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Search results; Over 1,000 homes in Winter Park

Guest favourite
Home in Winter Park
Stylish newly updated home in Winter Park
3 bedrooms, 4 beds, 2 private bathrooms
1–6 Oct
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4.98 out of 5 average rating, 207 reviews
Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 3 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
14–19 Sept
5.0 out of 5 average rating, 3 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
Flat in Orlando
Spacious2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 18 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
13–18 Sept
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
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
Home in Kissimmee
Bloom & Roam — Where Comfort Meets Vacation
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
New place to stay
Top guest favourite
Home in Orlando
Knight Light House | Chic UCF Stay
4 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Orlando
Updated 2 Bdr • Close to Downtown + Advent Health
2 bedrooms, 2 king beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Kissimmee
Magical Stay Near Disney
4 bedrooms, 5 beds, 3 bathrooms
26 Sept – 1 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
Featured hotel
Hotel in Kissimmee
Family double queen room
1 bedroom, 2 queen beds, 1 bathroom
12–17 Sept
Home in Orlando
Cozy Orlando Getaway
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 4 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