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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
20–25 Sept
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4.95 out of 5 average rating, 467 reviews
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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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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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Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed, 1 bathroom
22–27 Sept
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, 2.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 8 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
27 Sept – 2 Oct
5.0 out of 5 average rating, 23 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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Guest house in Orlando
The Serene Suite Orlando
1 bedroom, 1 queen bed, 1 bathroom
30 Sept – 5 Oct
New place to stay
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Featured hotel
Hotel in Winter Park
The Alfond Inn, Parlor king
1 bedroom, 1 king bed, 1 bathroom
24–29 Sept
5.0 out of 5 average rating, 3 reviews
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Home in Orlando
The Escape Village | 8 PPL | Pool | Fire Pit | BBQ
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Guest house in Orlando
College Park Villa Oasis w/ Botanical Courtyard
1 bedroom, 1 queen bed, 1 bathroom
22–27 Sept
4.99 out of 5 average rating, 171 reviews
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Guest favourite
Home in Orlando
College Park • 2 Kings • WorkSpace • AdventHealth
2 bedrooms, 2 king beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 144 reviews
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Top guest favourite
Flat in Orlando
Spacious 2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 16 reviews
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Home in Orlando
Fern Haven at Baldwin | Cozy Urban Retreat
1 bedroom, 2 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 3 reviews
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Home in Orlando
Cozy Orlando Getaway
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews
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Flat in Orlando
Private 2-Queen Apt Near MCO with Patio
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 4 reviews
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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 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 10 reviews
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Room in Winter Park
LBeTwo Queen desk closet
1 bed, 1 bathroom
26 Sept – 1 Oct
New place to stay