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

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508 South Street Map
4.5 / 5 115 reviews
  • Stay and Save!
  • Stay and Save!
Hotel only
$165

The newly expanded, updated Southernmost Beach Resort 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 time. Guests can catch some rays on the private beach or visit the... More

Hotel only
$165
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830 Truman Ave Map
4.1 / 5 77 reviews
  • Last Minute Promotion - Save 20% Off
  • Last Minute Promotion - Save 20% Off
Hotel only
$121

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
$121
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902 Whitehead Street Map
3.9 / 5 114 reviews
Hotel only
$159

The historic Lighthouse Court Hotel sits at the heart of downtown Key West, next door to the Key West Lighthouse Museum and across the street from the Ernest Hemingway Home and Museum.  Located just one block from Duval Street, the Lighthouse Court Hotel is within... More

Hotel only
$159
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601 Front Street Map
4.4 / 5 110 reviews
  • Receive every 4th consecutive night free
  • Receive every 4th consecutive night free
Hotel only
$224

The Hyatt Key West Resort and Spa underwent a $10-million-dollar renovation, which included updates to all 118 guestrooms. The resort reflects old-world flair combined with modern amenities, along with impeccable service and a premier location on Front Street near Mallory... More

Hotel only
$224
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1030 Eaton Street Map
3.7 / 5 136 reviews
Hotel only
$149

The Albury Court Hotel sits in a residential neighborhood at the corner of Eaton and Frances Streets in Old Town Key West. Located near the harbor, guests of the Albury Court Hotel can walk to many Key West attractions, including Duval Street, Mallory Square,... More

Hotel only
$149
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725 Truman Avenue Map
4.0 / 5 160 reviews
Hotel only
$159

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
$159
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811 Simonton Street Map
4.1 / 5 117 reviews
Hotel only
$149

A 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 within easy walking distance of many Key West attractions, including the... More

Hotel only
$149
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709 Truman Ave Map
3.8 / 5 128 reviews
Hotel only
$159

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
$159
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200 William Street Map
4.7 / 5 15 reviews
Hotel only
$268

The Marker Resort Key West Luxury starts here. Poised on the pristine waterfront of Key West's historic seaport, The Marker is more than a gleaming new addition to the Florida islands. As the only newly built hotel to grace Old Town Key West in over 20 years, it marks a... More

Hotel only
$268
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430 Duval Street Map
4.0 / 5 146 reviews
  • Save up to 25% off
  • Save up to 25% off
Hotel only
$192

Crowne 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 modern amenities like free high-speed Internet access, and the... More

Hotel only
$192
  • Promo Code Terms and Conditions

    150VACA
    Book a qualifying 4-night flight + hotel vacation package between August 13, 2015 12:00AM CT and September 30, 2015 11:59PM CT, for $1750 or more for travel between August 13, 2015 and December 31, 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.

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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