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Search results; Over 1,000 homes in Winter Garden

Guest favourite
Flat in Winter Garden
Stay A While
1 bedroom, 3 beds, 1 private bathroom
5–10 Aug
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4.89 out of 5 average rating, 169 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
21–26 Jul
New place to stay
Superhost
Room in Winter Garden
Haven 15 minutes from Disney
1 bed, 1 bathroom
22–27 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom, 1 king bed, 1 bathroom
28 Jul – 2 Aug
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Flat in Orlando
New 1 Bedroom Suite with full kitchen, Bathroom #1
1 bedroom, 2 beds, 1 bathroom
22–27 Jul
4.96 out of 5 average rating, 24 reviews
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
Townhouse in Clermont
Home for 2! Heated Pool, Private Patio, Queen Bed
1 bedroom, 1 queen bed, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Flat in Clermont
Modern & Cozy Studio-Apartment
1 bedroom, 2 beds, 1 bathroom
21–26 Jul
5.0 out of 5 average rating, 10 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
Top guest favourite
Flat in Kissimmee
Amazing 03 Bedrooms/ 03 Baths / Sleeps 08
3 bedrooms, 5 beds, 3 bathrooms
25–30 Aug
4.97 out of 5 average rating, 36 reviews
Superhost
Room in Davenport
Suite in Villa|Private Bath|Pool&Spa|Disney
1 queen bed, 1 bathroom
21–26 Jul
New place to stay
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
Apartment in Kissimmee
New! Seven Eagles Hideaway at Reunion Resort
1 bedroom, 1 king bed, 1 bathroom
5–10 Aug
5.0 out of 5 average rating, 18 reviews
Superhost
Townhouse in Davenport
3BD/2.5BATH Family Getaway in a Prime Location
3 bedrooms, 4 beds, 2.5 bathrooms
27 Jul – 1 Aug
New place to stay
Top guest favourite
Townhouse in Kissimmee
3 BD/ 3 BA/ The Hub At Westside (3349 TT)
3 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
4.89 out of 5 average rating, 55 reviews
Home in Kissimmee
Disney World Retreat Oasis & Private Pool
5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug
New place to stay
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom, 1 queen bed, 1 bathroom
23–28 Jul
5.0 out of 5 average rating, 134 reviews