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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Home in Winter Park
10 min to Winter Park, Games, Gym, King bd, Coffee
3 bedrooms, 4 beds, 2 private bathrooms
15–20 Sept
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4.95 out of 5 average rating, 75 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
Room in Winter Park
Winter Park. room1
1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 5 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
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
18–23 Oct
5.0 out of 5 average rating, 42 reviews
Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 3 reviews
Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed, 1 bathroom
24–29 Sept
5.0 out of 5 average rating, 3 reviews
Home in Orlando
Cozy Orlando Getaway
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews
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
Flat in Kissimmee
Close to everything, spacious, and comfortable
3 bedrooms, 5 beds, 2 bathrooms
31 Oct – 5 Nov
New place to stay
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
Apartment in Orlando
IS3-205 - 3BR condo near Disney with lake view
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.9 out of 5 average rating, 126 reviews
Home in Orlando
Fern Haven at Baldwin | Cozy Urban Retreat
1 bedroom, 2 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Orlando
College Park • 2 Kings • WorkSpace • AdventHealth
2 bedrooms, 2 king beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 6 reviews
Flat in Orlando
Carriage House w/ Office - Thornton Park/Lake Eola
1 bedroom, 2 beds, 1 bathroom
23–28 Oct
New place to stay
Top guest favourite
Guest house in Orlando
1924 Spanish Carriage House Lower
1 bedroom, 2 beds, 1 bathroom
8–13 Oct
4.98 out of 5 average rating, 154 reviews
Superhost
Home in Kissimmee
Magical Stay Near Disney
4 bedrooms, 5 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Home in Orlando
Luxury 2BR Home | Private Patio & Stylish Stay
2 bedrooms, 2 king beds, 1 bathroom
25–30 Sept
New place to stay