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Search results; Over 1,000 homes in Winter Garden

Guest favourite
Guest suite in Winter Garden
Designer Guest Suite Near Disney/Universal/DT
1 bedroom, 3 beds, 1 private bathroom
13–18 Aug
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4.84 out of 5 average rating, 413 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
4.91 out of 5 average rating, 93 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
4–9 Aug
New place to stay
Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
3 bedrooms, 3 queen beds, 2.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 81 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
New place to stay
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds, 3.5 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
8–13 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds, 5.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 21 reviews
Superhost
Home in Clermont
Pool, hot tub & arcade - 19 mins to Disney
4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds, 2 bathrooms
4–9 Aug
4.96 out of 5 average rating, 49 reviews
Superhost
Flat in Orlando
New luxury 3BD in Vista Cay · 5 min Epic Universe
3 bedrooms, 6 beds, 2 bathrooms
21–26 Aug
New place to stay
Home in Kissimmee
Modern Disney Villa • 7BR • Private Pool
7 bedrooms, 9 beds, 6.5 bathrooms
4–9 Aug
New place to stay
Superhost
Home in Four Corners
7 Bd/ 5.5 Ba/ Windsor Cay (1036 Bp)
7 bedrooms, 10 beds, 5.5 bathrooms
23–28 Aug
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
4–9 Aug
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Kissimmee
Amazing 03 Bedrooms/ 03 Baths / Sleeps 08
3 bedrooms, 5 beds, 3 bathrooms
8–13 Sept
4.97 out of 5 average rating, 37 reviews
Superhost
Townhouse in Clermont
5 Bd/ 4.5 Ba/ Windsor Cay (1252 Bi)
5 bedrooms, 9 beds, 4.5 bathrooms
16–21 Aug
New place to stay
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
28 Aug – 2 Sept