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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.

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 $159

1 Southernmost Hotel

5 stars
4.3 / 5 176 reviews

1319 Duval Street Map

Stay and Save Up To 10%

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 $199

2 Pier House Resort and Caribbean Spa

5 stars
4.4 / 5 118 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 $154

3 Banana Bay Resort and Marina

2 stars
3.2 / 5 172 reviews

2319 N Roosevelt Blvd Map

Adults-only hotel with private balconies, pool bar, beach near Old Town Ideal for singles groups or couples looking for a romantic getaway, the adults-only Banana Bay Resort and Marina sits on the waterfront along the Gulf of Mexico, just east of the Old Town area... More

Hotel only $218

4 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 $159

5 Silver Palms Inn

3 stars
4.0 / 5 65 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 $199

6 The Reach Resort - Waldorf Astoria Collection

4 stars
4.0 / 5 219 reviews

1435 Simonton Street Map

Best of Waldorf - Includes hotel credit

Luxury resort, on-site water sports along Key West's only natural beachThe Reach Resort underwent a major renovation and now features sumptuous accommodations and abundant amenities on the island's only natural beach. Located at the end of Simonton Street just east of the... More

Hotel only $269

7 Southernmost on the Beach

5 stars
4.5 / 5 120 reviews

508 South Street Map

Stay and Save Up To 10%

Newly expanded hotel with beach and oceanfront guestroomsThe newly expanded, updated Southernmost on the Beach hotel 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... More

Hotel only $169

8 Fairfield Inn & Suites by Marriott Key West

3 stars
3.8 / 5 97 reviews

2400 North Roosevelt Boulevard Map

Updated leisure hotel with rooms, suites minutes from Old Town Key WestLocated just outside Old Town Key West, the Fairfield Inn and Suites Key West overlooks the Gulf of Mexico on the island's north coast. Fairfield Inn and Suites Key West has 106 guestrooms and a... More

Hotel only $249

9 Hyatt Key West Resort and Spa

5 stars
4.3 / 5 108 reviews

601 Front St Map

Receive every 4th 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 $219

10 Ocean Key Resort and Spa A Noble House Resort

4 stars
4.5 / 5 163 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

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.