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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
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4.89 out of 5 average rating, 169 reviews
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5.0 out of 5 average rating, 7 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
21–26 Sept
Top guest favourite
Flat in Windermere
Relaxing 2BR Lakeview Retreat Close to Attractions
4.99 out of 5 average rating, 116 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Oct
Top guest favourite
Townhouse in Kissimmee
3 BD/ 3 BA/ The Hub At Westside (3349 TT)
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 5 beds, 3 bathrooms
13–18 Aug
Superhost
Home in Kissimmee
Beautiful 4 Bedroom Villa – Near Disney Parks
4 bedrooms, 6 beds, 4.5 bathrooms
18–23 Jul
Superhost
Home in Kissimmee
6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)
6 bedrooms, 8 beds, 4 bathrooms
1–6 Aug
Top guest favourite
Home in Clermont
Lux 6 bed with Pool/SPA
5.0 out of 5 average rating, 7 reviews, 6 bedrooms, 10 beds, 4 bathrooms
19–24 Jul
Superhost
Home in Clermont
Family pool home w/ game room near Disney
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5.0 out of 5 average rating, 18 reviews, 5 bedrooms, 7 beds, 5.5 bathrooms
26–31 Jul
Home in Kissimmee
10 minutes from Disney! Cozy Townhouse + Jacuzzi
New place to stay, 2 bedrooms, 4 beds, 2.5 bathrooms
3–8 Aug
Flat in Orlando
Luxe King En-Suite• Universal/Epic 6 mins• Getaway
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Guest favourite
Townhouse in Kissimmee
NEW 05 Bedrooms at Windsor Westside
5.0 out of 5 average rating, 15 reviews, 5 bedrooms, 9 beds, 4.5 bathrooms
21–26 Aug
Guest favourite
Townhouse in Kissimmee
4 Beds / 4.5 Baths / Magic Village Views (3085RW)
4.9 out of 5 average rating, 20 reviews, 4 bedrooms, 6 beds, 4.5 bathrooms
29 Aug – 3 Sept
Superhost
Townhouse in Kissimmee
3 BD/ 2.5 BA/ Encantada Resort (3113 YL)
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
3–8 Aug
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
4.98 out of 5 average rating, 83 reviews, 3 bedrooms, 4 beds, 3 bathrooms
8–13 Aug
Superhost
Home in Kissimmee
Greek Villa w/ Sunny Pool just 20 Min to Disney
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
4.99 out of 5 average rating, 78 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Superhost
Home in Clermont
Family Fun House at Windsor Cay
New place to stay, 5 bedrooms, 7 beds, 4.5 bathrooms
26–31 Jul