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Search results; Over 1,000 homes in Winter Park

Guest favourite
Bungalow in Winter Park
Cozy 2/2 Home - Downtown Winterpark/Orlando
2 bedrooms, 2 beds, 2 private bathrooms
17–22 Aug
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4.97 out of 5 average rating, 351 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Winter Park
Luxurious 2BR Near Park Ave & Rollins College
2 bedrooms, 4 beds, 2 bathrooms
2–7 Sept
5.0 out of 5 average rating, 28 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, 10 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
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
Home in Orlando
Magazine like huge home w/ pool city center/parks
7 bedrooms, 7 beds, 6.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Guest house in Orlando
Modern 1950s Studio • Near Downtown & Theme Parks
1 bedroom, 1 queen bed, 1 bathroom
13–18 Aug
4.97 out of 5 average rating, 178 reviews
Home in Orlando
The Lullaby Retreat | Wekiva & Winter Park
2 bedrooms, 2 beds, 1 bathroom
13–18 Aug
New place to stay
Superhost
Flat in Orlando
Spacious2BR PetsFriendly Oasis Sleeps 6, Pool&Gym
2 bedrooms, 3 beds, 2 bathrooms
14–19 Aug
New place to stay
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
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds, 1 bathroom
12–17 Aug
5.0 out of 5 average rating, 213 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
Top guest favourite
Flat in Orlando
Spacious 2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 39 reviews
Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds, 2.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds, 1 bathroom
22–27 Nov
4.98 out of 5 average rating, 46 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Orlando
Massive Corner 3 Bedroom 2 Bath
3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 5 reviews