Beginning of main content

5178 Travelers rated Florida Keys highly for Sunsets and Running

Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.
Book a package and join the 188 others who’ve received 100% off their flights this year!
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Book a package and join the 188 others who’ve received 100% off their flights this year!

Top Florida Keys vacation deals

4-night vacation deals

5-night vacation deals

6-7 night vacation deals

4-star vacation deals

3-star vacation deals

2-star vacation deals


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.

Things to do in Florida Keys

Turtle Hospital (Marathon)

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

John Pennkamp Coral Reef State Park (Key Largo)

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

Harry S. Truman Little White House (Key West)

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

Mel Fisher Maritime Museum (Key West)

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

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.

Key West Butterfly and Nature Conservatory (Key West)

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

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.

Fishing

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

Insider tips for Florida Keys travel

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.

Scooner Wharf Bar (Key West)

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

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.

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.

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

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

Top Rated Hotels for your Florida Keys Vacation

Tranquility Bay Beachfront Hotel and Resort
Tranquility Bay Beachfront Hotel and Resort
4.0 out of 5.0 2600 Overseas Hwy, Marathon, FL
Free Cancellation
$239
4.3/5 (80 reviews)

This is a little slice of paradise! The little cottages have every amenity and are spotless. Three pools, a beach, and water sports all wrapped up with a beautiful bow.

Reviewed on Mar 12, 2020
Guests of Tranquility Bay Beachfront Hotel and Resort have access to a private beach, 3 outdoor pools, and a fitness center. You can take advantage of free parking ...
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 out of 5.0 97000 Overseas Hwy, Key Largo, FL
$270
4.7/5 (15 reviews)

Beautiful property. Very relaxing vacation for my family. Staff was very friendly and accommodating! The resort was very clean. Room was beautiful! I can't say enough great things about this place.

Reviewed on Sep 24, 2019
Guests of Baker's Cay Resort Key Largo, Curio Collection by Hilton have access to a private beach, 2 outdoor pools, and a fitness center. You can take advantage ...
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph Collection
4.0 out of 5.0 97450 Overseas Highway, Key Largo, FL
Free Cancellation
$219
4.6/5 (27 reviews)

Its a beautiful property to relax and enjoy the water and sunset.

Reviewed on Feb 12, 2020
Built in 2016, the brand new Playa Largo Resort & Spa, Autograph Collection features a full-service spa, an outdoor pool, and a 24-hour fitness center. Free ...

Things To Do during your Florida Keys Vacation

See all 270 things to do in Florida Keys

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.