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.

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.

Key West Vacation Packages

Free Cancellation
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3800 N Roosevelt Blvd Map
5.0 / 5 1 reviews
  • Grand Opening Promotion - Save 25%!
  • Grand Opening Promotion - Save 25%!
Hotel only
$284

Hotel 24 North Key West is a brandy new, lifestyle hotel offer pool and ocean views, a full pool-side bar serving breakfast and dinner, full fitness center and well-sized, tastefully appointment guest rooms with gorgeous views. More

Hotel only
$284
Free Cancellation
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3824 N. Roosevelt Blvd. Map
3.1 / 5 48 reviews
  • Stay tonight save 42%
  • Stay tonight save 42%
Hotel only
$233

The Gates is a new boutique hotel in Key West offering an intimate setting that invites guests to celebrate the island's colorful history and creative spirit. Mixing contemporary design with retro Floridian flair, The Gates Hotel features 100 guestrooms with modern... More

Hotel only
$233
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508 South Street Map
4.6 / 5 132 reviews
  • Stay Longer and Save More!
  • Stay Longer and Save More!
Hotel only
$291

A member of the exclusive Southernmost hotel collection, Southernmost on the Beach, in Key West, is a small luxury inn with a big personality. While it s low-level, colonial-inspired design is a testament to the island s rich history, the hotel s 124 fully renovated guest... More

Hotel only
$291
Free Cancellation
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830 Truman Ave Map
4.2 / 5 90 reviews
Hotel only
$324

Key West Newest Luxury Boutique Hotel. Enjoy affordable elegance at the new Silver Palms Inn,located downtown Key West, in Historic Old Town offering 50 Deluxe contemporary guest rooms surrounding a courtyard,deck,and beautiful pool. Among the amenities are 40-inch LCD... More

Hotel only
$324
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Zero Duval Street Map
4.5 / 5 160 reviews
Hotel only
$426

Located in Key West's northwestern section, the Ocean Key Resort Key West features a well-equipped fitness center, a popular bar, a large banquet room, numerous pools, a sizable pier, a tennis court and a business center with several computers. Guests can visit the... More

Hotel only
$426
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1401 Simonton Street Map
4.7 / 5 43 reviews
Hotel only
$558

With a facade that's inspired by Art Deco architecture, the Santa Maria Suites Resort in Key West is a tropical retreat that offers seafront lodging. Featuring full kitchens, the 35 suites in this boutique property are inspired by apartment living. Forty-eight-inch HDTVs... More

Hotel only
$558
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811 Simonton Street Map
4.1 / 5 128 reviews
Hotel only
$192

The historic Merlin Guesthouse in Key West offers a tranquil escape just steps from all the action. You can languish in gorgeously refurbished guestrooms and cottages nestled around a private flowered courtyard, and you'll love to start each day with a continental... More

Hotel only
$192
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725 Truman Avenue Map
4.0 / 5 164 reviews
Hotel only
$279

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 Inn offers classic accommodations with modern amenities at the center of... More

Hotel only
$279
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430 Duval Street Map
4.0 / 5 157 reviews
  • Save up to 25% off
  • Save up to 25% off
Hotel only
$336

Built in 1926, the Crowne Plaza Key West La Concha in Key West is a boutique hotel that combines elements of Art Deco styling with Mediterranean architecture. Striped awnings and red roof tiles dominate the facade. In harmony with the property's early years, the interior... More

Hotel only
$336
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709 Truman Ave Map
3.8 / 5 136 reviews
Hotel only
$279

The historic Chelsea House 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 accommodations with modern amenities. The hotel is located just two blocks from famous... More

Hotel only
$279

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.

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    50VACA
    Book a qualifying 4-night flight + hotel vacation package between January 1, 2014 12:00AM CT and March 31, 2016 11:59PM CT, for $1000 or more for travel between January 1, 2014 and June 30, 2016, via Orbitz and instantly receive $50 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.