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Search results; Over 1,000 homes in Winter Park

Bungalow in Winter Park
Charming Farmhouse Bungalow
3 bedrooms, 3 beds, 2 private bathrooms
6–11 Aug
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4.83 out of 5 average rating, 111 reviews
Top guest favourite
Flat in Winter Park
Apt D -Modern Elegance in the Heart of Winter Park
4.96 out of 5 average rating, 232 reviews, 2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
New place to stay, 4 bedrooms, 4 beds, 3.5 bathrooms
17–22 Jul
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
4.99 out of 5 average rating, 78 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Superhost
Flat in Winter Park
The Grove
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Aug
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
5.0 out of 5 average rating, 63 reviews, 2 bedrooms, 2 beds, 2 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in Winter Park
Modern 2BR Near Park Ave Perfect for Groups
5.0 out of 5 average rating, 24 reviews, 2 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds, 2.5 bathrooms
15–20 Aug
Home in Orlando
Hidden Oasis House - Pool, Gameroom in DT Orlando!
3 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Orlando
4BR: Lakefront Retreat with Harry Potter Game Loft
5.0 out of 5 average rating, 32 reviews, 4 bedrooms, 3 bathrooms
8–13 Aug
Home in Kissimmee
Modern Oasis with Private Pool
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
Guest favourite
Home in Orlando
2 King Beds • Minutes to AdventHealth + Downtown
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 4 bathrooms
19–24 Jul
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
5.0 out of 5 average rating, 212 reviews, 2 bedrooms, 2 beds, 1 bathroom
22–27 Jul
Top guest favourite
Bungalow in Orlando
Den on Daniels
4.97 out of 5 average rating, 138 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Jul
Superhost
Hotel in Winter Park
Large marble bathroom & Julius Meinl coffeemaker
1 bedroom, 1 bed, 1 bathroom
18–23 Jul
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
5.0 out of 5 average rating, 37 reviews, 4 bedrooms, 5 beds, 2 bathrooms
18–23 Jul
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
5.0 out of 5 average rating, 100 reviews, 3 bedrooms, 5 beds, 2 bathrooms
14–19 Aug
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
5.0 out of 5 average rating, 132 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Jul