filters

Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Guest house in Winter Garden
A place with a view
2 bedrooms, 3 beds, 1 private bathroom
3–8 Aug
,
4.9 out of 5 average rating, 105 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
10–15 Aug
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
4.96 out of 5 average rating, 48 reviews, 2 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
New place to stay, 10 bedrooms, 16 beds, 8 bathrooms
8–13 Sept
Guest favourite
Home in Clermont
Lux 6 bed with Pool/SPA
5.0 out of 5 average rating, 8 reviews, 6 bedrooms, 10 beds, 4 bathrooms
19–24 Jul
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
5.0 out of 5 average rating, 26 reviews, 4 bedrooms, 6 beds, 3 bathrooms
2–7 Aug
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
7–12 Aug
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 4 bathrooms
19–24 Jul
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
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
Guest favourite
Villa in Clermont
Villa near Disney with complimentary spa heating!
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 6 beds, 2 bathrooms
28 Jul – 2 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
Top guest favourite
Flat in Kissimmee
Amazing 03 Bedrooms/ 03 Baths / Sleeps 08
4.97 out of 5 average rating, 36 reviews, 3 bedrooms, 5 beds, 3 bathrooms
25–30 Aug
Home in Kissimmee
Disney World Retreat Oasis & Private Pool
New place to stay, 5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug
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
1–6 Sept
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
4.98 out of 5 average rating, 48 reviews, 6 bedrooms, 9 beds, 4 bathrooms
26–31 Jul