Key West Vacations

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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.

  • 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 $680

1 Sunset Key Guest Cottages, A Westin Resort

5 stars
Not yet reviewed

245 Front Street Map

Save 10% on your stay

Experience the incomparable serenity and captivating beauty of a secluded 27-acre island, just ten minutes off Key West, Florida. Soft breezes rustle lush palm trees, azure waters beckon, and all you need or desire is close at hand. Savor fresh island cuisine under the... More

Hotel only $369

2 Ocean Key Resort and Spa A Noble House Resort

4 stars
4.5 / 5 169 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 $364

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 $345

4 Marquesa Hotel

3 stars
4.7 / 5 13 reviews

600 Fleming Street Map

Welcome to Key Wests finest small hotel set in the center of the historic district. A compound of four buildings set around a lush interior garden and two swimming pools the Marquesa offers a quiet retreat for those wanting luxury and privacy. The transformation from 1884... More

Hotel only $432

5 The Westin Key West Resort & Marina

4 stars
4.1 / 5 71 reviews

245 Front Street Map

Save 25% on your stay

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

Hotel only $369

6 Hyatt Sunset Harbor Resort

4 stars
3.9 / 5 34 reviews

200 Sunset Ln Map

Hyatt Sunset Harbor Resort is conveniently located in the heart of Old Town Key West and a short walk to excursions, shopping, dining and all the entertainment Key West has to offer. If walking is not for you a scooter will get you anywhere you want to be. This 40-unit... More

Hotel only $355

7 The Marker Waterfront Resort

4 stars
4.6 / 5 7 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 $326

8 Crowne Plaza KEY WEST-LA CONCHA

3 stars
4.0 / 5 150 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 $429

9 Hyatt Key West Resort and Spa

5 stars
4.4 / 5 110 reviews

601 Front St Map

Receive every 5th consecutive night free

Downtown luxury hotel with spa, water sports and event spaceThe 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... More

Hotel only $355

10 The Gardens Hotel

5 stars
4.8 / 5 13 reviews

526 Angela Street Map

The Gardens Hotel includes a total of 17 richly appointed guest rooms all set within the Historic estate of The Peggy Mills Botanical Key West Gardens. Accommodations at our Bed and Breakfast Key West offer views of the tropical Key West gardens and have expansive outdoor... More

  • 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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