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Search results; Over 1,000 homes in Winter Garden

Guest favourite
Home in Winter Garden
Cozy Winter Garden Home 20 MINUTES FROM DISNEY
1 bedroom, 1 bed, 1 private bathroom
2–7 Aug
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4.91 out of 5 average rating, 223 reviews
Top guest favourite
Guest house in Winter Garden
A place with a view
2 bedrooms, 3 beds, 1 bathroom
1–6 Jul
4.9 out of 5 average rating, 103 reviews
Home in Kissimmee
Home Near Disney with pool, theater & games.
3 bedrooms, 5 beds, 1 bathroom
1–6 Jul
New place to stay
Home in Kissimmee
Spacious Condo with Balcony & Golf View at Reunion
3 bedrooms, 4 beds, 3 bathrooms
18–23 Jul
New place to stay
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Windermere
Relaxing 2BR Lakeview Retreat Close to Attractions
2 bedrooms, 3 beds, 1 bathroom
13–18 Jul
4.99 out of 5 average rating, 116 reviews
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Clermont
Brand 2026 Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Clermont
2026 NEW Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 8 beds, 4 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 5 reviews
Home in Davenport
Pelicans Landing
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
New place to stay
Home in Kissimmee
Oversized Spa | Arcade Room | Kids Bedrooms | 030
6 bedrooms, 10 beds, 6 bathrooms
5–10 Jul
4.83 out of 5 average rating, 6 reviews
Top guest favourite
Home in Kissimmee
Elegant 5B & 3B Private Pool Villa near Disney
5 bedrooms, 8 beds, 3 bathrooms
2–7 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Townhouse in Clermont
Spacious 3-bedroom, 3 baths condo near Disney
3 bedrooms, 4 beds, 3 bathrooms
13–18 Jul
4.91 out of 5 average rating, 34 reviews
Home in Kissimmee
Disney Theme 7 Bedroom Home, Pool, Spa, Game Room
7 bedrooms, 12 beds, 5 bathrooms
26–31 Jul
New place to stay
Guest favourite
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
7 bedrooms, 10 beds, 5.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 5 reviews
Superhost
Flat in Orlando
Golf Course View Spacious 2BR Condo
2 bedrooms, 2 beds, 2 bathrooms
2–7 Jul
New place to stay
Home in Kissimmee
Disney 15 Min! 4 BR Themed Home With Private Pool
4 bedrooms, 5 beds, 3 bathrooms
3–8 Jul
New place to stay
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5 bedrooms, 7 beds, 5.5 bathrooms
7–12 Jul
5.0 out of 5 average rating, 15 reviews
Superhost
Townhouse in Clermont
Brand 2026 NEW 05 Bdrms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
21–26 Sept
New place to stay