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Search results; Over 1,000 homes in Winter Park

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Home in Winter Park
Gem. Downtown Winter park, walk to Park av/Rollins
3 bedrooms, 6 beds, 2 private bathrooms
15–20 Nov
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4.9 out of 5 average rating, 143 reviews
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Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 7 reviews
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Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 65 reviews
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Top guest favourite
Guest house in Winter Park
Vibrant cottage in charming, unique Florida town
1 bedroom, 1 queen bed, 1 bathroom
22–27 Sept
5.0 out of 5 average rating, 10 reviews
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Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed, 1 bathroom
24–29 Sept
5.0 out of 5 average rating, 3 reviews
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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
19–24 Sept
5.0 out of 5 average rating, 142 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
18–23 Nov
4.98 out of 5 average rating, 482 reviews
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Top guest favourite
Home in Orlando
The Saphire, Milk District Gem! Unit 1
1 bedroom, 1 bed, 1 bathroom
24–29 Sept
5.0 out of 5 average rating, 30 reviews
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Home in Orlando
The Escape Village | 8 PPL | Pool | Fire Pit | BBQ
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
New place to stay
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Top guest favourite
Guest house in Orlando
College Park Villa Oasis w/ Botanical Courtyard
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 171 reviews
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Top guest favourite
Tiny home in Orlando
Cozy efficiency with kitchenette. Pet friendly
1 bedroom, 1 queen bed, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 20 reviews
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Guest house in Orlando
The Serene Suite Orlando
1 bedroom, 1 queen bed, 1 bathroom
30 Sept – 5 Oct
New place to stay
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Flat in Orlando
Carriage House w/ Office - Thornton Park/Lake Eola
1 bedroom, 2 beds, 1 bathroom
23–28 Oct
New place to stay
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Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 215 reviews
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Top guest favourite
Room in Orlando
Bright & Cozy • Hourglass District • Walkable
1 bed, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
20–25 Sept
5.0 out of 5 average rating, 24 reviews
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Guest favourite
Room in Orlando
Stylish Private bd/bth. 5% wkly/10% mthly discount
1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Guest house in Orlando
1924 Spanish Carriage House Lower
1 bedroom, 2 beds, 1 bathroom
8–13 Oct
4.98 out of 5 average rating, 154 reviews