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Search results; Over 1,000 homes in Winter Garden

Superhost
Home in Winter Garden
Downtown Winter Garden Luxury Retreat (NO Parties)
3 bedrooms, 3 beds, 1 private bathroom
7–12 Sept
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4.9 out of 5 average rating, 29 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.92 out of 5 average rating, 95 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
4.9 out of 5 average rating, 58 reviews
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
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 12 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
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
Superhost
Home in Montverde
3BD Montverde Lakeview Escape Near Orlando
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
New place to stay
Guest favourite
Flat in Clermont
Modern & Cozy Studio-Apartment
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 11 reviews
Superhost
Home in Kissimmee
Luxury Villa /Movie Theater/Pool Heater/
3 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 106 reviews
Guest favourite
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
15–20 Mar
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom, 1 king bed, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 46 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
Top guest favourite
Flat in Orlando
Modern 2BR Escape | King Bed • Pets • Epic U10 min
2 bedrooms, 3 beds, 2 bathrooms
2–7 Sept
5.0 out of 5 average rating, 44 reviews
Rooms in Apopka
Spacious close to everything Orlando has to offer
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
New place to stay
Top guest favourite
Guest house in Orlando
1924 Spanish Carriage House Lower
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 149 reviews
Superhost
Room in Winter Garden
Haven 15 minutes from Disney
1 bed, 1 bathroom
2–7 Sept
5.0 out of 5 average rating, 4 reviews
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