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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.

    Mallory Square

    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

    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.

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Key West Vacation Packages

Hotel only $261

1 The Marker Waterfront Resort

4 stars
4.0 / 5 2 reviews

200 William Street Map

The Marker Resort Key West opened December 2014 as a premier independent 96 room luxury hotel in Old Town Key West. This tropical getaway is centrally located by the historic seaport and is a relaxing refuge set mere steps from the finest Key West has to offer. The... More

Hotel only $249

2 Merlin Guesthouse

3 stars
4.0 / 5 110 reviews

811 Simonton Street Map

Classic Key West guesthouse offers quiet escape at heart of Old TownA classic Key West hotel, the Merlin Guesthouse offers casual lodging on a private, walled compound just one block from famous Duval Street. Centrally located in the Historic District, the hotel sits... More

Hotel only $298

3 Santa Maria Suites Resort

4 stars
4.6 / 5 36 reviews

1401 Simonton Street Map

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

Hotel only $239

4 Southernmost Hotel

5 stars
4.3 / 5 186 reviews

1319 Duval Street Map

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

Hotel only $349

5 Ocean Key Resort and Spa A Noble House Resort

4 stars
4.5 / 5 168 reviews

Zero Duval Street Map

Experience Key West style with an ocean front pool and treatment spaLocated on Duval Street close to Mallory Square, Old Town and Key West Harbor, the Ocean Key Resort & Spa, A Noble House Resort is the ideal place to soak up the Key West style and breathtaking... More

Hotel only $249

6 Crowne Plaza KEY WEST-LA CONCHA

3 stars
4.0 / 5 149 reviews

430 Duval Street Map

Landmark downtown hotel with excellent views of Old Town Key WestCrowne Plaza Hotel Key West - La Concha sits at an enviable Old-Town location, on Duval Street at the heart of the island's eclectic dining, shopping and nightlife. This landmark hotel, built in 1926, offers... More

Hotel only $279

7 Casa Marina Resort - Waldorf Astoria Collection

5 stars
4.2 / 5 218 reviews

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

Hotel only $249

8 Silver Palms Inn

3 stars
4.1 / 5 68 reviews

830 Truman Avenue Map

Save $20 USD per night

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

Hotel only $319

9 Pier House Resort and Caribbean Spa

5 stars
4.4 / 5 121 reviews

1 Duval St. Map

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

Hotel only $259

10 Key Lime Inn

3 stars
3.9 / 5 163 reviews

725 Truman Avenue Map

Historic Key West hotel offers elegant rooms two blocks from Duval St. As a historic Key West hotel, the Key Lime Inn holds a place on the National Historic Register. Constructed in 1854, the hotel underwent an award-winning restoration in 1999, and today, the Key Lime... More

Key West highlights

  • Vandenberg Wreck

    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.

    Waterfront Playhouse

    You can take in a show at the not-for-profit Waterfront Playhouse in Old Town, Key West.

    Sunrise Kiteboarding

    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.