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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
1–6 Aug
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4.95 out of 5 average rating, 463 reviews
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
2–7 Aug
Top guest favourite
Home in Winter Park
Modern 2BR Near Park Ave Perfect for Groups
5.0 out of 5 average rating, 26 reviews, 2 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Guest favourite
Flat in Winter Park
The Grove
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Top guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
4.99 out of 5 average rating, 80 reviews, 3 bedrooms, 3 beds, 1 bathroom
11–16 Aug
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
5.0 out of 5 average rating, 39 reviews, 4 bedrooms, 5 beds, 2 bathrooms
2–7 Aug
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds, 2.5 bathrooms
15–20 Aug
Guest favourite
Home in Orlando
New SunRise Cozy & StylishHome sleep5/2bath
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Home in Longwood
Central Florida Pool Home
4.96 out of 5 average rating, 54 reviews, 3 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
Guest favourite
Home in Orlando
Magazine like huge home w/ pool city center/parks
5.0 out of 5 average rating, 6 reviews, 7 bedrooms, 7 beds, 6.5 bathrooms
31 Aug – 5 Sept
Home in Orlando
Hidden Oasis House - Pool, Gameroom in DT Orlando!
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 5 beds, 2 bathrooms
2–7 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
22–27 Aug
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
4.98 out of 5 average rating, 45 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Nov
Home in Orlando
Orlando Escape • Near Disney • 5 Bedrooms
New place to stay, 5 bedrooms, 5 beds, 4 bathrooms
1–6 Aug
Home in Ocoee
Serenity Retreat
New place to stay, 2 bedrooms, 2 beds, 2 bathrooms
10–15 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
5–10 Aug
Apartment in Casselberry
Cozy Private Apartment in Casselberry
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Superhost
Townhouse in Orlando
New Vista Cay Home | Universal & Convention
New place to stay, 3 bedrooms, 4 beds, 3.5 bathrooms
2–7 Aug