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Search results; Over 1,000 homes in Winter Park

Guest favourite
Apartment in Winter Park
Charming 2/1 Condo on a Lake in Winter Park
2 bedrooms, 2 beds, 1 private bathroom
29 Oct – 3 Nov
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4.95 out of 5 average rating, 39 reviews
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
Guest favourite
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, 28 reviews
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
Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 3 reviews
Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 3 reviews
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
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
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 41 reviews
Room in Oviedo
Modern Oviedo Stay | Cozy & Peaceful Nature Suite
1 queen bed, 1 bathroom
12–17 Sept
New place to stay
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
23–28 Sept
5.0 out of 5 average rating, 106 reviews
Superhost
Home in Kissimmee
Magical Stay Near Disney
4 bedrooms, 5 beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Orlando
Modern 2BR Escape | King Bed • Pets • Epic U10 min
2 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Home in Orlando
4BR: Lakefront Retreat with Harry Potter Game Loft
4 bedrooms, 3 bathrooms
12–17 Oct
5.0 out of 5 average rating, 37 reviews
Home in Orlando
Fern Haven at Baldwin | Cozy Urban Retreat
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Orlando
Updated 2 Bdr • Close to Downtown + Advent Health
2 bedrooms, 2 king beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Altamonte Springs
Lake Marion Apt w/ Canoe in Altamonte Springs!
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.89 out of 5 average rating, 93 reviews
Guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
24–29 Sept
5.0 out of 5 average rating, 8 reviews
Home in Orlando
Cozy Orlando Getaway
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 3 reviews