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Search results; Over 1,000 homes in Winter Garden

Cottage in Winter Garden
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
2 bedrooms, 3 beds, 1 private bath
Aug 19 – 24
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4.88 out of 5 average rating, 123 reviews
Superhost
Home in Gotha
Stylish Home • Sleeps 8 • Near Disney & Universal
3 bedrooms, 6 beds, 2.5 baths
Aug 16 – 21
New place to stay
Top guest favorite
Home in Clermont
Cozy Clermont Retreat
6 bedrooms, 9 beds, 4 baths
Aug 21 – 26
4.98 out of 5 average rating, 51 reviews
Top guest favorite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 baths
Aug 12 – 17
5.0 out of 5 average rating, 12 reviews
Home in Kissimmee
Kings Castle Retreat
5 bedrooms, 9 beds, 5 baths
Aug 16 – 21
New place to stay
Top guest favorite
Apartment in Apopka
The little Manatee Home - Lake & Wildlife Retreat
1 bedroom, 2 beds, 1 bath
Aug 19 – 24
4.98 out of 5 average rating, 65 reviews
Apartment in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bath
Aug 12 – 17
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 baths
Aug 16 – 21
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Home in Kissimmee
Stylish Disney Retreat | 15 Mins to Disney
3 bedrooms, 4 beds, 3 baths
Aug 29 – Sep 3
5.0 out of 5 average rating, 5 reviews
Top guest favorite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 baths
Aug 16 – 21
5.0 out of 5 average rating, 28 reviews
Top guest favorite
Home in Kissimmee
Home, Private Pool, 10 min to Disney, 3 BR/2 Baths
3 bedrooms, 5 beds, 2 baths
Sep 28 – Oct 3
4.98 out of 5 average rating, 40 reviews
Guest favorite
Townhouse in Kissimmee
Elegant townhouse w/ pool & resort access
5 bedrooms, 8 beds, 5 baths
Aug 19 – 24
5.0 out of 5 average rating, 13 reviews
Top guest favorite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bath
Aug 16 – 21
4.9 out of 5 average rating, 58 reviews
Top guest favorite
Home in Davenport
Home Away from Home + 2 suites
5 bedrooms, 6 beds, 3 baths
Aug 18 – 23
5.0 out of 5 average rating, 9 reviews
Guest favorite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 baths
Aug 14 – 19
5.0 out of 5 average rating, 104 reviews
Guest favorite
Townhouse in Kissimmee
3 Bd/ 2.5 Ba/ Encantada Resort (3113 Yl)
3 bedrooms, 4 beds, 2.5 baths
Aug 24 – 29
5.0 out of 5 average rating, 6 reviews
Guest favorite
Home in Kissimmee
2026 NEW 06 Bedrooms at Solara Resort/Private Pool
6 bedrooms, 9 beds, 4.5 baths
Oct 4 – 9
5.0 out of 5 average rating, 16 reviews
Top guest favorite
Townhouse in Kissimmee
Near Disney Oasis | Pool | Free BBQ | Pet-Friendly
4 bedrooms, 8 beds, 3 baths
Aug 12 – 17
5.0 out of 5 average rating, 47 reviews
Guest favorite
Townhouse in Kissimmee
3 Bd/ 3 Ba/ The Hub At Westside (3349 Tt)
3 bedrooms, 5 beds, 3 baths
Aug 22 – 27
4.88 out of 5 average rating, 8 reviews