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  • "Live Like A Local" Key West Vacation Special

    Packages from $4,533
    Experience Key West the way it was meant to be—relaxed, adventurous, and effortlessly fun. This curated getaway includes:

    Waterfront comfort: Stay in Old Town just steps from Mallory Square with tropical views and laid-back luxury
    Island transportation: A stylish golf cart for wherever the day takes you
    Taste the island: Our favorite local spots—no chains, just real Key West flavor
    Unforgettable water adventures: From sunset sails to private island and sandbar explorations
    Immersive island experiences: Guided walking tours, local entertainment, and more

    Your island escape starts here—laid-back luxury with a local twist.
    Reserve Today More Details
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    • Accommodations
      Old Town Resort
    • Transportation
      Golf cart
      Performance Golf Cart
    • Dining
      Best Local Recommendations
    • Adventures
      Land & Sea Exploration
    Additional Package Details

    🏝️ Your Perfect Key West Escape Starts Here

    This isn’t just another vacation—it’s your VIP pass to living the Key West dream. From luxury accommodations to unforgettable adventures, every detail of this package is designed to deliver an effortless, immersive, and unforgettable island experience.

    🏨 Where You Stay Sets the Tone

    Enjoy premier waterfront accommodations just steps from world-famous Mallory Square and a block from lively Duval Street. This resort sits inside a working cruise port—placing you at the heart of Old Town. Lounge by the sparkling pool tucked into lush tropical gardens. Dine on globally-inspired cuisine with ocean views. And walk to everything: art galleries, music, nightlife, architecture, and more.

    Location, luxury, and laid-back vibes—this is island living at its finest.

    🛺 Cruise the Island Like a Local

    Ditch the rental car. You’ll get a premium 4-seater golf cart to explore every inch of the island with ease. Head to the beach, glide through charming neighborhoods, park steps from your favorite restaurant—or go on a moonlit Duval Street cruise. It’s freedom on four wheels, and it’s included.

    🍴 Let Your Tastebuds Travel Too

    We’ll guide you to the best of Key West’s culinary scene with hand-picked local dining experiences. Whether you’re craving island comfort food or refined coastal cuisine, we’ll show you where to find it—and make it unforgettable.

    🚤 Your Island Adventures Await

    ⛵ Sunset Sail – Sip fine wines and craft beers while sailing into the golden hour aboard a majestic schooner. Hors d’oeuvres and ocean breezes included.

    🛥️ Private Boat Charter – Want dolphins, snorkeling, or just floating at the sandbar with a drink in hand? It’s your call. A private charter lets you explore your way with a local captain who knows the secret spots.

    🛺 Midnight Golf Cart Expedition – After dark, the island takes on a whole new vibe. Discover Key West’s hidden corners on your own self-guided night cruise.

    🚶 Walking or Bike Tour – Get the inside scoop on Key West’s colorful past and present with a guided tour through tropical neighborhoods and historic streets. (4-night minimum)

    👻 Ghost Tour or Pub Crawl – Dive into haunted history or raise a glass at the island’s best bars. Whichever you choose, it’s unforgettable. (5-night minimum)

    💡 Good to Know:

    • Package pricing is customized based on your group size, arrival date, room type, and availability.
    • Meals & airline flights not included unless otherwise specified.

    🏝️ Don’t Just Visit Key West—Live It.

    With this all-in-one package, we’ve taken care of the planning so you can focus on soaking it all in. From sunrise to midnight, every moment is yours to own.

    📞 Call now to reserve your Key West escape: 305-290-2049
    💻 Or book online now: Reserve Your Trip Here

    Local Key West vacation experts are here to help plan the perfect getaway just for you.
    Reserve Today More Details FAQ's

Planning a Trip to Key West?

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Lexi Roberts, OKW Concierge specialist
Your Local Concierge,
Lexi Roberts

The staff at Our Key West is exceptional and know the meaning of excellent customer service.

-Del Arnold

These Folks are Super Cool!

-Annie

Their shop is dope.

-Francesca from Pittsburgh

We had such a great time on the Havana Day Trip! This is a must do on everyone's bucket list.

-Steven Michelin

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About Us

Local since 1974, we create guest experiences that emphasize the natural world, art, music, food, history, and local characters. We provide premium concierge services, and serve as market-maker for a select pre-screened portfolio of the island’s best guest activity providers. We have a commitment to the highest hospitality standard, providing personalized guest support daily from 8am to 6pm.

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Activities
  • Havana Day Trip
  • Fishing Charters
  • Golf Cart Rental
  • Boat Rental
  • Paddle the Mangroves
  • All Day Watersports Adventure
  • Dolphin Watch & Snorkel
  • Key West Bike Tour
  • Bike Rentals
  • Bike Rentals
  • Personal Chef & Catering
  • Sky Dive
  • Key West Private Boat Charter
  • Schooner Sunset Sail
  • Dry Tortugas- Ferry
  • Jet Ski Tour
  • Schooner Sunset Sail
  • Gallery Stroll & Art Tour

Contact Info

Our Key West logo

613 Simonton St
Key West, Florida 33040

(305) 290-2049

PROUD MEMBER OF

Key West Business Guild Key West Attractions Association

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