Experience the Key West Songwriters Festival

The Key West Songwriters Festival returns in 2023! Don’t miss your chance to experience amazing live performances, indulge and imbibe at the local eateries and bars, and experience spring in Key West! We at Key West Vacation Homes are thrilled to serve as a Platinum Sponsor for the festival as it’s one of our favorites that Key West presents! Check out our rental availability for the festival here.

With over 200+ artists and 60+ free shows, the Key West Songwriters Festival is the can’t-miss event of the year! Taking place May 3rd through the 8th in Key West’s best venues and favorite watering holes, festival goers will hear the stories behind country music’s biggest hits. In its 27th year, the Key West Songwriters Festival is the largest festival of its kind.

Three-time CMT award winner Jelly Roll headlines the festival at the Key West Amphitheater on May 5th. Receive $10 off your ticket when you use code KWVACATIONHOMES10. Tickets can be purchased at thekeywestamp.com.

In addition to Jelly Roll, the 2023 lineup includes three-time Grammy Award nominee Elle King, country pop notable Mitchell Tenpenny, renowned Southern writer Rivers Rutherford, prolific chart-topper Jeffrey Steele, former Mavericks frontman Raul Malo and the songwriting super-trio dubbed the Love Junkies.

The Key West Songwriters Festival features over 60 free shows including a performance by Michael Ray on the Duval Street Stage on May 6th. The most up-to-date schedule and artist lineup can be found in the official Key West Songwriters Festival app which can be downloaded from the Apple App Store or the Google Play Store.

2023 Key West Songwriters Festival Schedule:

TUESDAY, MAY 2

9 PM – 4 PM ISLAND DOGS BAR – Come as you are!

WEDNESDAY, MAY 3

1 PM – 4 PM DANTE’S

3 PM – 5 PM WICKER GUEST HOUSE POOLSIDE

6 PM – 8:30 PM OCEAN KEY RESORT – Sunset Pier Kick Off Party Host, Storme Warren

7 PM – 10 PM CONCH REPUBLIC SEAFOOD COMPANY

8 PM SALTY FROG’S

8 PM KEY WEST THEATER – SOLD OUT

9 PM RICK’S & DURTY HARRY’S

10 PM GREEN PARROT – HD Radio Late Night Hang

THURSDAY, MAY 4

10 AM – 12 PM KEY WEST THEATER – TICKETS

12 PM – 4 PM SOUTHERNMOST BEACH RESORT – BEACH BASH

1 PM – 4 PM LA CONCHA POOL PARTY

1 PM – 10 PM RAMS HEAD SOUTHERNMOST

6 PM – 9 PM GENERAL HORSEPLAY

2 PM – 4 PM OCEAN KEY RESORT SUNSET PIER

3 PM – 6 PM DANTE’S POOL PARTY WITH DULCE VIDA

4 PM – 7 PM BLUE HEAVEN

5:30 PM – 9:30 PM SLOPPY JOE’S

4 PM – 5:30 PM BOSE BACKSTAGE LISTENING ROOM – TICKETS

4 PM – 7 PM KEY WEST THEATER – SOLD OUT

5 PM – 7 PM THE MARKER RESORT POOL PARTY

6 PM – 8:30 PM CAPITANA RESORT BEACH SHOW

6 PM – 8 PM FURY SONGWRITERS SAIL – TICKETS

6:30 PM – 10:30 PM SCHOONER WHARF BAR

7:30 PM – 10:30 PM SUNSET GREEN at 24 NORTH – TICKETS

8 PM – 11:30 PM KEY WEST THEATER – SOLD OUT – BMI @ The Blue Bird Show!

8 PM – 11PM SAN CARLOS INSTITUTE – TICKETS – Texas Heritage Songwriters Association

10 PM – 1AM THE BACKYARD at 618 DUVAL

10 PM GENERAL HORSEPLAY – HD Radio Late Night Hang

10 PM – 1 AM MARGARITAVILLE CAFÉ

12 AM – 2 AM GREEN PARROT – Texas Heritage After Party

FRIDAY, MAY 5

10 AM – 12 PM KEY WEST THEATER – TICKETS – Bloody Mary Bash

11AM – 2 PM MARRIOTT BEACHSIDE RESORT POOLSIDE

12 PM – 3 PM HYATT CENTRIC KEY WEST RESORT BLUE MOJITO

12 PM – 4 PM SOUTHERNMOST RESORT PINEAPPLE POOL PARTY

1 PM – 10 PM RAMS HEAD SOUTHERNMOST

1 PM – 4 PM WICKER GUEST HOUSE POOLSIDE

2 PM – 4 PM OCEAN KEY RESORT SUNSET PIER

3 PM – 6 PM SOUTHERNMOST HOUSE HOTEL

3 PM – 6 PM LIGHTHOUSE COURT – KIMPTON

5 PM – 8 PM THE PERRY HOTEL & MARINA EVENT LAWN

5 PM – 8 PM KEY WEST THEATER – TICKETS

5:30 PM – 9:30 PM SLOPPY JOE’S

5:30 PM – 7 PM GREEN PARROT SOUND CHECK

8 PM – 11 PM SAN CARLOS INSTITUTE – TICKETS

7 PM – 10 PM THE KEY WEST AMPTHITHEATER – TICKETS – Hosted by Storme Warren

10 PM – 1 PM MARY ELLENS

10 PM – 1 AM IRISH KEVIN’S

10 PM – 2 AM GREEN PARROT

10 PM THE BACKYARD at 618 DUVAL – HD Radio Late Night Hang

SATURDAY, MAY 6

11 AM – 1 PM SOUTHERNMOST BEACH PAVILION – TICKETS – Mimosa Meet & Greet

11 AM – 2 PM HARD ROCK CAFÉ

12 PM – 3 PM THE MARKER RESORT POOL PARTY

2 PM – 5 PM THE PERRY HOTEL & MARINA

1 PM – 4 PM KIMPTON WINSLOW’S BUNGALOWS

1 PM – 10 PM RAMS HEAD SOUTHERNMOST

2 PM – 4 PM OCEAN KEY RESORT SUNSET PIER

3 PM – 6 PM RICK’s & DURTY

2 PM – 5 PM OCEANS EDGE POOL PARTY

4 PM – 6 PM WINE O at LA CONCHA HOTEL

4 PM – 6 PM CURRY MANSION INN

6 PM – 8 PM FURY SUNSET SAIL – SOLD OUT

7 PM – 10 PM DUVAL STREET STAGE Hosted by Storme Warren

8 PM – 11 PM THE KEY WEST THEATER – TICKETS

10pm – ISLAND DOGS BAR – Island Revival Roadshow

10 PM – 1 AM ROCK HOUSE LIVE

10 PM – MARYELLENS

10 PM – GENERAL HORSEPLAY

SUNDAY, MAY 7

12 PM – 3 PM SOUTHERNMOST BEACH

12 PM – 4:45 PM SLOPPY JOE’S

2 PM – 6 PM RAMS HEAD SOUTHERNMOST

1 PM – 4 PM GATES HOTEL – Sunday Fun-Day Pool Party

3 PM – 6 PM SOUTHERNMOST HOUSE HOTEL 8 PM

8 PM KEY WEST THEATER – TICKETS – All-Star Encore

Stay with Key West Vacation Homes

Whether you prefer a cozy condo in the heart of Old Town or one of our luxurious waterfront Key West rentals with breathtaking views, our Key West vacation homes provide a tranquil and private escape after a day of exploring the island’s attractions. With a variety of vacation homes in Key West, Florida, you can find the perfect retreat to complement your Key West itinerary. Enjoy the freedom and flexibility that comes with having your own space, allowing you to relax and recharge in between your Key West adventures.