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
,
4.91 out of 5 average rating, 223 reviews
Top guest favourite
Flat in Clermont
Downtown Clermont Scenic Retreat
2 bedrooms, 2 beds
1–6 Jul
5.0 out of 5 average rating, 13 reviews
Home in Kissimmee
Spacious Condo with Balcony & Golf View at Reunion
3 bedrooms, 4 beds
18–23 Jul
New place to stay
Top guest favourite
Flat in Windermere
Relaxing 2BR Lakeview Retreat Close to Attractions
2 bedrooms, 3 beds
13–18 Jul
4.99 out of 5 average rating, 116 reviews
Superhost
Flat in Orlando
Golf Course View Spacious 2BR Condo
2 bedrooms, 2 beds
2–7 Jul
New place to stay
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds
25–30 Aug
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Clermont
2026 NEW Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 8 beds
5–10 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Room in Winter Garden
Haven 15 minutes from Disney
1 bed
1–6 Jul
5.0 out of 5 average rating, 4 reviews
Home in Davenport
Pelicans Landing
3 bedrooms, 4 beds
5–10 Jul
New place to stay
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds
12–17 Jul
5.0 out of 5 average rating, 23 reviews
Home in Kissimmee
Oversized Spa | Arcade Room | Kids Bedrooms | 030
6 bedrooms, 10 beds
5–10 Jul
4.83 out of 5 average rating, 6 reviews
Superhost
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds
3–8 Jul
New place to stay
Guest favourite
Home in Clermont
Brand 2026 Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 5 reviews
Villa in Orlando
Charming Orlando Villa with Pool & Family Fun
4 bedrooms, 6 beds
20–25 Jul
New place to stay
Guest favourite
Townhouse in Clermont
Spacious 3-bedroom, 3 baths condo near Disney
3 bedrooms, 4 beds
13–18 Jul
4.91 out of 5 average rating, 34 reviews
Superhost
Home in Kissimmee
6 BD/ 5.5 BA/ Solara Resort (1781 SP)
6 bedrooms, 8 beds
5–10 Jul
New place to stay
Guest favourite
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
7 bedrooms, 10 beds
25–30 Oct
5.0 out of 5 average rating, 5 reviews
Home in Kissimmee
NEW! Disney-Themed Escape | Private Pool | Villans
8 bedrooms, 13 beds
6–11 Jul
New place to stay
Superhost
Townhouse in Clermont
Private Pool, BBQ | Steps to Clubhouse
3 bedrooms, 5 beds
5–10 Aug
New place to stay