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Search results; Over 1,000 homes in Winter Garden

Guest favourite
Flat in Winter Garden
Stay A While
1 bedroom, 3 beds, 1 private bathroom
17–22 Sept
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4.89 out of 5 average rating, 169 reviews
Flat in Winter Garden
Studio Apt close to Downtown & Bike Trail, Apt #3
1 bedroom, 1 king bed, 1 bathroom
13–18 Sept
Home in Orlando
Luxury 2BR Home | Private Patio & Stylish Stay
2 bedrooms, 2 king beds, 1 bathroom
13–18 Sept
New place to stay
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
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
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
20–25 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
Top guest favourite
Home in Kissimmee
Home, Private Pool, 10 min to Disney, 3 BR/2 Baths
3 bedrooms, 5 beds, 2 bathrooms
1–6 Nov
4.98 out of 5 average rating, 46 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
6 BD/ 6 BA/ Encore Resort at Reunion (480 Ld)
6 bedrooms, 7 beds, 6 bathrooms
3–8 Oct
New place to stay
Flat in Kissimmee
Close to everything, spacious, and comfortable
3 bedrooms, 5 beds, 2 bathrooms
31 Oct – 5 Nov
New place to stay
Flat in Orlando
Enormous studio apartment in the heart of Orlando
1 bedroom, 1 queen bed, 1 bathroom
16–21 Sept
New place to stay
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
Superhost
Apartment in Kissimmee
Neverland Hideaway At Caribe Cove
2 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
Superhost
Home in Kissimmee
NEW Lois Ann's Disney Landing 4 miles to entrance!
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Nov
New place to stay
Superhost
Home in Kissimmee
4BR house with private pool in Paradise Palms
4 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
New place to stay
Top guest favourite
Home in Kissimmee
Magic Stay near Disney
2 bedrooms, 3 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Flat in Clermont
Downtown Clermont Scenic Retreat
2 bedrooms, 2 beds, 1.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 14 reviews