From unforgettable adventures and world-class dining to transportation and special celebrations, our local experts are here to create a seamless, personalized experience from arrival to departure.
Choose a category below, or use our concierge survey and let us curate the perfect Key West stay around you.
Easy, reliable ways to get around Key West and the Florida Keys.
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Snorkeling, sandbars, jet skis, dolphins, diving, kayaking, boat rentals and private charters.
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From offshore trophy fishing to relaxed local backcountry trips.
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Sails, cruises, tiki boats and other ways to experience Key West at sunset.
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Handpicked dining, live shows and Key West nightlife for every taste and occasion.
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Local favorites, live sets and offers worth discovering.
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Discover Key West history, food, legends and landmarks.
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Relax, recharge and feel your best while you are in Key West.
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Pre-arrival conveniences, vacation-home extras, celebrations and special requests.
Explore →Snorkeling, sandbars, jet skis, dolphins, diving, kayaking, boat rentals and private charters.
Explore vibrant reefs and marine life in crystal-clear Key West waters.
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Relax, swim and soak up the sun at beautiful shallow-water sandbars.
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High-speed water fun and breathtaking aerial views.
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See dolphins in their natural habitat and pair it with time in the water.
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Discover coral reefs, wrecks and underwater Key West.
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Paddle mangroves, backwaters and night-time waterways.
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Choose a boat that fits your group and your day on the water.
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Build a private day around your group, interests and schedule.
Explore options →From offshore trophy fishing to relaxed local backcountry trips.
Venture beyond the reef for big-game action and trophy catches.
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Stay close to shore for productive fishing and a wide variety of species.
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Explore quiet shallows, flats, mangroves and hidden backcountry.
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Affordable shared trips that are great for families and first-time anglers.
Explore options →Sails, cruises, tiki boats and other ways to experience Key West at sunset.
Spacious, stable and social sunset sailing.
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Historic vessels, traditional sailing and timeless Key West charm.
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Local music, tropical drinks and sunset on the water.
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Private sailing experiences built around your group and occasion.
Explore options →Handpicked dining, live shows and Key West nightlife for every taste and occasion.
Start the day with cafés, brunch favorites and waterfront mornings.
Explore options →Cabaret, drag shows, live performances, lounges and vibrant Key West nights.
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Concierge-approved spots loved by locals and repeat visitors.
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Intimate settings for anniversaries, proposals and special evenings.
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Chef-driven, elevated dining and premium service.
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Dinner with live entertainment and island atmosphere.
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Private rooms, group tables and special-occasion dining.
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Relaxed restaurants with options for all ages.
Explore options →Easy, reliable ways to get around Key West and the Florida Keys.
Street-legal carts in multiple sizes for convenient island transportation.
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Single- and two-seat scooter rentals for quick island travel.
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Cruisers, kids bikes, mountain bikes, e-bikes and fitness bikes.
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Airport transfers, passenger vans and custom Up the Keys tours.
Explore options →Discover Key West history, food, legends and landmarks.
Two classic ways to discover the island.
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Guided rides through island streets and local stories.
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Taste your way through Key West with local guides.
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Haunted history and local legends after dark.
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Explore at your own pace with a curated route.
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Art, history, maritime heritage and the Key West Custom House.
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Private access, distinctive settings and memorable experiences curated by your concierge.
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Explore beyond Key West with curated Florida Keys day trips.
Explore options →Relax, recharge and feel your best while you are in Key West.
Beachfront, private and group yoga experiences.
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Healthy dining, meal delivery and nutrition-minded options.
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In-villa, couples, prenatal, sports and relaxation massage.
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Facials, body treatments, manicures, pedicures and spa packages.
Explore options →From a stocked kitchen before arrival to celebrations, family gear and unusual requests, let your concierge take care of the details.
Arrive to groceries already placed in the refrigerator, freezer and cupboards.
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Water, coffee, soft drinks, mixers and other requested refreshments.
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Cribs, high chairs, strollers and useful family equipment.
Explore options →Coolers, chairs, umbrellas, wagons and other vacation essentials.
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Cornhole, yard games, board games and more fun for the whole family.
Explore options →Enjoy a memorable meal without leaving your vacation home.
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Custom cakes delivered and ready for the celebration.
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Birthdays, anniversaries, proposals, welcome surprises and more.
Explore options →Christmas trees, seasonal decorations and holiday touches.
Explore options →Flowers, treats and thoughtful details waiting when you arrive.
Explore options →Beds, bowls, treats and useful supplies for four-legged guests.
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Have something unusual in mind? Ask us and we'll see what we can arrange.
Ask your concierge →Tell us what sounds good and our local experts will help you narrow the options.
Talk to Your ConciergeTake our short survey and let us create a personalized itinerary just for you.
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