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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 Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds
5–10 Aug
4.91 out of 5 average rating, 93 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed
1–6 Aug
New place to stay
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds
9–14 Nov
5.0 out of 5 average rating, 3 reviews
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
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
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds
10–15 Aug
New place to stay
Top guest favourite
Townhouse in Kissimmee
3 BD/ 2.5 BA/ Encantada Resort (3113 YL)
3 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Kissimmee
Amazing 03 Bedrooms/ 03 Baths / Sleeps 08
3 bedrooms, 5 beds
25–30 Aug
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Home in Clermont
2026 Cozy Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds
22–27 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds
1–6 Aug
4.89 out of 5 average rating, 56 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds
6–11 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds
1–6 Aug
4.96 out of 5 average rating, 49 reviews
Top guest favourite
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 Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds
28 Aug – 2 Sept
Superhost
Home in Kissimmee
The Most Fun House, Tons of Room and a Huge Pool!
12 bedrooms, 24 beds
5–10 Aug
New place to stay
Superhost
Home in Clermont
Family Fun House at Windsor Cay
5 bedrooms, 7 beds
2–7 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds
23–28 Aug
4.98 out of 5 average rating, 86 reviews
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds
13–18 Sept
New place to stay