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

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is S$329 per night from 28 Apr to 29 Apr
S$329
28 Apr - 29 Apr
includes taxes & fees
8.4/10 Very Good! (2,144 reviews)
Room was clean and nice. Be prepared for the wildlife surround the pool. (Chickens and Iguanas). One thing that I found out was that I caught one of the members of the cleaning staff peering into my room when I had the window cracked.

Reviewed on 26 Apr, 2026

Blue Flamingo Resort Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is S$367 per night from 11 May to 12 May
S$367
11 May - 12 May
includes taxes & fees
8.6/10 Excellent! (2,178 reviews)
Check in process was a disaster! We arrived a little over an hour early and were assured housekeeping would get right on our room! Not the case, and we ended up requesting at check in time to let us into our room! The room we were in definitely needs some upgrading.The shuttle service they offer ...

Reviewed on 25 Apr, 2026

Beachside Resort & Residences
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is S$389 per night from 26 May to 27 May
S$389
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (1,807 reviews)
The resort exceeded all of my expectations. We had an ocean view suite with gorgeous sunrise views, a comfortable bed, relaxing balcony and huge clean bathroom. All of the staff were kind and helpful. The property was very well maintained. There are a lot of families with small kids, so be prepared ...

Reviewed on 25 Apr, 2026

Margaritaville Beach House Key West
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.

Popular places to visit

What to do in Key West

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