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Search results; Over 1,000 homes in Winter Garden

Cottage in Winter Garden
16 Mi to Disney: Cottage w/ Deck in Winter Garden
1 bedroom, 2 beds, 1 bathroom
25–30 Aug
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4.83 out of 5 average rating, 59 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.91 out of 5 average rating, 94 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 58 reviews
Townhouse in Kissimmee
Magical Family Retreat 4B, 3.5B, Spa, 4M Disney!
4 bedrooms, 8 beds, 3.5 bathrooms
28 Aug – 2 Sept
New place to stay
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 105 reviews
Top guest favourite
Flat in Kissimmee
Vacation Condo with pool-20 Min from Disney
2 bedrooms, 5 beds, 2 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 8 reviews
Home in Kissimmee
Premium house, 4 bedrooms, sleeps 10, Kissimme
4 bedrooms, 8 beds, 3 bathrooms
24–29 Aug
New place to stay
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 3 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
13–18 Aug
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
23–28 Nov
5.0 out of 5 average rating, 30 reviews
Superhost
Guest house in Orlando
Guest Home| Orlando Airport & Florida Mall 15 min
1 bedroom, 2 beds, 1 bathroom
21–26 Aug
New place to stay
Guest favourite
Home in Clermont
2026 NEW Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 8 beds, 4 bathrooms
27 Jan – 1 Feb
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Orlando
Walk to Epic Universe | New! 3BR/3.5BA | Vista cay
3 bedrooms, 5 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 7 reviews
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds, 2 bathrooms
2–7 Oct
New place to stay
Guest favourite
Home in Davenport
The Ultimate Family Getaway Near Disney
3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Aug
4.94 out of 5 average rating, 18 reviews
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
4.98 out of 5 average rating, 86 reviews
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
4.96 out of 5 average rating, 49 reviews
Superhost
Guest house in Orlando
Modern Private Studio near Orlando attractions
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
New place to stay
Guest favourite
Townhouse in Kissimmee
3 Bd/ 2.5 Ba/ Encantada Resort (3113 Yl)
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 7 reviews