Florida Keys Vacation Packages

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Experience Your Best Florida Keys Vacation

Cross the Overseas Highway to the distant Florida Keys and the symbolism is hard to miss: you're not leaving the country, but then again, you are. From top to bottom, the Keys offer something magically removed and unlike any other US beach vacation.

With everything from sunken treasures in Key Largo and family-friendly exploration in Marathon to trophy fishing in Islamorado and pub-studded Key West, this is a place of must-see and must-do.

Ready to design your own Florida Keys vacation? Start with this Orbitz insider guide for our favorite things to do, best times to go and insider gems.

Best time to take a trip to Florida Keys

Spring break, pleasant weather, festivals or cheap rates -- your Florida Keys vacation is as easy as good timing.

For a perfectly balmy winter or spring break vacation, visit the Keys from December to May for temperatures in the low 80s. It's popular time to visit but the swelling, energetic scene is exactly the draw, especially for those heading to wild Key West.

Visit June through October for the lowest rates and fewer crowds when humidity and regular rainfall are the norm. Celebrate Key West's annual Hemingway Festival in July with readings, a fishing tournament and a look-a-like contest.

Insider tips for Florida Keys travel

Scooner Wharf Bar (Key West)

Hang with boaters and locals, catch live acts from magicians to musicians and feast on fresh seafood.

Mrs. Mac's Kitchen (Key Largo)

Belly up to this quirky roadside diner for delish homemade grub. Swing by for champagne breakfast, or join the lunch/dinner crowd for hogfish and the famed Key Lime Freeze.

Jetpack water sports

Strap on a jet pack and unleash your inner James Bond. Tethered to an unmanned water craft, this thrilling new water sport sets you into flight to turn, hover and cruise 30 feet over the water.

Full Moon Party at Pierre's Restaurant (Islamorada)

Every time there's a full moon, this seaside restaurant throws a huge beach party, complete with fireworks, tiki bars, a Reggae band, stilt walkers, fireblowers, acrobats, face painters and more.

Beach at Fort Zachary Taylor Historic State Park (Key West)

Follow locals to this pristine beach with Australian pines and vibrant reefs.

Things to do in Florida Keys

Ghost Hunters

From Key West's haunted Old Town to Pigeon Key's ghost town, nightly tours beckon ghost hunters of all ages.

Duvall Street (Key West)

Walk this notorious Key West Strip for Sloppy Joes, Lazy Gecko, Cowboy Bills and more.

Ernest Hemingway (Key West)

Explore the former home-turned-museum or celebrate the Pulitzer Prize-winning author in July at the annual Hemingway Days festival.

Fantasy Fest (Key West)

Think Mardi Gras and book your hotel in advance for this 10-day, adult Halloween festival, the biggest of the year.


Charter a private fishing boat in Marathon or Islamorada and catch tarpon, marlin, grouper, mahi -mahi and more.

Harry S. Truman Little White House (Key West)

Take a fascinating tour of the 37th U.S. president's winter home.

John Pennkamp Coral Reef State Park (Key Largo)

Snorkel or scuba dive across a vast and historic underwater park.

Key West Butterfly and Nature Conservatory (Key West)

See the butterflies then buy gorgeous art made from their preserved remains.

Mel Fisher Maritime Museum (Key West)

Discover pirate treasure from New World sunken ships, then buy replica coins and artifacts.

Turtle Hospital (Marathon)

Get an interactive tour and learn about rehabbing and returning sea turtles to their native habitat.

Top Florida Keys vacation package deals

Key West Marriott Beachside Hotel
Casa Marina Key West, Curio Collection by Hilton
Paradise Inn Key West - Adults Only
Custom House by Brightwild
Prices and availability subject to change. Additional terms may apply.

Top rated hotels for your Florida Keys vacation package

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