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Search results; Over 1,000 homes in Winter Garden

Guest favourite
Guest suite in Winter Garden
Private In-Law Suite Near Disney/Universal/DT
1 bedroom, 1 bed, 1 private bathroom
14–19 Jul
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4.84 out of 5 average rating, 417 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
Villa for 5 - Visiting family, Golfing, Downtown
2 bedrooms, 4 beds, 2 bathrooms
3–8 Jul
4.96 out of 5 average rating, 46 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
Villa in Orlando
Charming Orlando Villa with Pool & Family Fun
4 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
New place to stay
Superhost
Townhouse in Kissimmee
3 BD/ 3 BA/ The Hub At Westside (3349 TT)
3 bedrooms, 5 beds, 3 bathrooms
28 Jul – 2 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
6–11 Aug
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
8–13 Jul
5.0 out of 5 average rating, 23 reviews
Superhost
Home in Kissimmee
6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)
6 bedrooms, 8 beds, 4 bathrooms
9–14 Sept
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
26–31 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Clermont
Brand 2026 Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4 bathrooms
16–21 Nov
5.0 out of 5 average rating, 5 reviews
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Home in Kissimmee
Spacious Condo with Balcony & Golf View at Reunion
3 bedrooms, 4 beds, 3 bathrooms
18–23 Jul
New place to stay
Townhouse in Clermont
3 BR home with private pool and wifi
3 bedrooms, 3 beds, 3 bathrooms
29 Jul – 3 Aug
Superhost
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 2.5 bathrooms
8–13 Aug
New place to stay
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
4.91 out of 5 average rating, 90 reviews
Superhost
Townhouse in Kissimmee
5 BD/ 4 BA/ Story Lake (4810 ML)
5 bedrooms, 7 beds, 4 bathrooms
20–25 Jul
Superhost
Cottage in Kissimmee
Beauty and the Beast
2 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
New place to stay
Townhouse in Orlando
Sweet Orlando getaway Near Disney World/Universal.
3 bedrooms, 3 beds, 2.5 bathrooms
11–16 Jul
New place to stay