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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, 198 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
New place to stay
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, 38 reviews
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
Room in Ocoee
Bedroom and private bathroom
1 queen bed, 1.5 bathrooms
7–12 Aug
New place to stay
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 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
Top guest favourite
Flat in Orlando
Modern Oasis | King Bed • Pool & Gym • Near Epic U
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 61 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
Top guest favourite
Flat in Orlando
New 1 Bedroom Suite with full kitchen, Bathroom #1
1 bedroom, 2 beds, 1 bathroom
1–6 Aug
4.96 out of 5 average rating, 24 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
Top guest favourite
Townhouse in Clermont
House for 2! Heated Pool, Private Patio, Queen Bed
1 bedroom, 1 queen bed, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 21 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, 61 reviews
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds, 8 bathrooms
31 Aug – 5 Sept
New place to stay
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
10–15 Aug
4.89 out of 5 average rating, 9 reviews
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
26–31 Aug
Superhost
Apartment in Kissimmee
9-201 Legacy Dunes, Heated Pool. Close to Disney
2 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
New place to stay
Top guest favourite
Flat in Winter Park
The Grove
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 5 reviews
Room in St. Cloud
Peaceful private room
1 bed, WC
1–6 Jan
New place to stay