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Search results; Over 1,000 homes in Winter Garden

Guest favourite
Guest suite in Winter Garden
Designer Guest Suite Near Disney/Universal/DT
1 bedroom, 3 beds, 1 private bathroom
30 Aug – 4 Sept
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4.84 out of 5 average rating, 416 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed
13–18 Aug
Home in Kissimmee
4BR Villa | Private Pool • Minutes to Disney
4 bedrooms, 5 beds
13–18 Aug
New place to stay
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds
14–19 Sept
Superhost
Home in Four Corners
8BR house sleeps 20 near Disney attractions
8 bedrooms, 8 beds
17–22 Aug
New place to stay
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds
20–25 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Townhouse in Kissimmee
Unique Villa w/ Hot Tub & Minutes From Disney
3 bedrooms, 4 beds
17–22 Aug
New place to stay
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds
16–21 Aug
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds
22–27 Aug
5.0 out of 5 average rating, 12 reviews
Superhost
Home in Gotha
Stylish Home • Sleeps 8 • Near Disney & Universal
3 bedrooms, 6 beds
16–21 Aug
New place to stay
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
5 bedrooms, 7 beds
16–21 Aug
New place to stay
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds
16–21 Aug
4.9 out of 5 average rating, 58 reviews
Top guest favourite
Flat in Apopka
The little Manatee Home - Lake & Wildlife Retreat
1 bedroom, 2 beds
24–29 Aug
4.98 out of 5 average rating, 66 reviews
Home in Kissimmee
4BR Kissimmee home with private pool
4 bedrooms, 5 beds
23–28 Aug
New place to stay
Superhost
Home in Davenport
3BR Luxury Disney Escape | Hot Tub & 2 King Suites
3 bedrooms, 3 beds
15–20 Aug
New place to stay
Guest favourite
Townhouse in Kissimmee
Magic Village 4 Suites w/ Jacuzzi - 7493
4 bedrooms, 7 beds
14–19 Aug
4.88 out of 5 average rating, 85 reviews
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds
23–28 Nov
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in Kissimmee
Stylish Disney Retreat | 15 Mins to Disney
3 bedrooms, 4 beds
6–11 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds
13–18 Aug
5.0 out of 5 average rating, 12 reviews