Key West Vacations from $434

Key West Luxury Vacation Packages

We all deserve to spoil ourselves from time to time, so why not splurge on your vacation in Key West? Book one of our Key West Luxury Vacation Packages and experience stays that come with the best of everything, from poolside bars and first-rate spas to a smorgasbord of restaurants and round-the-clock concierge services. Aside from being perfectly pampering, luxury vacations in Key West should also be stress-free and relaxing.

If it’s peace and seclusion you’re seeking, escape to Casa Marina Key West, Curio Collection by Hilton. A private beach, a signature “toes in the sand” dining experience and yoga sessions are just the start of the offerings at this 5-star resort. Add the Hyatt Centric Key West Resort & Spa to your Key West vacation package and take your escape to another level. An award-winning spa, a private boat dock and a year-round outdoor pool are part of the experience at this upmarket getaway.

Romantic Vacation Packages in Key West

If you’re dreaming of waking up to ocean views, taking long walks along the beach and enjoying candlelit dinners with your honey, check out our Key West Romantic Vacation Packages. A popular destination for honeymooners, Key West is home to idyllic stays that cater to lovebirds, like Pier House Resort & Spa. It has everything newlyweds need: a full-service spa, hot tubs and a private white-sand beach, as well as an excellent location close to lively Mallory Square. Or, stroll hand-in-hand along garden paths and relax under poolside cabanas at Southernmost Beach Resort during your vacation in Key West.

When you can tear yourself away from your cozy surroundings, get out and do the things you love with the one you love. Make new memories with a Key West Photo Shoot at Your Resort or the Beach. Or take the first step toward your new life together and book a Key West Marriage Proposal Package. Browse our Things to Do in Key West guide and add some romantic tours and experiences to your Key West vacation package.

Where to Stay in Key West

Key West is a sun-soaked island-city perched at the western edge of the Florida Keys. Here’s our roundup of the best neighborhoods to stay for your vacation in Key West:

• Key West Historic District: In this busy area you’ll find historical landmarks, superb museums and pretty gardens alongside great shopping, dining and nightlife.
• Duval Street: Packed with retail outlets, bars, restaurants, live music venues and street performers, the fun never ends on this lively street.
• Historic Seaport: Key West’s bustling marina is the place to be for tasty eats, art and water sports excursions.
• Bahama Village: Into architecture and food? Stay in this neighborhood to enjoy its colorful houses and dine at open-air restaurants.
• New Town: If you want to be away from the tourist crowds yet a short hop from major sights, laid-back New Town is the perfect place to spend your vacation in Key West.

Top Things to Do

Whether you want to be active or take things slow, visit a museum or feast until your heart’s content, vacations to Key West offer something for all types of travelers:

• Historical: Get a local history and culture fix at Ernest Hemingway Home and Museum and Harry S. Truman Little White House. Don’t miss Dry Tortugas National Park either.
• Beach: Sun, sea, sand and water sports are the order of the day at popular spots like Smathers Beach, South Beach and Higgs Beach.
• Entertainment: Head to Mallory Square for street performers, food carts and spectacular sunsets. If you’re in the mood to party, join a Key West pub crawl or a craft cocktail crawl.
• Family-Friendly: Traveling with the kids? There’s fun for all ages at the Key West Shipwreck Museum and Key West Aquarium.
• Sports: It’s time to get adventurous! Add a Snorkel Adventure of Coral Reef to your Key West vacation package or try parasailing. Alternatively, join a Key West Mangrove Kayak Eco Tour.

How to Find Cheap Package Deals

Landing the best deals on vacations to Key West is a breeze. Just key in your preferred travel dates and filter your property search by things like amenities, price and star ratings. A top tip for scoring a cheap hotel in Key West is to arrive in June, July and August. Generally, hotels are less expensive and have more availability around this time. December, January and February are the busiest months in Key West.