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Search results; Over 1,000 homes in Winter Park

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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 Oct
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4.95 out of 5 average rating, 468 reviews
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Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed
4–9 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
10–15 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, 8 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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Superhost
Flat in Orlando
Modern 1King Bed w/ Resort Pool, Gym&Pets-Friendly
1 bedroom, 2 beds
1–6 Oct
New place to stay
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Top guest favourite
Flat in Orlando
Luxury 1BR & Resort Amenities - 6min to Epic-Uni
1 bedroom, 2 beds
1–6 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds
2–7 Oct
4.98 out of 5 average rating, 43 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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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, 25 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, 21 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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Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds
11–16 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds
1–6 Oct
5.0 out of 5 average rating, 9 reviews
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Superhost
Home in Kissimmee
8BR house with private pool in Bella Vida Resort
8 bedrooms, 8 beds
15–20 Oct
New place to stay
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Superhost
Flat in Orlando
Spacious 2BR PetFriendly Oasis Sleeps6, Pool &Gym
2 bedrooms, 3 beds
1–6 Oct
New place to stay
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Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds
18–23 Oct
5.0 out of 5 average rating, 107 reviews
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Guest favourite
Room in Orlando
Orlando Comfort
2 beds
4–9 Oct
5.0 out of 5 average rating, 6 reviews