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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Cottage in Winter Park
Winter Park Pearl 6 min drive to historic Park Ave
3 bedrooms, 3 beds, 1.5 private bathrooms
6–11 Aug
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4.95 out of 5 average rating, 465 reviews
Superhost
Home in Winter Park
Cute bungalow minutes walk from Park Ave.
2 bedrooms, 2 queen beds, 2 bathrooms
7–13 Nov
4.96 out of 5 average rating, 27 reviews
Guest favourite
Flat in Winter Park
The Grove
1 bedroom, 1 queen bed, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 7 reviews
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
6–11 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Winter Park
Stylish 2BR Near Park Ave & Rollins College
2 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
8–15 Aug
5.0 out of 5 average rating, 24 reviews
Home in Casselberry
Hilltop Haven – Peaceful Casselberry Getaway
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
New place to stay
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds, 2.5 bathrooms
15–20 Aug
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, 64 reviews
Top guest favourite
Treehouse in Orlando
Brand New Stylish & Unique Tree House!
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 77 reviews
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Guest suite in Orlando
~Chic Oasis • 6-Guest Suite • Pool Heat • Near All
2 bedrooms, 3 beds, 1 bathroom
10–15 Oct
4.98 out of 5 average rating, 444 reviews
Apartment in Casselberry
Cozy Private Apartment in Casselberry
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
New place to stay
Home in Orlando
Walk to Epic Universe | New! 3BR/3.5BA | Vista cay
3 bedrooms, 5 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Guest house in Orlando
Guest Home-Orlando Airport and Disney-Free Parking
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 52 reviews
Top guest favourite
Home in Longwood
Central Florida Pool Home
3 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
4.96 out of 5 average rating, 55 reviews
Superhost
Flat in Orlando
New luxury 3BD in Vista Cay · 5 min Epic Universe
3 bedrooms, 6 beds, 2 bathrooms
21–26 Aug
New place to stay
Top guest favourite
Guest house in Orlando
Modern 1950s Studio • Near Downtown & Theme Parks
1 bedroom, 1 queen bed, 1 bathroom
10–15 Aug
4.97 out of 5 average rating, 177 reviews
Hotel room in Orlando
From Sunrise Swims to Theme Park Thrills
1 bedroom, 2 queen beds, 1 bathroom
6–11 Aug
New place to stay