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Search results; Over 1,000 homes in Winter Park

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Guest favourite
Home in Winter Park
2 Min to Park Ave | Charming Winter Park Bungalow
2 bedrooms, 2 beds, 1 private bathroom
10–15 Oct
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4.89 out of 5 average rating, 90 reviews
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Superhost
Home in Winter Park
Charming Winter Park Retreat
3 bedrooms, 3 beds, 2 bathrooms
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, 3.5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 7 reviews
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Featured hotel
Hotel in Winter Park
The Alfond Inn, Parlor king
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
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
Home in Orlando
AirPort & Downtown Orlando 15 min| Disney 30 min
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 23 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
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 42 reviews
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Home in Orlando
Fern Haven at Baldwin | Cozy Urban Retreat
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Room in Winter Park
LBeTwo Queen desk closet
1 bed, 1 bathroom
1–6 Oct
New place to stay
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Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds, 2.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 8 reviews
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Home in Kissimmee
Disney Area 4 BR| Private Pool & Free Water Park
4 bedrooms, 6 beds, 3 bathrooms
9–14 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Flat in Orlando
Modern 2BR Escape | King Bed • Pets • Epic U10 min
2 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 49 reviews
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Guest favourite
Room in Orlando
Orlando Comfort
2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 5 reviews
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Home in Orlando
The Escape Village | 8 PPL | Pool | Fire Pit | BBQ
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Orlando
College Park • 2 Kings • WorkSpace • AdventHealth
2 bedrooms, 2 king beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 6 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, 155 reviews
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Apartment in Orlando
4114-306 Spacious 3bd condo at Vista Cay Resort
3 bedrooms, 7 beds, 2 bathrooms
9–14 Nov
New place to stay