filters

Search results; Over 1,000 homes in Winter Garden

Guest favourite
Flat in Winter Garden
Stay A While
1 bedroom, 3 beds, 1 private bathroom
5–10 Aug
,
4.89 out of 5 average rating, 169 reviews
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
4.89 out of 5 average rating, 55 reviews
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds, 8 bathrooms
8–13 Sept
New place to stay
Superhost
Home in Clermont
2026 NEW! Stunning 09 Bedroom at Windsor Cay
9 bedrooms, 12 beds, 6 bathrooms
1–6 Aug
New place to stay
Top guest favourite
Home in Clermont
Lux 6 bed with Pool/SPA
6 bedrooms, 10 beds, 4 bathrooms
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Kissimmee
Beautiful 4 Bedroom Villa – Near Disney Parks
4 bedrooms, 6 beds, 4.5 bathrooms
18–23 Jul
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
23–28 Jul
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Townhouse in Kissimmee
3 BD/ 3 BA/ The Hub At Westside (3349 TT)
3 bedrooms, 5 beds, 3 bathrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5 bedrooms, 7 beds, 5.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 18 reviews
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
Superhost
Townhouse in Kissimmee
3 BD/ 2.5 BA/ Encantada Resort (3113 YL)
3 bedrooms, 4 beds, 2.5 bathrooms
3–8 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Townhouse in Kissimmee
4 Beds / 4.5 Baths / Magic Village Views (3085RW)
4 bedrooms, 6 beds, 4.5 bathrooms
16–21 Aug
4.9 out of 5 average rating, 20 reviews
Superhost
Cottage in Kissimmee
Beauty and the Beast
2 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 4 reviews
Home in Davenport
Davenport Disney Destination w/Pool
3 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 3 reviews
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Superhost
Home in Kissimmee
6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)
6 bedrooms, 8 beds, 4 bathrooms
9–14 Sept
Guest favourite
Home in Clermont
8 BD/ 6 BA / Windsor Cay (15989 CC)
8 bedrooms, 12 beds, 6 bathrooms
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
26–31 Jul
5.0 out of 5 average rating, 25 reviews