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Search results; Over 1,000 homes in Winter Garden

Superhost
Apartment in Winter Garden
Upstay Modern 2BR Condo Near Disney
2 bedrooms, 3 beds, 2 private bathrooms
21–26 Sept
,
4.85 out of 5 average rating, 34 reviews
Flat in Winter Garden
Studio Apt close to Downtown & Bike Trail, Apt #3
1 bedroom, 1 king bed, 1 bathroom
14–19 Sept
Home in Orlando
Luxury 2BR Home | Private Patio & Stylish Stay
2 bedrooms, 2 king beds, 1 bathroom
14–19 Sept
New place to stay
Superhost
Home in Kissimmee
Comfy Villa W/ Pool & FREE BBQ | Near Disney
4 bedrooms, 6 beds, 3 bathrooms
14–19 Sept
New place to stay
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
2–7 Oct
4.94 out of 5 average rating, 35 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 97 reviews
Superhost
Home in Clermont
Lake Louisa Retreat - Your Clermont Retreat.
4 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
Guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
24–29 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
3 bedrooms, 3 queen beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 89 reviews
Room in Winter Garden
J&K Accommodation
4 beds, 1 bathroom
14–19 Sept
New place to stay
Apartment in Kissimmee
Peaceful 3BR Condo Near Disney + Resort Amenities
3 bedrooms, 4 beds, 2 bathrooms
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, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Kissimmee
Amazing 3Bdrms/2,5bath At Encantada
3 bedrooms, 5 beds, 2.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds, 5.5 bathrooms
2–7 Nov
5.0 out of 5 average rating, 24 reviews
Superhost
Home in Kissimmee
NEW 2026 Themed 9BR| Racing Simulator |Solara
9 bedrooms, 13 beds, 6.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Kissimmee
Magical Stay Near Disney
4 bedrooms, 5 beds, 3 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Clermont
Lake Front Home with private Dock on Lake Louisa
3 bedrooms, 4 beds, 2 bathrooms
2–7 Oct
4.94 out of 5 average rating, 228 reviews
Superhost
Home in Kissimmee
4BR house with private pool in Paradise Palms
4 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
New place to stay
Superhost
Townhouse in Kissimmee
2688 Waterfront Townhouse w/ Hot Tub 3mi to Disney
3 bedrooms, 5 beds, 2.5 bathrooms
14–19 Sept
New place to stay