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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, 198 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds
1–6 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds
1–6 Aug
4.91 out of 5 average rating, 93 reviews
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds
31 Aug – 5 Sept
New place to stay
Home in Clermont
Lakeview Pool & Spa Retreat w/ Private Theater
4 bedrooms, 5 beds
29 Aug – 3 Sept
New place to stay
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds
8–13 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom, 1 king bed
1–6 Aug
4.97 out of 5 average rating, 38 reviews
Superhost
Home in Kissimmee
Disney 7 Min • Luxury 4 Suites • Jacuzzi • Arcade
4 bedrooms, 8 beds
2–7 Aug
New place to stay
Superhost
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds
16–21 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Kissimmee
Jungle pool home w/ hot tub - close to Disney
4 bedrooms, 7 beds
17–22 Aug
New place to stay
Home in Kissimmee
5BR Villa near Disney | Game Room, Pool & Hot Tub
5 bedrooms, 8 beds
1–6 Aug
New place to stay
Top guest favourite
Home in Kissimmee
Brand New Designer Townhome | 10 Min to Disney
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 25 reviews
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Home in Kissimmee
Sleeps 13-Park Shuttle-Themed Rooms-Solara Resort
5 bedrooms, 8 beds
1–6 Aug
New place to stay
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds
12–17 Sept
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds
6–11 Aug
Guest favourite
Villa in Clermont
Villa near Disney with complimentary spa heating!
4 bedrooms, 6 beds
11–16 Aug
5.0 out of 5 average rating, 10 reviews
Superhost
Villa in Clermont
10BR Themed Villa w/ Pool, Theater & Game Room
10 bedrooms, 14 beds
9–14 Aug
New place to stay
Guest favourite
Home in Kissimmee
Magic Palms Villa
6 bedrooms, 9 beds
13–18 Aug
5.0 out of 5 average rating, 6 reviews