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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Flat in Winter Park
Apt C -Modern Elegance in the Heart of Winter Park
2 bedrooms, 2 beds, 2 private bathrooms
24–29 Jul
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4.96 out of 5 average rating, 227 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
5.0 out of 5 average rating, 61 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Guest house in Orlando
Location, Location, Location!
4.99 out of 5 average rating, 129 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Home in Winter Park
Modern 2BR Near Park Ave Perfect for Groups
5.0 out of 5 average rating, 22 reviews, 2 bedrooms, 4 beds, 2 bathrooms
17–22 Jul
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
4.99 out of 5 average rating, 77 reviews, 3 bedrooms, 3 beds, 1 bathroom
26–31 Jul
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 3 beds, 1 bathroom
31 Jul – 5 Aug
Townhouse in Orlando
Sweet Orlando getaway Near Disney World/Universal.
New place to stay, 3 bedrooms, 3 beds, 2.5 bathrooms
11–16 Jul
Guest favourite
Home in Orlando
Lake Eola Retreat + Private Hot Tub & Yard + Grill
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
19–24 Jul
Top guest favourite
Home in Orlando
Sunny Oasis: Downtown Orlando with Suburban feel
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 2 beds, 2 bathrooms
13–18 Jul
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
5.0 out of 5 average rating, 211 reviews, 2 bedrooms, 2 beds, 1 bathroom
3–8 Jul
Top guest favourite
Home in Orlando
Home New Cozy & Stylish sleep5/2bath primelocation
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 4 beds, 4 bathrooms
26–31 Jul
Home in Kissimmee
Santosh Cove Retreat
New place to stay, 4 bedrooms, 5 beds, 3.5 bathrooms
31 Aug – 5 Sept
Top guest favourite
Tiny home in Orlando
Completely Private Tiny Home! East ORL./ UCF area.
5.0 out of 5 average rating, 9 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Home in Kissimmee
Orlando Dream Escape | Private Pool | Disney
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Orlando
4BR: Lakefront Retreat with Harry Potter Game Loft
5.0 out of 5 average rating, 29 reviews, 4 bedrooms, 5 beds, 3 bathrooms
8–13 Aug
Place to stay in Altamonte Springs
Comfy Room | Game Room | Near Disney & Universal
New place to stay, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Guest house in Orlando
The Sacred Space Downtown Orlando Milk District
5.0 out of 5 average rating, 264 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Jul
Guest favourite
Flat in Orlando
Spacious2BR PetFriendly Oasis Sleeps 6, Pool &Gym
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Jul