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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Guest house in Winter Garden
A place with a view
2 bedrooms, 3 beds, 1 private bathroom
3–8 Aug
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4.9 out of 5 average rating, 105 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
4.91 out of 5 average rating, 93 reviews, 3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
New place to stay, 10 bedrooms, 16 beds, 8 bathrooms
12–17 Oct
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5.0 out of 5 average rating, 7 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
11–16 Oct
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5.0 out of 5 average rating, 29 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
25–30 Aug
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
Guest favourite
Home in Clermont
Cozy Mod Escape | Sleeps 7 | "Oak Tree House"
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 5 beds, 2 bathrooms
21–26 Jul
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
5.0 out of 5 average rating, 26 reviews, 4 bedrooms, 6 beds, 3 bathrooms
2–7 Aug
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
4.96 out of 5 average rating, 48 reviews, 2 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Guest favourite
Townhouse in Kissimmee
4 Beds / 4.5 Baths / Magic Village Views (3085RW)
4.9 out of 5 average rating, 20 reviews, 4 bedrooms, 6 beds, 4.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 5 beds, 2 bathrooms
23–28 Jul
Superhost
Townhouse in Kissimmee
3 BD/ 2.5 BA/ Encantada Resort (3113 YL)
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Sept
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5.0 out of 5 average rating, 18 reviews, 5 bedrooms, 7 beds, 5.5 bathrooms
7–12 Aug
Flat in Orlando
Luxe King En-Suite• Universal/Epic 6 mins• Getaway
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Superhost
Home in Kissimmee
5 BD/ 4 BA/ Terra Verde (4669 GB)
5 bedrooms, 7 beds, 4 bathrooms
30 Jul – 4 Aug
Guest favourite
Home in Clermont
8 BD/ 6 BA / Windsor Cay (15989 CC)
5.0 out of 5 average rating, 7 reviews, 8 bedrooms, 12 beds, 6 bathrooms
2–7 Nov
Superhost
Townhouse in Davenport
Luxury Stay 5BR at Windsor Island - Near Disney
5 bedrooms, 7 beds, 5.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Townhouse in Orlando
Fun Family Townhome with Pool and Game Room!
5.0 out of 5 average rating, 7 reviews, 5 bedrooms, 9 beds, 5 bathrooms
23–28 Aug
Home in Kissimmee
Disney World Retreat Oasis & Private Pool
New place to stay, 5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug