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Search results; Over 1,000 homes in Winter Garden

Hotel in Winter Garden
Rare Gem! Outdoor Pool, Kitchenette, Pets Allowed!
1 bedroom, 2 beds, 1 private bathroom
7–12 Sept
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5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Orlando
Orlando Bliss near Disney
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 14 reviews
Home in Kissimmee
Premium house, 4 bedrooms, sleeps 10, Kissimme
4 bedrooms, 8 beds, 3 bathrooms
1–6 Sept
New place to stay
Home in Clermont
25 miles to Disney Contry side house
4 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
New place to stay
Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
3 bedrooms, 3 queen beds, 2.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 85 reviews
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Superhost
Rooms in Oakland
Oakland Trails
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 4 reviews
Townhouse in Kissimmee
Magical Family Retreat 4B, 3.5B, Spa, 4M Disney!
4 bedrooms, 8 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Apartment in Kissimmee
Neverland Hideaway At Caribe Cove
2 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
New place to stay
Superhost
Home in Four Corners
8BR house with private pool and game room
8 bedrooms, 8 beds, 6 bathrooms
1–6 Sept
New place to stay
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Davenport
3BR Luxury Disney Escape | Hot Tub & 2 King Suites
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Sept
New place to stay
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds, 4.5 bathrooms
6–11 Apr
Top guest favourite
Apartment in Kissimmee
Renovated Family Condo • Disney • Free Parking
2 bedrooms, 4 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 57 reviews
Superhost
Townhouse in Kissimmee
4 Bd/ 3 Ba/ Lucaya Village (8-101)
4 bedrooms, 7 beds, 3 bathrooms
6–11 Sept
Superhost
Flat in Orlando
Kids friendly 3 bedroom Condo - Tourist location
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
New place to stay
Guest favourite
Townhouse in Kissimmee
4 Bd/ 3 Ba/ West Lucaya (8984 Sp)
4 bedrooms, 6 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 8 reviews