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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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4.92 out of 5 average rating, 224 reviews
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
30 Jul – 4 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Windermere
Relaxing 2BR Lakeview Retreat Close to Attractions
2 bedrooms, 3 beds, 1 bathroom
16–21 Jul
4.99 out of 5 average rating, 116 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
4.89 out of 5 average rating, 55 reviews
Superhost
Home in Clermont
Family pool home w/ game room near Disney
4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
23–28 Jul
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom, 1 king bed, 1 bathroom
21–26 Jul
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Townhouse in Kissimmee
3 BD/ 3 BA/ The Hub At Westside (3349 TT)
3 bedrooms, 5 beds, 3 bathrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds, 3 bathrooms
29 Jul – 3 Aug
4.98 out of 5 average rating, 83 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
31 Jul – 5 Aug
New place to stay
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
Flat in Orlando
Luxe King En-Suite• Universal/Epic 6 mins• Getaway
2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
New place to stay
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.91 out of 5 average rating, 92 reviews
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Guest favourite
Home in Clermont
8 BD/ 6 BA / Windsor Cay (15989 CC)
8 bedrooms, 12 beds, 6 bathrooms
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Superhost
Townhouse in Kissimmee
3 BD/ 2.5 BA/ Encantada Resort (3113 YL)
3 bedrooms, 4 beds, 2.5 bathrooms
3–8 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds, 8 bathrooms
15–20 Aug
New place to stay
Superhost
Home in Kissimmee
Disney 7 Min • Luxury 4 Suites • Jacuzzi • Arcade
4 bedrooms, 8 beds, 5 bathrooms
1–6 Aug
New place to stay
Superhost
Townhouse in Clermont
Brand 2026 NEW 05 Bdrms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 3 reviews