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Search results; Over 1,000 places in Winter Park

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
Home in Winter Park
Tiny Home - 3 MI to Downtown & Winter Park
2 queen beds
May 26 – 31
4.95 out of 5 average rating, 65 reviews
Guest favorite
Townhouse in Casselberry
Gorgeous Lake Howell Townhouse
Jun 3 – 8
4.94 out of 5 average rating, 16 reviews
Guest favorite
Guesthouse in Orlando
Amazing place in exclusive area Downtown Orlando
1 queen bed
May 6 – 11
4.93 out of 5 average rating, 44 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
Guesthouse in Orlando
Livingston Pool House- In The Heart of Downtown
2 beds
Sep 3 – 8
4.99 out of 5 average rating, 197 reviews
Guest favorite
Guest suite in Winter Park
Atmospheric Studio in the Garden
1 queen bed
Jun 9 – 14
4.96 out of 5 average rating, 245 reviews
Guest favorite
Guesthouse in Maitland
Chez Bienvenu
2 beds
Jun 3 – 8
4.87 out of 5 average rating, 381 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, 265 reviews
Superhost
Home in Maitland
Bonheur Ala Maison - Boasts beauty comfort extras
4 beds
May 28 – Jun 2
4.82 out of 5 average rating, 85 reviews
Guest favorite
Guest suite in Orlando
A SUITE RETREAT with a Garden View in the City
1 queen bed
May 11 – 16
4.98 out of 5 average rating, 300 reviews
Guest favorite
Guesthouse in Orlando
Luxury studio with lake view!
1 bed
May 11 – 16
4.99 out of 5 average rating, 75 reviews
Guest favorite
Home in Winter Park
Cheerful 3 bedroom with a spacious shaded yard
15 beds
May 4 – 9
4.93 out of 5 average rating, 60 reviews
Guest favorite
Home in Orlando
Luxe House
3 beds
Jun 10 – 15
4.98 out of 5 average rating, 48 reviews
Superhost
Home in Winter Park
𝕊𝕝𝕖𝕖𝕡𝕤 𝟠| 𝕎𝕚𝕟𝕥𝕖𝕣 ℙ𝕒𝕣𝕜|ᴏʀʟᴀɴᴅᴏ
4 beds
Apr 26 – May 1
4.9 out of 5 average rating, 69 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
Home in Orlando
Casa Lago - Downtown Orlando
8 beds
May 12 – 17
New place to stay
Superhost
Apartment in Maitland
At Mine | Spacious Double Suite in Orlando
2 double beds
Apr 21 – 26
4.8 out of 5 average rating, 174 reviews