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Search results; Over 1,000 homes in Winter Park

Guest favourite
Home in Winter Park
Gem. Downtown Winter park, walk to Park av/Rollins
3 bedrooms, 6 beds, 2 private bathrooms
26–31 Jul
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4.89 out of 5 average rating, 142 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
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
2–7 Aug
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
8–13 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
Home in Orlando
Hidden Oasis House - Pool, Gameroom in DT Orlando!
3 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds, 2.5 bathrooms
15–20 Aug
Top guest favourite
Home in Longwood
The Lakefront Brantley House
5.0 out of 5 average rating, 23 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
22–29 Jul
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
5.0 out of 5 average rating, 101 reviews, 3 bedrooms, 5 beds, 2 bathrooms
20–25 Aug
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
2–7 Aug
Top guest favourite
Bungalow in Orlando
Den on Daniels
4.98 out of 5 average rating, 139 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Jul
Top guest favourite
Guest house in Orlando
The Sacred Space Downtown Orlando Milk District
5.0 out of 5 average rating, 266 reviews, 1 bedroom, 1 bed, 1 bathroom
6–11 Aug
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Flat in Orlando
Spacious2BR PetFriendly Oasis Sleeps 6, Pool &Gym
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 4 bathrooms
26–31 Jul
Superhost
Home in Kissimmee
5 BD/ 4 BA/ Terra Verde (4669 GB)
5 bedrooms, 7 beds, 4 bathrooms
30 Jul – 4 Aug
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
4.98 out of 5 average rating, 44 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Oct