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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, 419 reviews
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, 24 reviews
Guest favourite
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
7 bedrooms, 10 beds, 5.5 bathrooms
6–11 Mar
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 28 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 New 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
3–8 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Townhouse in Clermont
Private Pool, BBQ | Steps to Clubhouse
3 bedrooms, 5 beds, 3 bathrooms
7–12 Aug
New place to stay
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
Guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
16–21 Jul
5.0 out of 5 average rating, 11 reviews
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, 91 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
Superhost
Cottage in Kissimmee
Beauty and the Beast
2 bedrooms, 3 beds, 2 bathrooms
15–20 Jul
New place to stay
Guest favourite
Townhouse in Kissimmee
NEW 05 Bedrooms at Windsor Westside
5 bedrooms, 9 beds, 4.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Villa in Clermont
Villa for 5 - Visiting family, Golfing, Downtown
2 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
4.96 out of 5 average rating, 47 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, 31 reviews
Superhost
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 2.5 bathrooms
8–13 Aug
New place to stay
Home in Kissimmee
Santosh Cove Retreat
4 bedrooms, 5 beds, 3.5 bathrooms
4–9 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Townhouse in Kissimmee
Magic Village 4 Suites w/ Jacuzzi - 7493
4 bedrooms, 7 beds, 4.5 bathrooms
6–11 Jul
4.88 out of 5 average rating, 82 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