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Search results; Over 1,000 homes in Winter Park

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Guest favourite
Home in Winter Park
Stylish newly updated home in Winter Park
3 bedrooms, 4 beds, 2 private bathrooms
4–9 Sept
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4.98 out of 5 average rating, 204 reviews
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Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Winter Park
Apt D -Modern Elegance in the Heart of Winter Park
2 bedrooms, 2 queen beds, 2 bathrooms
18–23 Sept
4.96 out of 5 average rating, 235 reviews
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Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Winter Park
Luxurious 2BR Near Park Ave & Rollins College
2 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 31 reviews
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Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds, 1 bathroom
30 Nov – 5 Dec
4.98 out of 5 average rating, 50 reviews
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Top guest favourite
Guest suite in Orlando
A SUITE RETREAT with a Garden View in the City
1 bedroom, 1 queen bed, 1 bathroom
10–15 Sept
4.97 out of 5 average rating, 479 reviews
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Flat in Orlando
Private Bamboo Oasis Apartment in College Park
1 bedroom, 1 bed, 1 bathroom
1–6 Sept
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Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 140 reviews
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Top guest favourite
Guest suite in Altamonte Springs
Guest Suite! Key West in Altamonte Springs!
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
4.96 out of 5 average rating, 447 reviews
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Top guest favourite
Treehouse in Orlando
Brand New Stylish & Unique Tree House!
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 81 reviews
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Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
9–16 Sept
5.0 out of 5 average rating, 24 reviews
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Guest favourite
Flat in Orlando
Massive Corner 3 Bedroom 2 Bath
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 5 reviews
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Superhost
Home in Winter Park
Cute bungalow minutes walk from Park Ave.
2 bedrooms, 2 queen beds, 2 bathrooms
7–13 Nov
4.96 out of 5 average rating, 27 reviews
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Top guest favourite
Home in Orlando
4BR: Lakefront Retreat with Harry Potter Game Loft
4 bedrooms, 3 bathrooms
22–27 Sept
5.0 out of 5 average rating, 37 reviews
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Superhost
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 64 reviews
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Home in Orlando
Fern Haven at Baldwin | Cozy Urban Retreat
1 bedroom, 2 beds, 1 bathroom
2–7 Sept
New place to stay
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Superhost
Flat in Orlando
Stylish King Bed Suite | Pool • Gym • Near Epic U
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 55 reviews
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Top guest favourite
Guest suite in Orlando
~Chic Oasis • 6-Guest Suite • Pool Heat • Near All
2 bedrooms, 3 beds, 1 bathroom
27 Nov – 2 Dec
4.97 out of 5 average rating, 448 reviews