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The Best Key West Getaway

5 to 7+ Nights from $1,656*
* Sample price: priced within the past 7 days for a 2/3/2026 arrival, departing Washington WAS (All Airports)(DC), US. Choose departure city, cabin and dates.

Customize and Book

Add Outbound & Return Flights

This 5 night sample itinerary includes:

  • Flight into and out of Key West
  • Hotel for 5 nights in Key West

    Sample of Included Tours:
  • Guided City Tour
  • Daytime Sailing and Watersport Adventure Excursion
  • Ghost and Mysteries Tour
  • Sunset Cruise Experience

    Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.

An epic vacation at one of Florida`s best cities!. Get ready to enjoy Key West (island city that is part of the Florida Keys archipelago, known for its coral reefs, famous for watersports, lively nightlife and beaches): from visit multiple locations and learn about the spooky histories and haunted happenings from your guide, to enjoy the sunset from the water on cruise, to sailing adventure and water sports like kayaking, snorkeling, parasailing and more....there is no way to be bored!.

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Flexible Itinerary

  • Key West, FL

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USA

Customer Reviews

Trip Summary

  • Key West, FL
    Key West, FL

    At the end of the 113-mile Overseas Highway in the Florida Keys is the vibrant town of Key West, the southernmost point in the continental United States. The `Conch Republic`, just 90 miles from Cuba, has a flair and attitude all its own, which you can see out on Duval Street and Mallory Square, places to see and be seen. Grab a cold drink and enjoy the relaxing and welcoming tropical atmosphere only Key West knows how to provide.

    Visit and discover the Ernest Hemingway House and Museum, Southernmost Point Marker, Mallory Square, Duval Street, Fort Zachary Taylor, Smathers Beach, Truman Little White House, Key West Lighthouse, Key West Aquarium, Key West Butterfly and Nature Conservatory, and so much more!

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