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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 21 – 26
4.82 out of 5 average rating, 251 reviews
Guest favorite
Home in Winter Park
Modern 4 Bed Home in Winter Park (FullSail/UCF)
4 queen beds
Apr 20 – 25
4.85 out of 5 average rating, 101 reviews
Home in Winter Park
Updated 3/2 home in Winter Park!
3 beds
Apr 21 – 26
4.75 out of 5 average rating, 4 reviews
Guest favorite
Apartment in Winter Park
Apt D -Modern Elegance in the Heart of Winter Park
2 queen beds
Apr 26 – May 1
4.96 out of 5 average rating, 214 reviews
Guest favorite
Guesthouse in Winter Park
Private and Peaceful with Full Kitchen
1 queen bed
May 15 – 20
4.98 out of 5 average rating, 248 reviews
Guest favorite
Home in Maitland
The Butterfly Bungalow near Park Ave
2 beds
May 12 – 17
4.96 out of 5 average rating, 114 reviews
Guest favorite
Home in Winter Park
Guest Suite in Winter Park/Orlando
1 queen bed
Apr 21 – 26
4.9 out of 5 average rating, 129 reviews
Superhost
Home in Winter Park
ꜱʟᴇᴇᴘꜱ 4, ᴡɪɴᴛᴇʀ ᴘᴀʀᴋ & ᴅᴏᴡɴᴛᴏᴡɴ
2 beds
Apr 22 – 27
4.9 out of 5 average rating, 41 reviews
Superhost
Condo in Winter Park
Lovely Winter Park Home close to Hospitals !
2 beds
Apr 26 – May 1
4.81 out of 5 average rating, 57 reviews
Guest favorite
Guesthouse in Orlando
New Mid Century-Modern Studio
1 bed
May 24 – 29
4.95 out of 5 average rating, 38 reviews
Guest favorite
Home in Winter Park
Charming Retreat In Winter Park
4 beds
May 13 – 18
4.95 out of 5 average rating, 22 reviews
Guest favorite
Cottage in Winter Park
Winter Park Pearl 6 min drive to historic Park Ave
2 beds
May 7 – 12
4.95 out of 5 average rating, 342 reviews
Guest favorite
Home in Winter Park
Cheerful and stylish 2-bedroom with parking
3 beds
Apr 22 – 27
4.94 out of 5 average rating, 16 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, 141 reviews
Guest favorite
Home in Orlando
Colonialtown Bungalow
2 beds
May 19 – 24
4.93 out of 5 average rating, 15 reviews
Guest favorite
Cottage in Orlando
Luxury Container Home-hot tub-30 min to Disney
3 beds
Apr 22 – 27
4.94 out of 5 average rating, 78 reviews
Guest favorite
Bungalow in Orlando
King/Queen Bungalow w/ porch | central vibey area
3 beds
Jun 14 – 19
4.99 out of 5 average rating, 78 reviews
Guest favorite
Home in Casselberry
Spacious 3 BR Home Perfect for Orlando Getaway
1 queen bed
May 12 – 17
5.0 out of 5 average rating, 42 reviews