Mark Your Calendar

From fishing strolls and harbor walks to bustling parties and live music, The Perry Hotel offers eclectic opportunities for mingling, celebrating, and simply enjoying life. Get out there and explore the many events happening right here.

Woman inside at the edge of pool smiling

Songwriters Festival

Friday, May 10 | 3-5PM

The Key West Songwriters Festival is coming to The Perry on May 10th! Chill poolside with live performances by talented songwriters, then take advantage of our shuttle service and enjoy performances all over the island as part of this renowned Key West fest. 

3:00pm - Johnny Dibb, John Gurney
4:00pm - Barrett Baber, Blue Foley, Larry Fleet

Book your stay now and enjoy the concert from the comfort of your very own private balcony!

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Sip and Shop at Green Pineapple

Friday, May 10 | 5:00–8pm

Join us at the Green Pineapple for another amazing sip & shop directly following the performance at the pool for the Key West Songwriters Festival. We'll be featuring complimentary champagne, live music, and incredible merchandise from a variety of local vendors, such as ZEN by Karen Moore Jewelry, Made by Soto Jewelry, Fresha London Clothing, and more!



SUNDAY, MAY 12 | 10:30AM - 2PM

Over the years, your mom has spared no expense to take care of you. This Mother’s Day, thank her for what she’s done with a waterfront brunch at Matt’s Stock Island Kitchen & Bar. Treat her to three buffets and unlimited small plates, as well as unlimited bloody marys and mimosas, from 10:30am to 2pm. Make your reservation today!

Adults | $65
Children | $25

Glass of bear on a coaster on a wooden table


Saturday, May 25 | 6-8pm

Join us at Matt's Stock Island Kitchen & Bar for happy hour from 6–8pm, plus a silent auction, featuring gift baskets, gift certificates, vacations, and more! All proceeds from the silent auction and a percentage of every South Beach Blood Orange IPA purchased will be donated to The Domestic Abuse Shelter of the Florida Keys.

Perry Offer Matt Brunch


Every Sunday

Sundays are fun days with brunch at Matt’s Stock Island Kitchen & Bar. Enjoy three buffets and unlimited small plates, as well as unlimited bloody marys and mimosas, every Sunday from 10:30am to 2pm. Make your reservation today!

Adults | $55
Children | $20

top level view of a grilled chicken dinner with 2 glasses of beer and fries on the side



Every Wednesday, Matt's Stock Island Kitchen & Bar presents a Family Fried Chicken Night with all the fixings. For just $15 per person, you and your family can indulge in cornbread mash, citrus coleslaw, roasted corn on the cob, and—of course—plenty of fried chicken!

Perry Offer LiveMusic


Every Friday & Saturday from 6-8pm

Enjoy live music poolside at the Matt's Stock Island Kitchen & Bar every Thursday, Friday, Saturday from 6pm to 8pm, and our new weekly Sunday Brunch from 10:30-2pm, from our talented local musicians including:

  • Drew Gunning
  • Tim Hollohan
Perry Offer HappyHour

Salty Oyster Bar’s
Daily Happy Hour

Daily 4-6PM

Everyday from 4pm to 6pm, Salty Oyster Bar is serving up a legendary happy hour, including 50% off select food and premium beverages. And don't forget about live music every Friday & Saturday at Matt's, just across the pool!

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Daily 6-8pm

Enjoy $3 oysters and specialty beer, 50% off signature wine, $5 select cocktails, and even $5 tasty tapas at Matt's Stock Island Kitchen & Bar during the 6pm to 8pm happy hour. Eat, drink and be merry with us every day of the week.

Birds on the beach

Design Your Own Event

Looking to host your own fantastic gathering at The Perry? Whether you're interested in hosting a professional business meeting or a lively wedding party, allow us to help you in planning something memorable.

Start Planning


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