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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Home in Winter Garden
Downtown Winter Garden, Florida
2 bedrooms, 2 beds, 1 private bathroom
1–6 Sept
,
4.99 out of 5 average rating, 159 reviews
Superhost
Home in Montverde
3BD Montverde Lakeview Escape Near Orlando
3 bedrooms, 3 beds
20–25 Aug
New place to stay
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed
20–25 Aug
Superhost
Home in Clermont
2026 Brand NEW 08 Bedrooms At Windsor Cay
8 bedrooms, 9 single beds
13–18 Sept
New place to stay
Guest favourite
Townhouse in Kissimmee
3 Bd/ 2.5 Ba/ Encantada Resort (3113 Yl)
3 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds
20–25 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds
25–30 Aug
5.0 out of 5 average rating, 12 reviews
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds
21–26 Aug
4.9 out of 5 average rating, 58 reviews
Top guest favourite
Flat in Apopka
The little Manatee Home - Lake & Wildlife Retreat
1 bedroom, 2 beds
24–29 Aug
4.98 out of 5 average rating, 66 reviews
Superhost
Home in Kissimmee
Disney Oasis Bungalow with Palm-lined relaxation!
2 bedrooms, 4 beds
23–28 Aug
New place to stay
Superhost
Home in Clermont
Experience Our New 2026 10BR Home at Windsor Cay
10 bedrooms, 12 beds
13–18 Sept
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds
23–28 Aug
5.0 out of 5 average rating, 106 reviews
Guest favourite
Home in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds
3–8 Sept
5.0 out of 5 average rating, 21 reviews
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds
31 Oct – 5 Nov
New place to stay
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds
23–28 Nov
4.97 out of 5 average rating, 33 reviews
Superhost
Apartment in Kissimmee
Neverland Hideaway At Caribe Cove
2 bedrooms, 5 beds
21–26 Aug
New place to stay
Townhouse in Kissimmee
Disney Retreat w/ Private Pool & Resort Access
5 bedrooms, 7 beds
23–28 Aug
New place to stay