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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, 250 reviews
Guest favorite
Home in Winter Park
Charming Retreat In Winter Park
4 beds
Apr 27 – May 2
4.95 out of 5 average rating, 22 reviews
Guest favorite
Bungalow in Winter Park
Cozy 2/2 Bungalow - Downtown Winterpark/Orlando
2 queen beds
Apr 29 – May 4
4.98 out of 5 average rating, 231 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
Home in Maitland
The Butterfly Bungalow near Park Ave
2 beds
May 12 – 17
4.96 out of 5 average rating, 113 reviews
Guest favorite
Apartment in Winter Park
The Lake House
2 beds
May 25 – 30
4.88 out of 5 average rating, 32 reviews
Guest favorite
Tiny home in Winter Park
Comfy Tiny Home @WP. Large Private Deck+Queen bed
2 beds
Apr 21 – 26
4.89 out of 5 average rating, 18 reviews
Superhost
Guesthouse in Winter Park
Tiny Cottage - 3 MI to Downtwn w/ Grill & Hammocks
1 queen bed
May 29 – Jun 3
4.92 out of 5 average rating, 266 reviews
Guest favorite
Room in Winter Park
Stay with Maria
Top Floor French Style Studio.
May 7 – 12
4.98 out of 5 average rating, 64 reviews
Superhost
Apartment in Maitland
At Mine | King Suite In North Orlando
1 king bed
Apr 21 – 26
4.76 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 30 – May 5
4.95 out of 5 average rating, 341 reviews
Guest favorite
Home in Winter Park
Modern, Quiet & Cozy - Entire house /Winter park
2 beds
Apr 28 – May 3
4.93 out of 5 average rating, 107 reviews
Guest favorite
Room in Winter Park
Stay with AdamAerospace engineer,
Pura Vida Home 1
Oct 9 – 14
4.93 out of 5 average rating, 264 reviews
Guest favorite
Home in Winter Park
Cozy Winter Park Cottage
7 beds
May 26 – 31
5.0 out of 5 average rating, 20 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
Guest favorite
Home in Winter Park
Modern 4 Bed Home in Winter Park (FullSail/UCF)
4 queen beds
Apr 18 – 23
4.85 out of 5 average rating, 101 reviews
Guest favorite
Guesthouse in Orlando
New Mid Century-Modern Studio
1 bed
Jun 14 – 19
4.95 out of 5 average rating, 38 reviews
Guest favorite
Bungalow in Orlando
Cozy Cottage in College Park.
1 queen bed
Jun 15 – 20
5.0 out of 5 average rating, 23 reviews