Search results; Over 1,000 homes in Winter Park

Top guest favourite
Flat in Winter Park
Apt C -Modern Elegance in the Heart of Winter Park
2 bedrooms, 2 beds, 2 private bathrooms
24–29 Jul
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4.96 out of 5 average rating, 227 reviews
Top guest favourite
Home in Winter Park
Modern 2BR Near Park Ave Perfect for Groups
2 bedrooms, 4 beds, 2 bathrooms
17–22 Jul
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 61 reviews
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
3 bedrooms, 3 beds, 1 bathroom
6–11 Jul
4.99 out of 5 average rating, 77 reviews
Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed, 1 bathroom
3–10 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
18–23 Jul
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Home in Orlando
Home New Cozy & Stylish sleep5/2bath primelocation
2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 5 reviews
Superhost
Hotel in Winter Park
Large marble bathroom & Julius Meinl coffeemaker
1 bedroom, 1 king bed, 1 bathroom
1–6 Jul
Top guest favourite
Flat in Orlando
3BR Stylish King Family• Pets • Pool • Gym Near Ep
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 45 reviews
Superhost
Home in Orlando
Pet friendly pool home in milk district!
3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 4 reviews
Home in Orlando
New & Private Studio in DT Orlando (Thornton Park)
1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds, 1 bathroom
1–6 Jul
5.0 out of 5 average rating, 211 reviews
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom, 1 queen bed, 1 bathroom
9–14 Jul
5.0 out of 5 average rating, 133 reviews
Hotel in Altamonte Springs
Minutes to Kia Center + Breakfast. Kitchen. Pool.
2 bedrooms, 2 king beds, 2 bathrooms
4–9 Jul
New place to stay
Top guest favourite
Home in Orlando
Sunny Oasis: Downtown Orlando with Suburban feel
2 bedrooms, 2 double beds, 2 bathrooms
13–18 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Bungalow in Orlando
Den on Daniels
1 bedroom, 1 bed, 1 bathroom
5–10 Jul
4.98 out of 5 average rating, 135 reviews
Top guest favourite
Guest house in Orlando
College Park Villa Oasis w/ Botanical Courtyard
1 bedroom, 1 queen bed, 1 bathroom
4–9 Jul
4.99 out of 5 average rating, 168 reviews
Flat in Orlando
Cozy 2BR Apt | Near Universal & International Dr
2 bedrooms, 4 beds, 2 bathrooms
11–16 Aug
New place to stay
Top guest favourite
Home in Orlando
12BR Disney Luxury Retreat - Pool, Theater & Fun!
12 bedrooms, 21 beds, 11.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 51 reviews