Key West Holidays

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Where to stay in Key West

Find the best Key West areas and neighborhoods for the activities you enjoy most. Learn more about Key West

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.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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.

Key West Beach Holiday

Unwind on the shore while you watch the sunlight glistening across the water during your Key West holiday. If you're hoping for an unforgettable beach experience, a trip to Key West will definitely deliver. There's a good chance you've heard of Smathers Beach (3 kilometres away). We suggest staying in accommodation close by. However, many sightseers also opt for Key West packages that are closer to South Beach or Boca Chica Nude Beach, two other excellent nearby options.

Things You Should Know About Key West

  • Escape the daily grind at one of our Key West beach hotels. The sweet sound of lapping water and seagulls cawing far above are just a couple of clicks away.
  • If you're searching for lots of room to spread out and relax, Key West private holiday homes are a great choice. After a much-needed family getaway or a few nights escape with that special someone? Grand Maloney Hotel and The Capitana Key West will fit the bill.
  • With a population of approximately 25,800 inches Key West, you're sure to find some friendly locals who are happy to share their sightseeing tips. For more handy hints, check out our Key West things to do page.

Top hotels in Key West

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
The price is S$772 per night from 27 Jan to 28 Jan
S$772
27 Jan - 28 Jan
includes taxes & fees
8.6/10 Excellent! (3,007 reviews)
The right location at the right price. They sent texts to update you on activities on-site.

Reviewed on 19 Jan, 2026

Southernmost Beach Resort and Guesthouses
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
The price is S$660 per night from 1 Feb to 2 Feb
S$660
1 Feb - 2 Feb
includes taxes & fees
8.8/10 Excellent! (1,785 reviews)
The room was very clean and nicely located. The staff was very friendly and accomodating.

Reviewed on 21 Jan, 2026

Oceans Edge Key West Resort, Hotel & Marina
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is S$426 per night from 27 Jan to 28 Jan
S$426
27 Jan - 28 Jan
includes taxes & fees
8/10 Very Good! (2,062 reviews)
It seemed clean. Hotel is dated and bathrooms could use some updating.

Reviewed on 24 Jan, 2026

Ibis Bay Beach Resort
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.

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What to do in Key West

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