Guide to Key West

Explore the vibrant charm of Key West with our comprehensive area guide. From sun-soaked beaches and water adventures to iconic festivals and historic landmarks, this island paradise offers something for everyone. Discover the best places to eat, drink, and explore, and stay up-to-date with local events and insider tips. Whether you’re planning a family vacation, a romantic getaway, or an adventure with friends, our guide is here to help you uncover the magic of Key West. Dive into curated recommendations, expert blogs, and must-see attractions to make your trip unforgettable.

Things to Do

Explore activities like snorkeling, sunset cruises, biking through Old Town, and visiting historic landmarks.

Need Help Planning Your Trip?

Our expert concierge team is here to assist! From booking activities and tours to providing insider tips, we’ll ensure your Key West getaway is effortless and memorable. Reach out to us today to get started.

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What's happening in Key West

Stay up-to-date with Key West’s vibrant event calendar, including Fantasy Fest, Hemingway Days, and Lobsterfest.

More events

Key West Blog

Get insider tips, travel guides, and local stories to enhance your Key West experience.

From the heart of Texas to the soul of Key West: Why the Conch Republic calls to Lone Star travelers

 If everything’s bigger in Texas, then everything is bolder in Key West — from its colorful,...

Give thanks, island-style: Spend a family Thanksgiving in Key West

As the holidays approach, many of us dream about slowing down, spending quality time with loved ones, and reflecting on everything...

Why Summer and Fall Are the Perfect Time to Stay a Month in Key West

There’s something magical about a quiet Key West summer and fall. The island exhales. The streets are a little less busy. The breeze...

Key West for art lovers: A guide to the island’s creative soul

Key West is more than a sun-soaked destination — it’s a canvas. With pastel streets and colorful traditional homes, a rich literary...

Settle In. Slow Down. Live The Story.

At Historic Key West Vacation Rentals, we believe travel should be more than a getaway. It should be a connection — to a place, a past, and a way of life that invites...

Fall family fun in Key West: The best island delights for kids this season

After the summer crush, many vacation destinations wind down in the fall, but Key West comes alive — with sunny skies,...

Fall in love with paradise: Why the off-season could be the best season in Key West

When most travelers think of a Florida getaway, they picture the high-energy winter season or spring break crowds. But savvy...

Experience the Magic of Fantasy Fest 2025 with Historic Key West Vacation Rentals

The fall in Key West brings vibrant energy, cooler breezes, and the island’s most anticipated event — Fantasy...

Book your Key West winter escape now and work from paradise for a month

Each year when the snow begins to fall and daylight disappears before dinner, there are those who wistfully dream of warm ocean breezes,...

In laid-back Key West, relaxation is a way of life! Here are the best ways to unwind this August

If you’re planning an August vacation to Key West, get ready to embrace the island’s easygoing...

Enduring Craft: The Architectural and Cultural Legacy of a Cigar Maker’s Cottage in Key West

In Old Town Key West, where sun-faded porches meet storied streets, one cottage stands as a rare and powerful...

Regular life is no day at the beach! Plan your August escape to Key West

  Dreaming of sun, sand and sea this August? Look no further than fabulous Key West! The ultimate tropical getaway, Key West makes...

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