Key West Vacations

Hotel options

Hotel stay must be within date range of Leave and Return.

Room 1
*Ages of children at time of trip (for pricing, discounts)

Key West Flight + Hotel packages

  

Earn up to 5% on hotels and 1% on flights - It's free!

By clicking, I agree to the terms and conditions.

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 Hotels

From $231

1 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

From $164

2 Southernmost Hotel

4 stars
4.3 / 5 200 reviews

1319 Duval Street Map

The 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 strip, it is still close enough for guests to join the... More

From $149

3 Merlin Guesthouse

3 stars
4.0 / 5 118 reviews

811 Simonton Street Map

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

From $159

4 Chelsea House

3 stars
3.8 / 5 145 reviews

709 Truman Ave Map

The 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 accommodations with modern amenities. The hotel is located just two... More

From $199

5 Parrot Key Hotel and Resort

3 stars
4.0 / 5 167 reviews

2801 North Roosevelt Blvd Map

Guests at the Parrot Key Hotel and Resort in Key West can grab breakfast, lunch, an afternoon snack or their favorite tropical drink poolside at Cafe Blue. The hotel is conveniently located off Overseas Highway US Route 1 to provide instant access to several dining... More

From $149

6 Albury Court Hotel

3 stars
3.6 / 5 174 reviews

1030 Eaton Street Map

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

From $169

7 Courtyard by Marriott Key West Waterfront

3 stars
4.2 / 5 39 reviews

3031-41 North Roosevelt Boulevard Map

Rate includes breakfast

Get FREE high-speed Internet access at the Courtyard Key West Waterfront. This Key West hotel is located on the Gulf of Mexico in the "New Town" section of Key West. The Courtyard Key West is located within a 10 minute drive of any attraction on the island and features... More

From $166

8 The Gates Hotel Key West

4 stars
2.9 / 5 49 reviews

3824 N. Roosevelt Blvd. Map

Save 25%

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

From $171

9 Silver Palms Inn

4 stars
4.1 / 5 77 reviews

830 Truman Ave Map

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

From $178

10 Crowne Plaza KEY WEST-LA CONCHA

3 stars
4.1 / 5 167 reviews

430 Duval Street Map

Save up to 25% off

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

  • Promo Code Terms and Conditions

    125TRIP
    Book a qualifying 4-night flight + hotel vacation package between June 1, 2015 12:00AM CST and September 30, 2015 11:59PM CST, for $1000 or more for travel between June 1, 2015 and December 31, 2015 via Orbitz and instantly receive $125 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.

Sign up to receive our best deals

Get insider access to our best hotel deals, coupons and more!