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Search results; Over 1,000 homes in Winter Park

Guest favourite
Bungalow in Winter Park
Cozy 2/2 Home - Downtown Winterpark/Orlando
2 bedrooms, 2 beds, 2 private bathrooms
21–26 Sept
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4.97 out of 5 average rating, 352 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 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
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 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
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
Apartment in Orlando
4114-306 Spacious 3bd condo at Vista Cay Resort
3 bedrooms, 7 beds, 2 bathrooms
6–11 Oct
New place to stay
Top guest favourite
Home in Orlando
The Saphire, Milk District Gem! Unit 1
1 bedroom, 1 bed, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 30 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
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
Guest favourite
Flat in Altamonte Springs
Lake Marion Apt w/ Canoe in Altamonte Springs!
1 bedroom, 1 queen bed, 1 bathroom
5–10 Oct
4.89 out of 5 average rating, 93 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
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
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
College Park Villa Oasis w/ Botanical Courtyard
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 171 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
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
Top guest favourite
Home in Orlando
12BR Disney Luxury Retreat - Pool, Theater & Fun!
12 bedrooms, 21 beds, 11.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 57 reviews