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Search results; Over 1,000 homes in Winter Park

Superhost
Home in Winter Park
Cheerful 3 bedroom with a spacious shaded yard
3 bedrooms, 15 beds, 2 private bathrooms
8–13 Nov
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4.9 out of 5 average rating, 136 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
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
15–20 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
Home in Orlando
Luxury 2BR Home | Private Patio & Stylish Stay
2 bedrooms, 2 king beds, 1 bathroom
14–19 Sept
New place to stay
Guest favourite
Home in Orlando
Updated 2 Bdr • Close to Downtown + Advent Health
2 bedrooms, 2 king beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 6 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
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
Flat in Orlando
Spacious2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 18 reviews
Superhost
Home in Four Corners
7 Bd/ 5.5 Ba/ Windsor Cay (1028 Bp)
7 bedrooms, 10 beds, 5 bathrooms
20–25 Sept
Top guest favourite
Flat in Orlando
Spacious 2BR Oasis, Sleeps 8 Near Orlando Parks
2 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 7 reviews
Home in Orlando
Fern Haven at Baldwin | Cozy Urban Retreat
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Kissimmee
Luxe Family Escape | Pool Oasis Near Disney
4 bedrooms, 6 beds, 3 bathrooms
20–25 Sept
New place to stay
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 214 reviews
Top guest favourite
Guest house in Orlando
The Sacred Space Downtown Orlando Milk District
1 bedroom, 1 queen bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 270 reviews
Room in Oviedo
Modern Oviedo Stay | Cozy & Peaceful Nature Suite
1 queen bed, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 3 reviews