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Search results; Over 1,000 places in Winter Park

Superhost
Apartment in Maitland
At Mine | Elegant Double Suite in North Orlando
2 double beds
Apr 1 – 6
4.83 out of 5 average rating, 223 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
Guesthouse in Winter Park
Cozy guest house close to Downtown Orlando
2 beds
May 29 – Jun 3
4.85 out of 5 average rating, 106 reviews
Guest favorite
Cottage in Winter Park
Winter Park Pearl 6 min drive to historic Park Ave
2 beds
Apr 2 – 7
4.96 out of 5 average rating, 337 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
Townhouse in Winter Park
Beautiful Downtown Winter Park
1 queen bed
May 30 – Jun 4
4.98 out of 5 average rating, 195 reviews
Guest favorite
Home in Winter Park
Winter Park guest suite near UCF/FullSail/Rollins
1 bed
Apr 12 – 18
4.95 out of 5 average rating, 21 reviews
Guest favorite
Guesthouse in Winter Park
WELCOME HOME IN WINTER PARK
1 queen bed
Apr 19 – 24
4.81 out of 5 average rating, 231 reviews
Guest suite in Winter Park
Comfortable Studio
1 queen bed
Apr 5 – 10
4.82 out of 5 average rating, 11 reviews
Superhost
Apartment in Maitland
At Mine | King Suite In North Orlando
1 king bed
Apr 1 – 6
4.79 out of 5 average rating, 95 reviews
Condo in Winter Park
Lovely 1 BR Condo/Steps Away From Shopping Mart!
1 bed
Apr 7 – 12
4.76 out of 5 average rating, 38 reviews
Superhost
Home in Winter Park
𝕊𝕝𝕖𝕖𝕡𝕤 𝟠| 𝕎𝕚𝕟𝕥𝕖𝕣 ℙ𝕒𝕣𝕜|ᴏʀʟᴀɴᴅᴏ
4 beds
Apr 1 – 6
4.89 out of 5 average rating, 63 reviews
Guest favorite
Home in Maitland
The Butterfly Bungalow near Park Ave
2 beds
Apr 7 – 12
4.96 out of 5 average rating, 112 reviews
Villa in Winter Park
Balfour Villa
Apr 22 – 27
4.75 out of 5 average rating, 73 reviews
Guest favorite
Apartment in Winter Park
The Lake House
2 beds
Apr 28 – May 3
4.89 out of 5 average rating, 28 reviews
Guest favorite
Condo in Winter Park
Charming 2/1 Condo on a Lake in Winter Park
2 beds
Aug 2 – 7
4.93 out of 5 average rating, 27 reviews
Superhost
Guest suite in Orlando
Backyard Paradise! Studio Guesthouse with Patio
1 queen bed
Apr 6 – 11
4.85 out of 5 average rating, 190 reviews
Guest favorite
Room in Maitland
Stay with Fabio
Great private bedroom and bath in Maitland
Apr 8 – 13
4.9 out of 5 average rating, 59 reviews