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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
5–10 Aug
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4.97 out of 5 average rating, 351 reviews
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
5–10 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
5–10 Aug
5.0 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
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
Superhost
Flat in Orlando
Spacious2BR PetsFriendly Oasis Sleeps6, Pool & Gym
2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
New place to stay
Home in Orlando
Henry Balch Landing
4 bedrooms, 5 beds, 3 bathrooms
6–11 Aug
New place to stay
Home in Casselberry
Hilltop Haven – Peaceful Casselberry Getaway
3 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
New place to stay
Top guest favourite
Home in Longwood
Central Florida Pool Home
3 bedrooms, 2 beds, 2 bathrooms
6–11 Aug
4.96 out of 5 average rating, 55 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
New place to stay
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
Guest favourite
Home in Orlando
Magazine like huge home w/ pool city center/parks
7 bedrooms, 7 beds, 6.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 6 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
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 63 reviews
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds, 1 bathroom
19–24 Nov
4.98 out of 5 average rating, 45 reviews
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds, 2 bathrooms
2–7 Oct
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, 212 reviews
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
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds, 3.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 3 reviews