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Search results; Over 1,000 homes in Winter Garden

Guest favourite
Home in Winter Garden
Cozy Winter Garden Home 20 MINUTES FROM DISNEY
1 bedroom, 1 bed, 1 private bathroom
21–26 Sept
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4.92 out of 5 average rating, 225 reviews
Flat in Winter Garden
Studio Apt close to Downtown & Bike Trail, Apt #3
1 bedroom, 1 king bed
11–16 Sept
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds
11–16 Sept
5.0 out of 5 average rating, 12 reviews
Superhost
Home in Montverde
3BD Montverde Lakeview Escape Near Orlando
3 bedrooms, 3 beds
11–16 Sept
New place to stay
Top guest favourite
Home in Kissimmee
Amazing 3Bdrms/2,5bath At Encantada
3 bedrooms, 5 beds
12–17 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds
13–18 Sept
4.94 out of 5 average rating, 35 reviews
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds
11–16 Sept
5.0 out of 5 average rating, 28 reviews
Guest favourite
Room in Winter Garden
Haven 15 minutes from Disney
1 bed
12–17 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
6 bedrooms, 9 beds
14–19 Sept
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds
11–16 Sept
4.96 out of 5 average rating, 49 reviews
Superhost
Apartment in Kissimmee
Neverland Hideaway At Caribe Cove
2 bedrooms, 5 beds
14–19 Sept
Top guest favourite
Flat in Clermont
Downtown Clermont Scenic Retreat
2 bedrooms, 2 beds
12–17 Sept
5.0 out of 5 average rating, 14 reviews
Superhost
Rooms in Oakland
Oakland Trails
2 bedrooms, 2 queen beds
22–27 Sept
5.0 out of 5 average rating, 4 reviews
Featured hotel
Hotel in Kissimmee
Family double queen room
1 bedroom, 2 queen beds
11–16 Sept
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds
15–20 Sept
4.9 out of 5 average rating, 58 reviews
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds
23–28 Sept
5.0 out of 5 average rating, 106 reviews
Superhost
Home in Clermont
2026 NEW Themed 5-Bedroom Home at Windsor Cay
5 bedrooms, 5 beds
29 Nov – 4 Dec
Guest favourite
Apartment in Orlando
Vista Cay Lakeview Chic, Next To Epic And Occc
2 bedrooms, 3 beds
13–18 Sept
5.0 out of 5 average rating, 71 reviews
Superhost
Home in Kissimmee
Comfy Villa W/ Pool & FREE BBQ | Near Disney
4 bedrooms, 6 beds
13–18 Sept
New place to stay