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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
4–9 Aug
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4.95 out of 5 average rating, 465 reviews
Guest favourite
Flat in Winter Park
The Grove
1 bedroom, 1 queen bed
24–29 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest suite in Orlando
A SUITE RETREAT with a Garden View in the City
1 bedroom, 1 queen bed
9–14 Aug
4.97 out of 5 average rating, 476 reviews
Top guest favourite
Home in Winter Park
Stylish 2BR Near Park Ave & Rollins College
2 bedrooms, 4 beds
22–27 Aug
5.0 out of 5 average rating, 26 reviews
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds
4–9 Aug
5.0 out of 5 average rating, 5 reviews
Home in Orlando
Henry Balch Landing
4 bedrooms, 5 beds
5–10 Aug
New place to stay
Top guest favourite
Guest house in Orlando
1924 Spanish Carriage House Lower
1 bedroom, 2 beds
4–9 Aug
4.98 out of 5 average rating, 146 reviews
Flat in Orlando
Elevated Living Apt
1 bedroom, 1 bed
4–9 Aug
Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed
6–11 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Room in Orlando
Renovated Centrally Located Double Room
1 queen bed
4–9 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Orlando
Sunny Oasis: Downtown Orlando with Suburban feel
2 bedrooms, 2 double beds
10–15 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds
12–17 Aug
5.0 out of 5 average rating, 212 reviews
Superhost
Home in Winter Park
Cute bungalow minutes walk from Park Ave.
2 bedrooms, 2 queen beds
7–13 Nov
4.96 out of 5 average rating, 27 reviews
Room in Orlando
Nice room with private bathroom
1 bed
6–11 Aug
Apartment in Casselberry
Cozy Private Apartment in Casselberry
2 bedrooms, 2 queen beds
9–14 Aug
New place to stay
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Guest house in Orlando
Cozy Modern Retreat | Patio | Self Check-In
1 queen bed
5–10 Aug
4.9 out of 5 average rating, 10 reviews
Home in Casselberry
Hilltop Haven – Peaceful Casselberry Getaway
3 bedrooms, 4 beds
7–12 Aug
New place to stay
Top guest favourite
Guest house in Orlando
Modern 1950s Studio • Near Downtown & Theme Parks
1 bedroom, 1 queen bed
10–15 Aug
4.97 out of 5 average rating, 176 reviews