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Search results; Over 1,000 homes in Winter Garden

Superhost
Home in Winter Garden
Downtown Winter Garden Luxury Retreat (NO Parties)
3 bedrooms, 3 beds, 1 private bathroom
7–12 Sept
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4.9 out of 5 average rating, 29 reviews
Top guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 5 reviews
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
Superhost
Rooms in Oakland
Oakland Trails
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 4 reviews
Home in Clermont
25 miles to Disney Contry side house
4 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
New place to stay
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
Superhost
Home in Montverde
3BD Montverde Lakeview Escape Near Orlando
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
New place to stay
Superhost
Home in Clermont
Experience Our New 2026 10BR Home at Windsor Cay
10 bedrooms, 12 beds, 8 bathrooms
13–18 Sept
Top guest favourite
Home in Kissimmee
Golden Haven | 5BR | Pool | 12 Min to Disney
5 bedrooms, 7 beds, 4.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 6 reviews
Home in Clermont
Cozy Luxurious downtown lakeview home in Clermont
3 bedrooms, 3 beds, 2.5 bathrooms
3–8 Nov
New place to stay
Home in Kissimmee
Premium house, 4 bedrooms, sleeps 10, Kissimme
4 bedrooms, 8 beds, 3 bathrooms
1–6 Sept
New place to stay
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, 46 reviews
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.92 out of 5 average rating, 95 reviews
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
Superhost
Home in Kissimmee
6 Bd / 3,5 Ba / Sleeps 22 / Reunion Village
6 bedrooms, 11 beds, 3.5 bathrooms
7–12 Sept
New place to stay
Superhost
Home in Davenport
3BR Luxury Disney Escape | Hot Tub & 2 King Suites
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Sept
New place to stay
Guest favourite
Home in Orlando
5 Min- Epic Universe+KingBed+Disney
3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 10 reviews