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Search results; Over 1,000 homes in Winter Park

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Guest favourite
Home in Winter Park
Gem Vacation Winter Park
3 bedrooms, 4 beds, 2 private bathrooms
4–9 Oct
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4.87 out of 5 average rating, 39 reviews
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Featured hotel
Hotel in Winter Park
The Alfond Inn, Parlor king
1 bedroom, 1 king bed
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Superhost
Home in Winter Park
Charming Winter Park Retreat
3 bedrooms, 3 beds
1–6 Oct
New place to stay
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Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds
3–8 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds
12–17 Oct
5.0 out of 5 average rating, 65 reviews
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Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed
1–6 Oct
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
5–10 Oct
5.0 out of 5 average rating, 144 reviews
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Guest favourite
Home in Orlando
College Park • 2 Kings • WorkSpace • AdventHealth
2 bedrooms, 2 king beds
1–6 Oct
5.0 out of 5 average rating, 6 reviews
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Flat in Orlando
Carriage House w/ Office - Thornton Park/Lake Eola
1 bedroom, 2 beds
19–24 Oct
New place to stay
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Top guest favourite
Guest house in Winter Park
Vibrant cottage in charming, unique Florida town
1 bedroom, 1 queen bed
1–6 Oct
5.0 out of 5 average rating, 10 reviews
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Guest house in Orlando
The Serene Suite Orlando
1 bedroom, 1 queen bed
1–6 Oct
New place to stay
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Guest favourite
Room in Orlando
Orlando Comfort
2 beds
4–9 Oct
5.0 out of 5 average rating, 5 reviews
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Home in Orlando
Fern Haven at Baldwin | Cozy Urban Retreat
1 bedroom, 2 beds
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Tiny home in Orlando
Cozy efficiency with kitchenette. Pet friendly
1 bedroom, 1 queen bed
1–6 Oct
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Home in Orlando
AirPort & Downtown Orlando 15 min| Disney 30 min
3 bedrooms, 5 beds
1–6 Oct
5.0 out of 5 average rating, 23 reviews
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Guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds
1–6 Oct
5.0 out of 5 average rating, 8 reviews
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Home in Orlando
Cozy Orlando Getaway
2 bedrooms, 2 beds
4–9 Oct
5.0 out of 5 average rating, 4 reviews
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Flat in Orlando
Elevated Living Apt
1 bedroom, 1 bed
8–13 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Flat in Orlando
Luxe Stay | King Bed • Pool • Gym • 10 min to Epic
1 bedroom, 2 beds
1–6 Oct
5.0 out of 5 average rating, 20 reviews