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Search results; Over 1,000 places in Winter Park

Superhost
Home in Winter Park
Charming home @wp. Patio +Gazebo. close to highwys
6 beds
Apr 2 – 7
4.67 out of 5 average rating, 18 reviews
Superhost
Apartment in Maitland
At Mine | Double Suite in Orlando
2 double beds
Apr 1 – 6
4.82 out of 5 average rating, 169 reviews
Guest favorite
Home in Orlando
Cheerful 4-bedroom with large and lush back yard.
5 beds
Apr 6 – 11
4.87 out of 5 average rating, 47 reviews
Guest favorite
Home in Winter Park
Tiny Home - 3 MI to Downtown & Winter Park
2 queen beds
Apr 14 – 19
4.95 out of 5 average rating, 61 reviews
Guest favorite
Guesthouse in Orlando
Amazing place in exclusive area Downtown Orlando
1 queen bed
Apr 2 – 7
4.93 out of 5 average rating, 44 reviews
Superhost
Home in Winter Park
Mills House @WP. Sleeps 11 Renovated. Queen beds
6 beds
Apr 14 – 19
4.84 out of 5 average rating, 85 reviews
Guest favorite
Guesthouse in Orlando
New Mid Century-Modern Studio
1 bed
May 24 – 29
4.96 out of 5 average rating, 24 reviews
Guest favorite
Bungalow in Winter Park
Cozy 2/2 Bungalow - Downtown Winterpark/Orlando
2 queen beds
Apr 14 – 19
4.98 out of 5 average rating, 224 reviews
Guest favorite
Apartment in Orlando
Quiet Shed in Downtown
1 queen bed
Apr 5 – 10
4.95 out of 5 average rating, 613 reviews
Guest favorite
Home in Orlando
Yale House in College Park 2 mi from Downtown
2 beds
Apr 1 – 6
4.92 out of 5 average rating, 53 reviews
Guest favorite
Home in Winter Park
Stylish newly updated home in Winter Park
4 beds
Apr 8 – 13
5.0 out of 5 average rating, 48 reviews
Guest favorite
Home in Winter Park
Cozy Winter Park Home
4 beds
Apr 1 – 6
5.0 out of 5 average rating, 26 reviews
Guest favorite
Home in Orlando
Colonialtown Bungalow
2 beds
Apr 7 – 12
4.91 out of 5 average rating, 11 reviews
Superhost
Villa in Winter Park
As close as you can stay to Rollins College!
2 beds
Apr 1 – 6
4.91 out of 5 average rating, 34 reviews
Guest favorite
Home in Orlando
Charming 2BR Cottage, Downtown Orlando
Apr 14 – 19
4.95 out of 5 average rating, 19 reviews
Guest favorite
Townhouse in Orlando
★Modern DT Home★King Bed☀️Patios✔Long Stays⚡️WiFi★
3 beds
Apr 21 – 26
4.95 out of 5 average rating, 138 reviews
Guest favorite
Home in Winter Park
Charming Retreat In Winter Park
4 beds
Apr 21 – 26
4.94 out of 5 average rating, 18 reviews
Guest favorite
Home in Orlando
The Villa Orlando@College Park. Sleeps16.
7 beds
May 19 – 24
4.98 out of 5 average rating, 62 reviews