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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Cottage in Winter Garden
The Heart of Winter Garden: Walk to shops & dining
2 bedrooms, 2 beds, 1 private bathroom
9–14 Sept
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4.99 out of 5 average rating, 199 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
13–18 Aug
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds, 4.5 bathrooms
14–19 Sept
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 12 reviews
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds, 2 bathrooms
2–7 Oct
New place to stay
Superhost
Home in Four Corners
8BR house at Windsor Cay Resort
8 bedrooms, 8 beds, 6 bathrooms
17–22 Aug
New place to stay
Superhost
Townhouse in Kissimmee
Unique Villa w/ Hot Tub & Minutes From Disney
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Aug
New place to stay
Home in Kissimmee
Premium house, 4 bedrooms, sleeps 10, Kissimme
4 bedrooms, 8 beds, 3 bathrooms
24–29 Aug
New place to stay
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
16–21 Aug
5.0 out of 5 average rating, 28 reviews
Guest favourite
Townhouse in Kissimmee
3 Bd/ 2.5 Ba/ Encantada Resort (3113 Yl)
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Kissimmee
Vacation Condo with pool-20 Min from Disney
2 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 7 reviews
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
5 bedrooms, 7 beds, 4.5 bathrooms
16–21 Aug
New place to stay
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 104 reviews
Home in Kissimmee
4BR Villa | Private Pool • Minutes to Disney
4 bedrooms, 5 beds, 2 bathrooms
13–18 Aug
New place to stay
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
6 bedrooms, 9 beds, 4 bathrooms
21–26 Aug
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Flat in Apopka
The little Manatee Home - Lake & Wildlife Retreat
1 bedroom, 2 beds, 1 bathroom
19–24 Aug
4.98 out of 5 average rating, 65 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Gotha
Stylish Home • Sleeps 8 • Near Disney & Universal
3 bedrooms, 6 beds, 2.5 bathrooms
16–21 Aug
New place to stay