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Search results; Over 1,000 homes in Winter Park

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Superhost
Guest house in Winter Park
Cozy guest house close to Downtown Orlando
1 bedroom, 2 beds, 1 private bathroom
7–12 Sept
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4.86 out of 5 average rating, 195 reviews
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Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed
6–11 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds
16–21 Sept
5.0 out of 5 average rating, 6 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
18–23 Sept
4.96 out of 5 average rating, 235 reviews
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Top guest favourite
Home in Winter Park
Luxurious 2BR Near Park Ave & Rollins College
2 bedrooms, 4 beds
6–11 Sept
5.0 out of 5 average rating, 31 reviews
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Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds
20–25 Sept
5.0 out of 5 average rating, 65 reviews
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Superhost
Home in Winter Park
Cute bungalow minutes walk from Park Ave.
2 bedrooms, 2 queen beds
7–13 Nov
4.96 out of 5 average rating, 27 reviews
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Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds
9–14 Sept
5.0 out of 5 average rating, 41 reviews
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Home in Kissimmee
Pool Home 10min from Disney
4 bedrooms, 8 beds
7–13 Sept
5.0 out of 5 average rating, 3 reviews
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Home in Casselberry
Casselberry: Pool, sleep 12, GameRoom, Playground
5 bedrooms, 12 beds
6–11 Sept
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
5–10 Sept
5.0 out of 5 average rating, 8 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 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Orlando
AirPort & Downtown Orlando 15 min| Disney 30 min
3 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Home in Orlando
The Saphire, Milk District Gem! Unit 1
1 bedroom, 1 bed
1–6 Sept
5.0 out of 5 average rating, 30 reviews
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Guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds
4–9 Sept
5.0 out of 5 average rating, 6 reviews
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Room in Winter Park
Quiet, comfortable room in Orlando (Winter Park)
1 bed
1–6 Sept
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Flat in Orlando
Private Bamboo Oasis Apartment in College Park
1 bedroom, 1 bed
1–6 Sept
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Home in Orlando
Fern Haven at Baldwin | Cozy Urban Retreat
1 bedroom, 2 beds
2–7 Sept
New place to stay
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Superhost
Home in Kissimmee
3 Epic Theme Rooms • Sleeps 27 • Pool/Spa • Disney
9 bedrooms, 14 beds
7–12 Sept
New place to stay