We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Over 1,000 places in Winter Park

Guest favorite

Apartment in Winter Park

Apt D -Modern Elegance in the Heart of Winter Park

2 queen beds

Apr 26 – May 1

$91 per night, originally $104

4.96 out of 5 average rating, 214 reviews

Guest favorite

Home in Winter Park

Relax on a private lake in Winter Park!

2 beds

Apr 20 – 25

$272 per night

4.97 out of 5 average rating, 104 reviews

Guest favorite

Guesthouse in Winter Park

WELCOME HOME IN WINTER PARK

1 queen bed

Apr 20 – 25

$80 per night, originally $99

4.82 out of 5 average rating, 234 reviews

Guest favorite

Condo in Winter Park

Greatest Location in Winter Park! (2)

2 beds

Apr 28 – May 3

$270 per night

4.98 out of 5 average rating, 40 reviews

Guest favorite

Guesthouse in Winter Park

Private and Peaceful with Full Kitchen

1 queen bed

May 15 – 20

$85 per night

4.98 out of 5 average rating, 248 reviews

Villa in Winter Park

Balfour Villa

Apr 22 – 27

$155 per night, originally $199

4.75 out of 5 average rating, 75 reviews

Superhost

Condo in Winter Park

Lovely Winter Park Home close to Hospitals !

2 beds

Apr 26 – May 1

$100 per night

4.81 out of 5 average rating, 57 reviews

Guest favorite

Home in Winter Park

Cozy Winter Park Home

4 beds

Apr 23 – 28

$163 per night, originally $190

5.0 out of 5 average rating, 30 reviews

Guest favorite

Home in Maitland

The Butterfly Bungalow near Park Ave

2 beds

May 12 – 17

$125 per night, originally $145

4.96 out of 5 average rating, 113 reviews

Guest favorite

Bungalow in Winter Park

Cozy 2/2 Bungalow - Downtown Winterpark/Orlando

2 queen beds

May 3 – 8

$127 per night

4.98 out of 5 average rating, 231 reviews

Guest favorite

Apartment in Winter Park

The Lake House

2 beds

May 25 – 30

$80 per night

4.88 out of 5 average rating, 32 reviews

Guesthouse in Winter Park

Cozy guest house close to Downtown Orlando

Apr 24 – 29

$74 per night, originally $93

4.85 out of 5 average rating, 109 reviews

Guest favorite

Cottage in Winter Park

Winter Park Pearl 6 min drive to historic Park Ave

2 beds

May 7 – 12

$145 per night, originally $188

4.95 out of 5 average rating, 342 reviews

Guest favorite

Home in Winter Park

Modern, Quiet & Cozy - Entire house /Winter park

2 beds

Apr 28 – May 3

$123 per night, originally $153

4.93 out of 5 average rating, 107 reviews

Guest favorite

Guesthouse in Orlando

New Mid Century-Modern Studio

1 bed

May 24 – 29

$85 per night

4.95 out of 5 average rating, 38 reviews

Superhost

Home in Winter Park

ꜱʟᴇᴇᴘꜱ 4, ᴡɪɴᴛᴇʀ ᴘᴀʀᴋ & ᴅᴏᴡɴᴛᴏᴡɴ

2 beds

Apr 22 – 27

$113 per night, originally $139

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 20 – 25

$199 per night, originally $320

4.85 out of 5 average rating, 101 reviews

Guest favorite

Home in Winter Park

Comfy 3 Bedrooms - 2 Bathrooms home with pool.

4 beds

Apr 20 – 25

$186 per night

4.87 out of 5 average rating, 103 reviews