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Search results; Over 1,000 places in Winter Park

Superhost
Flat in Maitland
At Mine | Elegant Double Suite in North Orlando
2 double beds
21–26 Apr
4.82 out of 5 average rating, 250 reviews
Guest favourite
Home in Winter Park
Charming Retreat In Winter Park
4 beds
27 Apr – 2 May
4.95 out of 5 average rating, 22 reviews
Superhost
Flat in Maitland
At Mine | King Suite In North Orlando
1 king bed
21–26 Apr
4.76 out of 5 average rating, 106 reviews
Guest favourite
Bungalow in Winter Park
Cozy 2/2 Bungalow - Downtown Winterpark/Orlando
2 queen beds
29 Apr – 4 May
4.98 out of 5 average rating, 231 reviews
Superhost
Home in Winter Park
ꜱʟᴇᴇᴘꜱ 4, ᴡɪɴᴛᴇʀ ᴘᴀʀᴋ & ᴅᴏᴡɴᴛᴏᴡɴ
2 beds
22–27 Apr
4.9 out of 5 average rating, 41 reviews
Guest favourite
Guest house in Orlando
Comfy Studio Guest Suite
1 queen bed
4–9 May
4.91 out of 5 average rating, 55 reviews
Guest favourite
Bungalow in Orlando
Cozy Cottage in College Park.
1 queen bed
15–20 Jun
5.0 out of 5 average rating, 23 reviews
Superhost
Room in Orlando
Stay with StefanHealthcare director,
College Park Private Master Room
18–25 Apr
New place to stay
Guest favourite
Home in Winter Park
Stylish newly updated home in Winter Park
4 beds
17–22 May
5.0 out of 5 average rating, 56 reviews
Superhost
Home in Winter Park
𝕊𝕝𝕖𝕖𝕡𝕤 𝟠| 𝕎𝕚𝕟𝕥𝕖𝕣 ℙ𝕒𝕣𝕜|ᴏʀʟᴀɴᴅᴏ
4 beds
26 Apr – 1 May
4.9 out of 5 average rating, 68 reviews
Guest favourite
Home in Maitland
The Butterfly Bungalow near Park Ave
2 beds
12–17 May
4.96 out of 5 average rating, 113 reviews
Guest favourite
Guest house in Orlando
New Mid Century-Modern Studio
1 bed
14–19 Jun
4.95 out of 5 average rating, 38 reviews
Superhost
Home in Winter Park
Winter Park - Cozy retreat near Lake Killarney
3 beds
20–25 Apr
4.82 out of 5 average rating, 17 reviews
Home in Orlando
Casa Lago - Downtown Orlando
8 beds
12–17 May
New place to stay
Guest favourite
Townhouse in Orlando
★Modern DT Home★King Bed☀️Patios✔Long Stays⚡️WiFi★
3 beds
21–26 Apr
4.95 out of 5 average rating, 141 reviews
Superhost
Home in Orlando
Luxury 3BD in Downtown Orlando
3 queen beds
28 Apr – 3 May
4.82 out of 5 average rating, 17 reviews
Guest favourite
Guest house in Orlando
Amazing place in exclusive area Downtown Orlando
1 queen bed
6–11 May
4.93 out of 5 average rating, 44 reviews
Superhost
Home in Orlando
Stunning Orlando Getaway w/Spa & Heated Pool
6 beds
24–29 Apr
4.92 out of 5 average rating, 76 reviews