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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Home in Winter Garden
Downtown Bungalow with fire pit and putting green
2 bedrooms, 2 beds, 1 private bathroom
1–6 Sept
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4.97 out of 5 average rating, 132 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds
10–15 Aug
New place to stay
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds
5–10 Aug
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 14 reviews
Superhost
Home in Four Corners
7 Bd/ 5.5 Ba/ Windsor Cay (1036 Bp)
7 bedrooms, 10 beds
23–28 Aug
Guest favourite
Home in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds
21–26 Sept
5.0 out of 5 average rating, 21 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed
5–10 Aug
New place to stay
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds
9–14 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds
5–10 Aug
5.0 out of 5 average rating, 27 reviews
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds
17–22 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Kissimmee
6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)
6 bedrooms, 8 beds
10–15 Aug
Room in Ocoee
Bedroom and private bathroom
1 queen bed
8–13 Aug
New place to stay
Superhost
Townhouse in Clermont
5 BD/ 4.5 BA/ Windsor Cay (16218 CC)
5 bedrooms, 7 beds
18–23 Oct
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds
23–28 Aug
Superhost
Home in Clermont
Pool, hot tub & arcade - 19 mins to Disney
4 bedrooms, 5 beds
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Kissimmee
Amazing 03 Bedrooms/ 03 Baths / Sleeps 08
3 bedrooms, 5 beds
8–13 Sept
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds
23–28 Aug
4.98 out of 5 average rating, 86 reviews
Top guest favourite
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Flat in Orlando
New luxury 3BD in Vista Cay · 5 min Epic Universe
3 bedrooms, 6 beds
21–26 Aug
New place to stay