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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Cottage in Winter Park
Winter Park Pearl 6 min drive to historic Park Ave
3 bedrooms, 3 beds, 1.5 private bathrooms
1–6 Aug
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4.95 out of 5 average rating, 463 reviews
Guest favourite
Flat in Winter Park
The Grove
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Top guest favourite
Guest suite in Orlando
A SUITE RETREAT with a Garden View in the City
4.97 out of 5 average rating, 474 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
Top guest favourite
Home in Winter Park
Modern 2BR Near Park Ave Perfect for Groups
5.0 out of 5 average rating, 26 reviews, 2 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Top guest favourite
Guest house in Orlando
Modern 1950s Studio • Near Downtown & Theme Parks
4.97 out of 5 average rating, 175 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
4.99 out of 5 average rating, 80 reviews, 3 bedrooms, 3 beds, 1 bathroom
12–17 Aug
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
5.0 out of 5 average rating, 212 reviews, 2 bedrooms, 2 beds, 1 bathroom
3–8 Aug
Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
5.0 out of 5 average rating, 134 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Home in Orlando
2 King Beds • Minutes to AdventHealth + Downtown
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Guest house in Orlando
Amazing New Pool House!
4.98 out of 5 average rating, 109 reviews, 1 bedroom, 2 beds, 1 bathroom
17–22 Aug
Superhost
Flat in Orlando
Luxury 1BR & Resort Amenities + 6min to Epic-Unive
New place to stay, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Guest suite in Orlando
LAKEFRONT STUDIO APARTMENT (private entrance)
5.0 out of 5 average rating, 485 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Home in Orlando
New SunRise Cozy & Stylish Home sleep5/2bath
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
Guest favourite
Guest house in Orlando
Cozy Modern Retreat | Patio | Self Check-In
5.0 out of 5 average rating, 6 reviews, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Home in Orlando
Sunny Oasis: Downtown Orlando with Suburban feel
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 2 bathrooms
4–9 Aug
Top guest favourite
Place to stay in Orlando
Handicap Accessible Master room
5.0 out of 5 average rating, 20 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jan – 1 Feb
Guest favourite
Flat in Orlando
King Bed Haven, Amazing Pool, Gym, & Pet-Friendly
5.0 out of 5 average rating, 8 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug