Search results; Over 1,000 homes in Winter Park

Superhost
Home in Winter Park
Cute bungalow minutes walk from Park Ave.
2 bedrooms, 2 beds, 2 private bathrooms
7–13 Nov
,
4.96 out of 5 average rating, 26 reviews
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
3 bedrooms, 3 beds
21–26 Jun
4.99 out of 5 average rating, 75 reviews
Top guest favourite
Home in Winter Park
Modern 2BR Near Park Ave Perfect for Groups
2 bedrooms, 4 beds
30 Jun – 5 Jul
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds
2–7 Jul
5.0 out of 5 average rating, 59 reviews
Top guest favourite
Guest house in Orlando
The Sacred Space Downtown Orlando Milk District
1 bedroom, 1 queen bed
19–24 Jun
5.0 out of 5 average rating, 261 reviews
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds
5–10 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds
5–10 Jul
5.0 out of 5 average rating, 94 reviews
Top guest favourite
Guest house in Orlando
Modern 1950s Studio • Near Downtown & Theme Parks
1 bedroom, 1 queen bed
31 Jul – 5 Aug
4.97 out of 5 average rating, 168 reviews
Superhost
Home in Orlando
Tropical Oasis|Lounge|Putting Green|Heated Pool
3 bedrooms, 6 beds
22–27 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds
18–25 Jul
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Orlando
Eola Retreat + Private Hot Tub + Grill
2 bedrooms, 2 beds
19–24 Jul
5.0 out of 5 average rating, 13 reviews
Home in Kissimmee
Orlando Dream Escape
3 bedrooms, 4 beds
2–7 Aug
New place to stay
Top guest favourite
Bungalow in Orlando
Den on Daniels
1 bedroom, 1 bed
28 Jun – 3 Jul
4.98 out of 5 average rating, 134 reviews
Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds
11–16 Jul
5.0 out of 5 average rating, 5 reviews
Superhost
Apartment in Kissimmee
3121 Modern Condo Near Disney | Storey Lake Resort
2 bedrooms, 4 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds
17–22 Oct
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Guest house in Orlando
The Cottage A Pet Friendly Guesthouse
1 bedroom, 1 king bed
18–23 Jul
4.98 out of 5 average rating, 130 reviews
Guest favourite
Flat in Orlando
Spacious2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds
15–20 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds
21–26 Jun
4.91 out of 5 average rating, 90 reviews