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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
13–18 Sept
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5.0 out of 5 average rating, 4 reviews
Superhost
Home in Clermont
2026 Brand NEW 08 Bedrooms At Windsor Cay
8 bedrooms, 9 single beds, 6 bathrooms
1–6 Sept
New place to stay
Home in Clermont
Cozy Luxurious downtown lakeview home in Clermont
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Sept
New place to stay
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
Home in Kissimmee
Premium house, 4 bedrooms, sleeps 10, Kissimme
4 bedrooms, 8 beds, 3 bathrooms
1–6 Sept
New place to stay
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
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
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
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
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, 3 reviews
Superhost
Home in Clermont
Experience Our New 2026 10BR Home at Windsor Cay
10 bedrooms, 12 beds, 8 bathrooms
13–18 Sept
Superhost
Home in Clermont
10 Bd/ 8 Ba/ Windsor Cay (1031 Cr)
10 bedrooms, 15 beds, 8 bathrooms
7–12 Sept
Superhost
Home in Kissimmee
6 Bd/ 5 Ba/ Solara Resort (9038 Sr)
6 bedrooms, 11 beds, 5 bathrooms
6–11 Sept
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, 56 reviews
Guest favourite
Home in Clermont
Stunning 5B/4.5B, Heated Pool & BBQ
5 bedrooms, 7 beds, 4.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Orlando
5 Min- Epic Universe+KingBed+Disney
3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Kissimmee
Golden Haven | 5BR | Pool | 12 Min to Disney
5 bedrooms, 7 beds, 4.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Clermont
Downtown Clermont Scenic Retreat
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 14 reviews
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds, 2 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 3 reviews