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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
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
Superhost
Home in Kissimmee
6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)
6 bedrooms, 8 beds, 4 bathrooms
21–26 Aug
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 Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
8–13 Aug
5.0 out of 5 average rating, 8 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
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
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
6–11 Sept
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
Home in Kissimmee
Spacious Condo with Balcony & Golf View at Reunion
3 bedrooms, 4 beds, 3 bathrooms
18–23 Jul
New place to stay
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Townhouse in Kissimmee
Disney Area Home • King & Mickey Room
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 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
3–8 Jul
4.96 out of 5 average rating, 46 reviews
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
Home in Kissimmee
NEW! Disney-Themed Escape | Private Pool | Villans
8 bedrooms, 13 beds, 6 bathrooms
6–11 Jul
New place to stay
Superhost
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 2.5 bathrooms
8–13 Aug
New place to stay
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
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
Superhost
Flat in Kissimmee
Walt Disney's Sketch Room! Resort Home near Disney
2 bedrooms, 3 beds, 2.5 bathrooms
1–6 Jul
New place to stay