bedrooms, 4 beds, 2.5 private bathrooms
20–25 Sept
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4.95 out of 5 average rating, 149 reviews
Flat in Winter Garden
Studio Apt close to Downtown & Bike Trail, Apt #3
1 bedroom, 1 king bed, 1 bathroom
12–17 Sept
Home in Orlando
Luxury 2BR Home | Private Patio & Stylish Stay
2 bedrooms, 2 king beds, 1 bathroom
25–30 Sept
New place to stay
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 35 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.92 out of 5 average rating, 97 reviews
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
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
Top guest favourite
Home in Kissimmee
Amazing 3Bdrms/2,5bath At Encantada
3 bedrooms, 5 beds, 2.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 10 reviews
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
Superhost
Home in Kissimmee
Comfy Villa W/ Pool & FREE BBQ | Near Disney
4 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
New place to stay
Room in Winter Garden
J&K Accommodation
4 beds, 1 bathroom
12–17 Sept
New place to stay
Flat in Kissimmee
Majik Vacation Home
3 bedrooms, 4 beds, 3 bathrooms
12–17 Sept
New place to stay
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, 88 reviews
Top guest favourite
Townhouse in Kissimmee
Disney, 4Bd, 3 Baths, Wi-Fi, Private Pool
4 bedrooms, 1 king bed, 3 bathrooms
18–23 Sept
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Kissimmee
Designer Townhome 3Bed/3Bath | 15 min to Disney
3 bedrooms, 6 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 29 reviews
Home in Orlando
Top Rated Family Resort Near Disney & Universal
2 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
New place to stay
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
Top guest favourite
Flat in Clermont
Downtown Clermont Scenic Retreat
2 bedrooms, 2 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 14 reviews
Superhost
Home in Kissimmee
4BR house with private pool in Paradise Palms
4 bedrooms, 5 beds, 3 bathrooms
12–17 Sept
New place to stay