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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
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
Home in Kissimmee
Spacious Condo with Balcony & Golf View at Reunion
3 bedrooms, 4 beds, 3 bathrooms
18–23 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
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
Home in Davenport
Pelicans Landing
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
New place to stay
Superhost
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 2.5 bathrooms
3–8 Jul
New place to stay
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
Superhost
Townhouse in Clermont
Private Pool, BBQ | Steps to Clubhouse
3 bedrooms, 5 beds, 3 bathrooms
5–10 Aug
New place to stay
Superhost
Townhouse in Clermont
Brand 2026 NEW 05 Bdrms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
17–22 Aug
New place to stay
Superhost
Apartment in Davenport
2BR Resort Condo Near Disney – Family Ready
2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 3 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
NEW! Disney-Themed Escape | Private Pool | Villans
8 bedrooms, 13 beds, 6 bathrooms
6–11 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
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
Superhost
Townhouse in Orlando
Fun Family Townhome with Pool and Game Room!
5 bedrooms, 9 beds, 5 bathrooms
11–16 Jul
New place to stay
Top guest favourite
Villa in Clermont
Villa for 5 - Mins to Mickey, Golf, Pickleball, DT
2 bedrooms, 4 beds, 2 bathrooms
1–6 Jul
4.96 out of 5 average rating, 45 reviews
Top guest favourite
Townhouse in Kissimmee
NEW! Disney 15 Min • Kissimmee 3BR Lucaya Resort
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 8 reviews