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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
21–26 Sept
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4.99 out of 5 average rating, 199 reviews
Flat in Winter Garden
Studio Apt close to Downtown & Bike Trail, Apt #3
1 bedroom, 1 king bed
14–19 Sept
Home in Orlando
Luxury 2BR Home | Private Patio & Stylish Stay
2 bedrooms, 2 king beds
25–30 Sept
New place to stay
Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
3 bedrooms, 3 queen beds
4–9 Oct
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds
20–25 Sept
4.92 out of 5 average rating, 97 reviews
Guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds
24–29 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds
2–7 Oct
4.94 out of 5 average rating, 35 reviews
Top guest favourite
Home in Clermont
Lake Front Home with private Dock on Lake Louisa
3 bedrooms, 4 beds
2–7 Oct
4.94 out of 5 average rating, 228 reviews
Superhost
Home in Clermont
Lake Louisa Retreat - Your Clermont Retreat.
4 bedrooms, 5 beds
1–6 Oct
Superhost
Home in Kissimmee
Private Pool • No Resort Fee | 10 Min to Disney
4 bedrooms, 5 beds
8–13 Oct
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Kissimmee
NEW Lois Ann's Disney Landing 4 miles to entrance!
3 bedrooms, 4 beds
1–6 Nov
5.0 out of 5 average rating, 3 reviews
Room in Winter Garden
J&K Accommodation
4 beds
14–19 Sept
New place to stay
Top guest favourite
Flat in Orlando
Spacious 2BR Oasis, Sleeps 8 Near Orlando Parks
2 bedrooms, 3 beds
19–24 Sept
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Kissimmee
Comfy Villa W/ Pool & FREE BBQ | Near Disney
4 bedrooms, 6 beds
5–10 Oct
New place to stay
Superhost
Home in Kissimmee
4BR house with private pool in Paradise Palms
4 bedrooms, 5 beds
14–19 Sept
New place to stay
Top guest favourite
Flat in Clermont
Downtown Clermont Scenic Retreat
2 bedrooms, 2 beds
15–20 Sept
5.0 out of 5 average rating, 14 reviews
Superhost
Home in Kissimmee
Family fun with private pool & bathtub near disney
3 bedrooms, 5 beds
22–27 Sept
New place to stay
Guest favourite
Townhouse in Clermont
5 Bd/ 4.5 Ba Windsor Cay (1276 Bp)
5 bedrooms, 8 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 11 reviews
Flat in Orlando
Enormous studio apartment in the heart of Orlando
1 bedroom, 1 queen bed
20–25 Sept
New place to stay