Historic Key West Vacation Rentals

09/06/2026

One of the biggest days of our festival has arrived! Be sure to check out the full schedule and get ready to dance with us on Duval for this afternoon's Second Line Parade celebrating Jimmy Buffett! 🎶

Sunday, September 6th

Margaritaville Beach House Brunch | 7:30am to 1:30pm
Margaritaville Beach House

Bubbles Brunch Sail with Will & Jessica | 10am to Noon
Argo Navis
(Sold Out)

Meet the Author - Jimmy Buffett: A Little Golden Book Biography by Donna Rocco | 11am to 1pm
Books & Books @ Studios of Key West

Friends of Bubba Festival HQ | 11am to 4pm
Key West First Legal Rum

Chart Room Daily Hangout Headquarters | Noon to Midnight
Pier House Resort & Spa

A Pirate Looks Back: Jimmy Buffett Tribute Show | 12:30pm to 2pm
Comedy Key West
(Tickets Available)

Pool Party at the Marker | 1pm to 4pm
The Marker Key West Resort

Roger Bartlett | 1pm to 3pm
The Key West Empourium
(Sold Out)

Tales from the Chart Room | 1:15pm to 1:45pm
Pier House Resort & Spa

Wheeland Brothers FREE Concert | 2:30pm to 4pm
Sunset Pier ~ Key West

Second Line Memorial Walking Parade | 5pm to 6pm
Step off at the corner of Greene and Duval Street at 5pm

Party In The Park: Tribute to Bubba | 6pm to 10pm
Truman Waterfront Park

Key West Artisan Market at the Party in the Park | 6pm to 10pm
Truman Waterfront Park

Bubba's Official Afterparty | 10pm to Midnight
American Legion Post 168

For the full schedule and tickets, visit www.justafewfriendskeywest.com/sun-events

📸 by Nick Doll

09/06/2026

Dishes like ropa vieja and mojo-infused roast pork top the menu at multiple island eateries, and scores of Key West residents start their day with sweet café con leche or a tiny bucci, loosely translated as highly caffeinated Cuban espresso.

Some days, however, the energy jolt delivered by a morning bucci just isn’t enough — which explains the popularity of the espresso martini at local hotspots like the Key West Cooking Show’s Bar 1. While the caffeinated cocktail didn’t originate on the island, it was quickly embraced by savvy bartenders and patrons who needed a happy-hour boost.
https://keysweekly.com/42/whats-cooking-key-west-cuban-coffee-adds-zest-to-caffeinated-martinis/

09/05/2026

Dream Kitchen | Heated Saline Pool | Ultimate Privacy

Love to cook—or simply reheat your favorite takeout? Either way, you’ll love the breathtaking chef’s kitchen at California Dreaming. Stainless-steel appliances, stunning custom cabinetry, and gleaming quartzite countertops create a sophisticated space that’s as beautiful as it is functional.

The showpiece is the six-burner Italian Bertazzoni slide-in range with griddle, beautifully framed by elegant wall sconces and a custom hood. A farmhouse sink sits beneath a sun-filled window, while the expansive contrasting island offers generous prep space and comfortable seating for gathering with family and friends.

Just beyond the kitchen, sliders open to your private heated saline pool—a secluded outdoor oasis surrounded by newly landscaped grounds. Stretch out on the loungers, fire up the propane grill, and enjoy the privacy and tranquility of your own luxurious retreat.

California Dreaming — Monthly Rental. Reserve November 2026.
Link in the first comment to reserve your stay!

Historic Key West Vacation Rentals • Locally Owned, Locally Managed • Old Town · Truman Annex · Historic Seaport historickeywestvacationrentals.com

09/05/2026

09/05/2026

Escape to Key West and stay just minutes from historic Duval Street at this conveniently located duplex retreat. With off-street parking, a charming treetop view, and space to spread out, it’s an ideal choice for families or friends traveling together.

Enjoy all the fun and energy of Old Town, then come home to a quieter retreat of your own. The duplex layout offers the perfect balance of together time and personal space, making it easy for everyone to relax, recharge, and enjoy the best of Key West.

Link in first comment. Historic Key West Vacation Rentals • Locally Owned, Locally Managed • Old Town · Truman Annex · Historic Seaport historickeywestvacationrentals.com

09/05/2026

Next time you’re strolling along Higgs Beach, pause for a moment and look down at the sand. You may spot one of Key West’s most resilient little treasures: railroad vine (Ipomoea pes-caprae), also known as beach morning glory or bayhops.

A little flower thriving in harsh, sandy conditions—and still choosing to bloom brightly.

Now that feels like an affirmation worth remembering.

Historic Key West Vacation Rentals • Locally Owned, Locally Managed • Old Town · Truman Annex · Historic Seaport historickeywestvacationrentals.com

09/04/2026

Whether you’re enjoying a leisurely morning from the elegant covered front porch or retreating to your private rear oasis to bask in the Key West sunshine, Hello Gorgeous offers an effortlessly luxurious escape in the heart of Old Town. Surrounded by the charm and character of historic Key West, this beautiful retreat blends privacy, comfort, and timeless island style—creating the perfect setting for an unforgettable getaway.

Link in the first comment with availability for January-March 2027.

Historic Key West Vacation Rentals • Locally Owned, Locally Managed • Old Town · Truman Annex · Historic Seaport historickeywestvacationrentals.com

09/04/2026

09/04/2026

Villa Josine makes a memorable first impression with its undeniable curb appeal and classic Key West charm. A stunning example of a traditional Key West eyebrow house, this distinctive architectural style became popular in the 1800s, with its extended roofline helping keep the second story naturally cooler long before the advent of air conditioning.

While Villa Josine celebrates the character and history of Old Key West, the home itself has been completely renovated for modern island living. High-end designer finishes and updated amenities blend seamlessly with its historic architecture, creating a stylish and comfortable retreat with plenty of room for the entire family to relax, reconnect, and enjoy paradise together.

Link in first comment to reserve Villa Josine for your fall vacations and celebrations, including Goombay Festival and Fantasy Fest.

Historic Key West Vacation Rentals • Locally Owned, Locally Managed • Old Town · Truman Annex · Historic Seaport historickeywestvacationrentals.com