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Search results; Over 1,000 homes in Winter Park

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Guest favourite
Home in Winter Park
Gem Vacation Winter Park
3 bedrooms, 4 beds, 2 private bathrooms
21–26 Sept
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4.87 out of 5 average rating, 39 reviews
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Guest house in Winter Park
Private Winter Park Studio with Parking
1 bed
20–25 Sept
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, 7 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 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 Orlando
AirPort & Downtown Orlando 15 min| Disney 30 min
3 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
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Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed
20–25 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
20–25 Sept
5.0 out of 5 average rating, 3 reviews
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Room in Winter Park
LBeTwo Queen desk closet
1 bed
19–24 Sept
New place to stay
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Apartment in Orlando
4114-306 Spacious 3bd condo at Vista Cay Resort
3 bedrooms, 7 beds
9–14 Nov
New place to stay
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Home in Orlando
Cozy Orlando Getaway
2 bedrooms, 2 beds
20–25 Sept
5.0 out of 5 average rating, 4 reviews
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Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed
24–29 Sept
5.0 out of 5 average rating, 3 reviews
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Room in Oviedo
Modern Oviedo Stay | Cozy & Peaceful Nature Suite
1 queen bed
21–26 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in Orlando
4BR: Lakefront Retreat with Harry Potter Game Loft
4 bedrooms
12–17 Oct
5.0 out of 5 average rating, 37 reviews
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Home in Kissimmee
Disney Area 4 BR| Private Pool & Free Water Park
4 bedrooms, 6 beds
20–25 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
19–24 Oct
5.0 out of 5 average rating, 42 reviews
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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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Top guest favourite
Guest house in Orlando
1924 Spanish Carriage House Lower
1 bedroom, 2 beds
8–13 Oct
4.98 out of 5 average rating, 154 reviews
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Home in Orlando
Fern Haven at Baldwin | Cozy Urban Retreat
1 bedroom, 2 beds
19–24 Sept
5.0 out of 5 average rating, 3 reviews