Key West Vacations

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Experience Your Best Key West Vacation

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.

  • 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.

  • 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.

Key West Vacation Packages

Hotel only $199

1 Southernmost Hotel

5 stars
4.3 / 5 198 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 $268

2 Santa Maria Suites Resort

4 stars
4.7 / 5 38 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

3 Pier House Resort and Spa

5 stars
4.4 / 5 128 reviews

1 Duval St. Map

Waterfront luxury just steps from Duval Street and Mallory SquareLocated at the northern end of Duval Street, Pier House Resort and Spa treats guests to Gulf of Mexico views and a location in the island's lively tourist district near Mallory Square. A waterfront... More

Hotel only $153

4 Parrot Key Hotel and Resort

3 stars
4.0 / 5 164 reviews

2801 North Roosevelt Blvd Map

Newly opened waterfront hotel offers rooms, suites and villasNewly opened in 2008, the Parrot Key Hotel and Resort sits on five acres of lushly landscaped property overlooking the Gulf of Mexico. Located bayside on U.S. 1, the Parrot Key Hotel and Resort offers... More

Hotel only $179

5 Chelsea House

3 stars
3.8 / 5 145 reviews

709 Truman Ave Map

Historic Key West hotel offers elegant rooms at the heart of Old TownThe historic Chelsea House Pool and Gardens sits at the heart of Old Town Key West. Offering rooms in grand Victorian mansions, which date from 1888 and 1906, Chelsea House Pool and Gardens has classic... More

Hotel only $163

6 Silver Palms Inn

3 stars
4.1 / 5 75 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 $209

7 Casa Marina Resort - Waldorf Astoria Collection

5 stars
4.2 / 5 238 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 $241

8 Ocean Key Resort and Spa A Noble House Resort

4 stars
4.5 / 5 185 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 $339

9 Hyatt Windward Pointe

4 stars
4.4 / 5 37 reviews

3675 South Roosevelt Blvd Map

Enjoy homey and secluded condominiums on the south side of Key WestOn the southeast side of Key West, the Hyatt Windward Pointe offers a secluded getaway with residential-style accommodations near the Key West airport and southern beaches like Smathers Beach. From the... More

Hotel only $209

10 Sheraton Suites Key West

4 stars
4.2 / 5 132 reviews

2001 South Roosevelt Boulevard Map

Save 20% on your stay

Key West beach-front hotel offers updated suites, modern amenities Sheraton Suites Key West sits across the street from Smathers Beach on the south coast of Key West. The airport adjacent hotel offers suites decorated in Caribbean colors, and the property has undergone a... More

  • Promo Code Terms and Conditions

    150VACA
    Book a qualifying 4-night flight + hotel vacation package between January 1, 2014 12:00AM CST and June 30, 2015 11:59PM CST, for $1000 or more for travel between January 1, 2014 and September 30, 2015 via Orbitz and instantly receive $150 off the hotel portion of your booking through the use of the promotion code. Limit one discount per hotel room and one promotion code per booking. Discounts are not redeemable for cash for any reason. Promotion codes cannot be resold. Any attempt at fraud will be prosecuted to the fullest extent of the law. Void where prohibited, taxed or restricted. Orbitz reserves the right to change or limit the promotion in its sole discretion. Promo code not valid for Las Vegas, NV bookings.

  • 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.

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