Key West Vacations
Your Trip to Key West
The Florida Keys is a group of islands off the southern tip of Florida. The largest among them is Key West, which also happens to serve as one of the largest tourist destinations in the Keys. Key West has a reputation for laid-back island living with an active nightlife. This reputation draws the attention of visitors looking for the ultimate in relaxation with an occasional bit of excitement thrown in.
Key West isn't just about stretching out on Higgs Beach, though. Visitors will find plenty of attractions, whether they want to explore the history of Key West through the Key West Shipwreck Museum or take a tour of the Harry S. Truman Little White House, once known as the Winter White House and used as recently as the Clinton administration.
Best time to take a vacation to Key West
One of the best times to visit Key West is during the off-season when the crowds thin out a bit and the prices drop. The off-season in Key West occurs during the hottest summer months, lasting from June to mid-August. The temperature tends to rise to average highs in the upper 80s, but it's the Florida humidity that visitors may find challenging. Summer thunderstorms are also frequent in the afternoons but are fortunately brief enough as to not ruin an entire day's sightseeing. Most attractions are still going strong during the off-season. June 6 to 10 is Key West Pride Week, featuring the regional symphony, film festival, bike tours and a street fair. July 17 to 22 is a celebration of Ernest Hemingway's time in town with the Key West Hemingway Days.
Insider tips for Key West travel
West Martello Tower
Enjoy multiple views of the island from the garden-covered platform of West Martello Tower.
In Mallory Square, you can watch the sunset over the ocean while enjoying a variety of street performances. It's a tradition among visitors to the island.
Tavern N Town
Have a taste of Caribbean Cuisine with a Florida touch at the Tavern N Town, a bi-level shared restaurant eatery. Tavern is on the bottom and features small plate dishes while Town on the top level serves a more traditional plate for visitors.
Michaels steakhouse is a bit out of the way in a residential neighborhood but worth the effort of finding. The restaurant specializes in great steaks and fresh seafood dishes.
Nine One Five
An intimate romantic atmosphere that's perfect for a date in Key West accompanies the delicious food at Nine One Five. There's no specific cuisine, with the food being an eclectic mix of dishes.
Sign up to receive our best deals
Get insider access to our best hotel deals, coupons and more!
Key West Vacation Packages
Quiet, beachfront hotel offers abundant amenities on Key WestThe Southernmost Hotel sits at the south end of Duval Street near Key West's famous Southernmost Point of the United States. And while Southernmost Hotel is slightly removed from the hustle of the main tourist... More
Adults-only hotel with private balconies, pool bar, beach near Old Town Ideal for singles groups or couples looking for a romantic getaway, the adults-only Banana Bay Resort and Marina sits on the waterfront along the Gulf of Mexico, just east of the Old Town area... More
Lavishly equipped suites in a tropical garden setting near Old Town The Santa Maria Suites Resort sits just steps from the beach near the southern end of Duval Street. Located on the quiet, south side of the island, the Santa Maria Suites Resort offers a secluded... More
Waterfront luxury just steps from Duval Street and Mallory SquareLocated at the northern end of Duval Street, the Pier House Resort and Caribbean Spa treats guests to Gulf of Mexico views and a location in the island's lively tourist district near Mallory Square. A... More
Newly expanded hotel with beach and oceanfront guestroomsThe newly expanded, updated Southernmost on the Beach hotel stretches along a secluded section of Key West coastline, far enough to provide respite from downtown craziness, but close enough to hit the scene any... More
1500 Reynolds Street Map
Best of Waldorf - Includes hotel credit
Historic beachfront luxury resort on the south side of Key WestBuilt in 1920, the Casa Marina Resort holds a spot on the National Register of Historic Places. The iconic hotel offers an ideal mix of laid-back elegance, old-Key West ambiance and modern luxury. Nestled on... More
Affordable elegance for a luxury vacation or weekend getawayThe Silver Palms Inn Key West is located in Historic Old Town. This Florida hotel offers guests a contemporary appearance, with aquamarine accents set against a background of earth-tone accents. Regardless if... More
1435 Simonton Street Map
Best of Waldorf - Includes hotel credit
Luxury resort, on-site water sports along Key West's only natural beachThe Reach Resort underwent a major renovation and now features sumptuous accommodations and abundant amenities on the island's only natural beach. Located at the end of Simonton Street just east of the... More
Island luxury overlooking Sunset Pier, few steps from Duval StreetThe Westin Key West Resort & Marina sits at the heart of Old Town Key West near the famous Sunset Pier at Mallory Square, and just a block from Duval Street. Guests of the Westin Key West Resort &... More
Azul Key West is a classic Victorian mansion, just three blocks from Duval Street and Hemingways House. Located in the center of Key Wests Historic District, this former cigar barons mansion boasts tri level, downpour blue decks which surround the carriage house,... More
*Savings based on Flight + Hotel vacation package bookings of 5 or more nights with individual calculable components on www.orbitz.com from January 1, 2014 through June 30, 2014, as compared to 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.
Key West highlights
Try a guided dive at the Vandenberg Wreck for a beginner's level trip around a newly sunk ship.
Yoga on the Beach
Relax with an early morning yoga session on the beach at the Southernmost hotel. The session is suitable for beginners and experienced students alike.
You can take in a show at the not-for-profit Waterfront Playhouse in Old Town, Key West.
Learn to kiteboard on a windy day with certified instructors at the Sunrise Kiteboarding school.
Key West Aquarium
You'll be able to get a close-up look at the undersea residents of the island's surrounding waters at the Key West Aquarium.
Western Dry Rocks
The dry rocks are a multilevel reef that can be explored by diving. Snorkeling is an alternative for those without diving experience.
South Florida Symphony Orchestra
Head over to the Tennessee Williams Theatre to catch a performance from the professional musicians of the South Florida Symphony Orchestra.
Key West Golf Club
Take in a round or two of golf at the Key West Golf Club. Rental clubs are available for your use.
The Studios of Key West
The Studios is a nonprofit center offering art exhibitions and concerts throughout the year, often showcasing local talents.
Ernest Hemingway Home and Museum
Located in the house that the Nobel Prize-winning Hemmingway spent 10 years writing in, this museum contains memorabilia of his life. Guided tours are available through the museum.