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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
17–22 Sept
,
4.89 out of 5 average rating, 169 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
14–19 Sept
New place to stay
Superhost
Home in Kissimmee
Comfy Villa W/ Pool & FREE BBQ | Near Disney
4 bedrooms, 6 beds
14–19 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
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds
14–19 Sept
4.96 out of 5 average rating, 49 reviews
Superhost
Home in Kissimmee
6 BD/ 6 BA/ Encore Resort at Reunion (480 Ld)
6 bedrooms, 7 beds
3–8 Oct
New place to stay
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
Guest favourite
Home in Kissimmee
Charming 3BR Home Near Disney with Comfort & Conve
3 bedrooms, 4 beds
19–24 Sept
5.0 out of 5 average rating, 7 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
Top guest favourite
Home in Kissimmee
Home, Private Pool, 10 min to Disney, 3 BR/2 Baths
3 bedrooms, 5 beds
1–6 Nov
4.98 out of 5 average rating, 46 reviews
Superhost
Home in Kissimmee
NEW Lois Ann's Disney Landing 4 miles to entrance!
3 bedrooms, 4 beds
1–6 Nov
New place to stay
Superhost
Home in Clermont
Lake Louisa Retreat - Your Clermont Retreat.
4 bedrooms, 5 beds
1–6 Oct
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
Apartment in Orlando
4114-306 Spacious 3bd condo at Vista Cay Resort
3 bedrooms, 7 beds
6–11 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
Superhost
Home in Kissimmee
NEW 2026 Themed 9BR| Racing Simulator |Solara
9 bedrooms, 13 beds
20–25 Sept
5.0 out of 5 average rating, 3 reviews