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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Cottage in Winter Garden
The Heart of Winter Garden: Walk to shops & dining
2 bedrooms, 2 beds, 1 private bathroom
9–14 Sept
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4.99 out of 5 average rating, 197 reviews
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom, 1 king bed, 1 bathroom
1–6 Aug
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Room in Ocoee
Updated 1 bedroom/ 1 bathroom
1 queen bed, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 30 reviews
Room in St. Cloud
Peaceful private room
1 bed, WC
1–6 Jan
New place to stay
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
4.89 out of 5 average rating, 55 reviews
Top guest favourite
Flat in Ocoee
Quiet Comfy Apartment Orlando Area
1 bedroom, 1 queen bed, 1 bathroom
11–16 Aug
4.83 out of 5 average rating, 113 reviews
Superhost
Townhouse in Kissimmee
3 BD/ 2.5 BA/ Encantada Resort (3113 YL)
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Apopka
The little Manatee Home - Lake & Wildlife Retreat
1 bedroom, 2 beds, 1 bathroom
25–30 Aug
4.98 out of 5 average rating, 60 reviews
Superhost
Room in Winter Garden
Haven 15 minutes from Disney
1 bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in Winter Park
The Grove
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Kissimmee
Beautiful 4 Bedroom Villa – Near Disney Parks
4 bedrooms, 6 beds, 4.5 bathrooms
8–13 Aug
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds, 8 bathrooms
12–17 Oct
New place to stay
Top guest favourite
Guest suite in Clermont
Traveling med staff,pro athletes & remote worker
1 bedroom, 2 single beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 66 reviews
Home in Orlando
Walk to Epic Universe | New! 3BR/3.5BA | Vista cay
3 bedrooms, 5 beds, 3.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Orlando
Retreat Luxury Fully Renovated 2026 / Free Shuttle
1 bedroom, 2 queen beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Flat in Kissimmee
3176-205 Resort Pool Condo Apt near Disney
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Camper van/Motorhome in Clermont
Luxurious 42 foot Class A RV on 5 forested acres
2 bedrooms, 1 king bed, 1 bathroom
7–12 Feb
5.0 out of 5 average rating, 45 reviews
Room in Orlando
Disney Shuttle Studio | Resort Pool & Parking
1 king bed, 1 bathroom
1–6 Aug
Guest favourite
Flat in Orlando
Luxury King, Close to Parks, PetFriendly,Pool, Gym
1 bedroom, 2 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 9 reviews