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North Orange Avenue
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Search results; Over 1,000 places in Winter Park
Over 1,000 places in Winter Park
Superhost
Superhost
Home in Winter Park
Charming home @wp. Patio +Gazebo. close to highwys
6 beds
6 beds
Apr 2 – 7
Apr 2 – 7
$123
night
$123 per night
4.67 out of 5 average rating, 18 reviews
4.67 (18)
Superhost
Superhost
Apartment in Maitland
At Mine | Double Suite in Orlando
2 double beds
2 double beds
Apr 1 – 6
Apr 1 – 6
$91
$50
night
$50 per night, originally $91
4.82 out of 5 average rating, 169 reviews
4.82 (169)
Guest favorite
Guest favorite
Home in Orlando
Cheerful 4-bedroom with large and lush back yard.
5 beds
5 beds
Apr 6 – 11
Apr 6 – 11
$191
night
$191 per night
4.87 out of 5 average rating, 47 reviews
4.87 (47)
Guest favorite
Guest favorite
Home in Winter Park
Tiny Home - 3 MI to Downtown & Winter Park
2 queen beds
2 queen beds
Apr 14 – 19
Apr 14 – 19
$112
$90
night
$90 per night, originally $112
4.95 out of 5 average rating, 61 reviews
4.95 (61)
Guest favorite
Guest favorite
Guesthouse in Orlando
Amazing place in exclusive area Downtown Orlando
1 queen bed
1 queen bed
Apr 2 – 7
Apr 2 – 7
$97
$80
night
$80 per night, originally $97
4.93 out of 5 average rating, 44 reviews
4.93 (44)
Superhost
Superhost
Home in Winter Park
Mills House @WP. Sleeps 11 Renovated. Queen beds
6 beds
6 beds
Apr 14 – 19
Apr 14 – 19
$184
$147
night
$147 per night, originally $184
4.84 out of 5 average rating, 85 reviews
4.84 (85)
Guest favorite
Guest favorite
Guesthouse in Orlando
New Mid Century-Modern Studio
1 bed
1 bed
May 24 – 29
May 24 – 29
$85
night
$85 per night
4.96 out of 5 average rating, 24 reviews
4.96 (24)
Guest favorite
Guest favorite
Bungalow in Winter Park
Cozy 2/2 Bungalow - Downtown Winterpark/Orlando
2 queen beds
2 queen beds
Apr 14 – 19
Apr 14 – 19
$130
night
$130 per night
4.98 out of 5 average rating, 224 reviews
4.98 (224)
Guest favorite
Guest favorite
Apartment in Orlando
Quiet Shed in Downtown
1 queen bed
1 queen bed
Apr 5 – 10
Apr 5 – 10
$100
$86
night
$86 per night, originally $100
4.95 out of 5 average rating, 613 reviews
4.95 (613)
Guest favorite
Guest favorite
Home in Orlando
Yale House in College Park 2 mi from Downtown
2 beds
2 beds
Apr 1 – 6
Apr 1 – 6
$161
night
$161 per night
4.92 out of 5 average rating, 53 reviews
4.92 (53)
Guest favorite
Guest favorite
Home in Winter Park
Stylish newly updated home in Winter Park
4 beds
4 beds
Apr 8 – 13
Apr 8 – 13
$176
night
$176 per night
5.0 out of 5 average rating, 48 reviews
5.0 (48)
Guest favorite
Guest favorite
Home in Winter Park
Cozy Winter Park Home
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
$187
$157
night
$157 per night, originally $187
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Guest favorite
Guest favorite
Home in Orlando
Colonialtown Bungalow
2 beds
2 beds
Apr 7 – 12
Apr 7 – 12
$163
night
$163 per night
4.91 out of 5 average rating, 11 reviews
4.91 (11)
Superhost
Superhost
Villa in Winter Park
As close as you can stay to Rollins College!
2 beds
2 beds
Apr 1 – 6
Apr 1 – 6
$345
$283
night
$283 per night, originally $345
4.91 out of 5 average rating, 34 reviews
4.91 (34)
Guest favorite
Guest favorite
Home in Orlando
Charming 2BR Cottage, Downtown Orlando
Apr 14 – 19
Apr 14 – 19
$151
$116
night
$116 per night, originally $151
4.95 out of 5 average rating, 19 reviews
4.95 (19)
Guest favorite
Guest favorite
Townhouse in Orlando
★Modern DT Home★King Bed☀️Patios✔Long Stays⚡️WiFi★
3 beds
3 beds
Apr 21 – 26
Apr 21 – 26
$181
$158
night
$158 per night, originally $181
4.95 out of 5 average rating, 138 reviews
4.95 (138)
Guest favorite
Guest favorite
Home in Winter Park
Charming Retreat In Winter Park
4 beds
4 beds
Apr 21 – 26
Apr 21 – 26
$205
$167
night
$167 per night, originally $205
4.94 out of 5 average rating, 18 reviews
4.94 (18)
Guest favorite
Guest favorite
Home in Orlando
The Villa Orlando@College Park. Sleeps16.
7 beds
7 beds
May 19 – 24
May 19 – 24
$243
night
$243 per night
4.98 out of 5 average rating, 62 reviews
4.98 (62)
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