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Search results; Over 1,000 homes in Winter Park

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Guest suite in Winter Park
Modern Guest Suite near Full Sail in Winter Park
1 bedroom, 1 bed, 1 private bathroom
6–11 Sept
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4.86 out of 5 average rating, 246 reviews
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Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
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, 2 bathrooms
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, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 31 reviews
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Superhost
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 64 reviews
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Superhost
Home in Winter Park
Cute bungalow minutes walk from Park Ave.
2 bedrooms, 2 queen beds, 2 bathrooms
7–13 Nov
4.96 out of 5 average rating, 27 reviews
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Home in Casselberry
Casselberry: Pool, sleep 12, GameRoom, Playground
5 bedrooms, 12 beds, 4 bathrooms
6–11 Sept
New place to stay
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Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 41 reviews
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Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds, 2.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 8 reviews
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Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 3 reviews
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Room in Winter Park
Quiet, comfortable room in Orlando (Winter Park)
1 bed, 1 bathroom
1–6 Sept
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Top guest favourite
Home in Orlando
AirPort & Downtown Orlando 15 min| Disney 30 min
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 20 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 Sept
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 Sept
5.0 out of 5 average rating, 6 reviews
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Home in Orlando
Fern Haven at Baldwin | Cozy Urban Retreat
1 bedroom, 2 beds, 1 bathroom
2–7 Sept
New place to stay
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Flat in Orlando
Private Bamboo Oasis Apartment in College Park
1 bedroom, 1 bed, 1 bathroom
1–6 Sept
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Top guest favourite
Home in Orlando
The Saphire, Milk District Gem! Unit 1
1 bedroom, 1 bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 30 reviews
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Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
4.93 out of 5 average rating, 15 reviews
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Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 11 reviews