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Key West Holidays

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Where to stay in Key West

Find the best Key West areas for the activities you enjoy most. Learn more about Key West
Learn more about Key West
A white lighthouse with a small adjacent building, surrounded by lush green trees and a clear blue sky.

Old Town Key West

Old Town Key West captures the essence of island history with its pastel Victorian "Conch Houses" and lively atmosphere. Stroll past Ernest Hemingway's home where six-toed cats roam freely. The charming district buzzes with activity from Duval Street to Mallory Square's famous sunset celebrations. Explore this walkable area to discover hidden treasures like the Truman Little White House and Key West Butterfly Conservatory. Live music spills from open-air bars while local galleries showcase island artists. Rent a bicycle to navigate the narrow streets or simply wander among the bougainvillea-draped fences.

A row of pastel-colored houses with white railings and a clear blue sky.

New Town

Key West's New Town area offers a refreshing glimpse into local island living. Here residential streets create a peaceful retreat from tourist crowds. Find budget-friendly hotels and everyday conveniences like shopping plazas and supermarkets. Smathers Beach is just a short drive away for sun seekers. The area's suburban character makes it perfect for travellers who want authentic experiences with practical amenities. Most locals choose New Town for its relaxed pace and affordable dining options.

A two-story house with green shutters and a wooden balcony.

Key West Historic District

Step into a vibrant slice of history in Key West's Historic District. This charming area blends Victorian architecture with tropical flair along its narrow brick streets. The area boasts Hemingway's former home, the Truman Little White House, and sunset celebrations at Mallory Square. Duval Street forms the lively backbone of this walkable district. Visitors can explore art galleries by day and enjoy live music venues by night. Fort Zachary Taylor offers swimming and Civil War history just steps from the six-toed cats at the Hemingway House.

A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.

Downtown Key West

Historic City centre Key West captivates with its colourful charm and rich maritime legacy. Stroll along iconic Duval Street where Victorian architecture meets lively bars and shops. Ernest Hemingway's former home welcomes visitors with its famous six-toed cats and literary history. Join the nightly Sunset Celebration at Mallory Square where street performers entertain against breathtaking Gulf views. The Historic Seaport offers boat tours and waterfront dining options. Most attractions sit within easy walking distance, making City centre Key West perfect for exploring on foot.

A street with a pharmacy, a theater, and a yellow building.

Uptown - Upper Duval

If you're spending some time in Uptown - Upper Duval, Southernmost Point and Duval Street are top sights worth seeing.

Discover the most popular places to visit in Key West

A street with a pharmacy, a theater, and a yellow building.

Duval Street

9.2/10 (20,928 reviews)
Stroll the vibrant heart of Key West where historic architecture meets lively entertainment. Evening visits offer the full experience of Duval Street's renowned music scene and spirited local culture.

What to do in Key West

12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

S$74
per adult
90% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
See all activities in Key West

Key West Hotel Deals

Outdoor pool, open 8:00 AM to 7:00 PM, pool umbrellas, pool loungers

Tranquility Guest House

Tranquility Guest House
2.0 star property
0.3 km from Key West
9.8 out of 10, Exceptional, (9 reviews)
"Great location, clean, nice small pool. Only negative was no coffee."
The price is S$282
includes taxes & fees
18 Aug - 19 Aug
Tranquility Guest House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Key West

Frequently Asked Questions

How much does a Key West holiday package cost?

Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Key West costs! Our packages make travel planning easier and save you more.

What are the cheapest months to go to Key West?

August, September and October are the best times to search for cheap Key West holiday packages. Choosing to travel in quieter periods means you can usually find reduced prices on hotels and flights.

How many days is enough for Key West?

Key West holidays come in all shapes and sizes, but to really sink your teeth into this place, we'd say 3 days is a good ballpark. This will mean you can visit top sights like Key West Aquarium and Harry S. Truman Little White House along with underrated spots. Don't miss out on neighbourhoods such as Key West Historic District and Old Town Key West either. If you're clever with your time, you may even be able to take a day trip from Key West too.

Is it worth booking a holiday package to Key West?

Key West offers everything you need for an amazing trip. Begin your Key West holiday on a high note by visiting popular attractions like Smathers Beach.

How to find the best Key West package deals?

Bagging a cheap Key West package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, add a couple of filters and browse what's available. You can personalise your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Key West package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.

Is it cheaper to book a Key West holiday as a package?

Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component separately. And you'll still have the freedom to create a personalised Key West holiday by choosing your favourite airline, accommodation type and car class.

When to book a holiday package to Key West?

If you're considering a spur-of-the-moment Key West trip, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your hotels and flights by booking ahead.

How to plan a trip to Key West?

  1. Choose your travel dates: What you'd like to do in Key West and your favourite season will help you decide when to travel.
  2. Calculate your budget: Ensure you have enough money to cover everything from meals and transportation to activities and airfares. Your hotel will probably be the biggest expense during your trip to Key West.
  3. Decide how long to go for: Now that you're more familiar with Key West, you can figure out the right length of your holiday. Pull together a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalised Key West holiday package.

Book with confidence

Things to do in and around Key West

Key West is an ideal destination for family, city, and business-themed vacations, offering a variety of attractions. Visitors can explore vibrant shopping areas, enjoy relaxing resort stays, and partake in fun activities like kayak trips. The island also boasts a lively atmosphere with live music and numerous vacation attractions that showcase its unique charm. Whether you seek adventure or leisure, Key West promises a memorable experience for all.

Shopping

For a delightful shopping experience in Key West, visit The Kite House and We Cycle Key West, both offering unique local items. If you're up for a drive, the Big Pine Key Flea Market, located 46.7km away, features a vibrant atmosphere with various vendors and treasures to discover.

Recreation

Enjoy a refreshing swim at the MLK Community Pool, perfect for families seeking outdoor fun. Relish a round of golf amidst the scenic beauty at Key West Golf Club, or immerse yourself in the vibrant culture and entertainment at the Red Barn Theater, ideal for a romantic evening.

Adventure

Experience the thrill of parasailing above the clear turquoise waters of Key West, offering breathtaking views of the coastline. For the adventurous, snorkelling at the vibrant coral reefs of the Florida Keys National Marine Sanctuary promises an unforgettable underwater adventure filled with marine life.

Embark on a kayaking tour through the mangroves, where you can explore the unique ecosystem while spotting local wildlife, or try paddleboarding at sunset, gliding over calm waters as the sky transforms into a canvas of colours.

For a unique experience, take a thrilling jet ski tour around the island, zooming past picturesque beaches and historic landmarks, or dive into a scuba diving excursion to explore the captivating shipwrecks and coral gardens beneath the waves.

Nightlife

Key West’s nightlife buzzes with energy, featuring vibrant bars like Sloppy Joe's for lively music and cocktails. For a laid-back vibe, visit the Green Parrot, where you can enjoy local bands. Don’t miss sunset celebrations at Mallory Square for a festive atmosphere before heading out.

Find the best attractions in Key West

Key West is an ideal destination for family, city, and business-themed vacations, offering a delightful mix of beach, national parks, and historic houses. Visitors can immerse themselves in the local culture while enjoying outdoor experiences. Don’t miss attractions like the Key West Aquarium and other Florida Keys highlights for a memorable getaway.

  • Mallory Square: Experience the vibrant city vibes at Mallory Square, where locals and tourists gather to enjoy street performances, art displays, and breathtaking sunset views. This lively square is perfect for soaking in the atmosphere of Key West.
  • Southernmost Point: Visit the iconic Southernmost Point, a symbolic landmark that represents the southernmost tip of the continental United States. It’s a must-see for its cultural significance and a fantastic photo opportunity with its colourful buoy.
  • Smathers Beach: Relax at Smathers Beach, the largest beach in Key West, known for its soft sands and crystal-clear waters. This beach is ideal for sunbathing, swimming, and water sports, offering a quintessential beach experience.

Tips to save on your trip to Key West

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Key West.
  • Consider traveling during the off-peak season (typically August to October) for more affordable package holidays to Key West.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.