Key West Holidays

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Our guide on 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

Key West Holiday

Things to do in and around Key West

Shopping

In Key West, visit The Kite House for unique gifts or We Cycle Key West for cycling gear. If you're up for a drive, check out Big Pine Key Flea Market, located 46.7km away, offering a vibrant atmosphere and a mix of local goods.

Recreation

The MLK Community Pool & Community Center offers a refreshing outdoor swimming experience, perfect for families seeking a fun day out. For golf enthusiasts, the Key West Golf Club provides a scenic course surrounded by lush landscapes, while the Red Barn Theater showcases captivating performances, blending culture and entertainment in a romantic setting.

Adventure

In Key West, embark on a thrilling snorkelling adventure at the vibrant coral reefs, teeming with marine life. Experience the exhilaration of parasailing high above the azure waters, or take a sunset kayak tour through serene mangroves, soaking in the breathtaking views of the sun dipping below the horizon.

Nightlife

Key West's nightlife pulses with energy, from the lively bars on Duval Street to the iconic sunset celebrations at Mallory Square. Enjoy a cocktail at Sloppy Joe's or dance the night away at The Green Parrot. The atmosphere is vibrant, with music and laughter filling the air.

*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, Florida, is an ideal destination for families and business travellers alike, offering a blend of culture, stunning beaches, and outdoor experiences. Popular attractions include historic houses and national parks, making it a great spot for those seeking both relaxation and adventure. Explore top local points of interest and enjoy the vibrant atmosphere that Key West vacations have to offer, ensuring a memorable trip for all visitors.

  • Duval Street: Experience the vibrant heart of Key West on Duval Street, where lively bars, boutique shops, and local eateries create an energetic atmosphere. This iconic thoroughfare is perfect for strolling, people-watching, and immersing yourself in the unique city vibes that define Key West.
  • Mallory Square: Known for its stunning sunsets, Mallory Square is a bustling gathering place filled with street performers, artists, and food vendors. Join the sunset celebration, where the lively city vibes combine with breathtaking views, making it a memorable experience for all visitors.
  • Southernmost Point: Marking the southernmost point in the continental USA, this iconic landmark offers a glimpse into Key West's rich culture. Capture a photo at this symbolic spot, surrounded by the vibrant atmosphere that encapsulates the spirit of the island.

Best time to go to Key West

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Tips to save on your trip to Key West

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Key West during the low season (August to October) for more affordable options.
  • 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 65 532 cm 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.

Our pick of the best Key West Hotel Deals

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 NZ$385 per night from 25 May to 26 May
NZ$385
25 May - 26 May
includes taxes & fees
8.4/10 Very Good! (2,181 reviews)
OUTSTANDING!! I had stayed here for 3weeks back in February on a work trip and they were Fantastic!! So, I notified management that I was coming back for my 33rd Wedding Anniversity and when we arrived there were Red Roses, Balloons and Champagne and the same room that i was in prior was waiting ...

Reviewed on 4 May 2026

Blue Flamingo Resort Key West
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 NZ$540 per night from 18 May to 19 May
NZ$540
18 May - 19 May
includes taxes & fees
8.8/10 Excellent! (1,803 reviews)
Breakfast was great. Check in was easy. Pool was refreshing.

Reviewed on 3 May 2026

Margaritaville Beach House Key West
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
The price is NZ$753 per night from 25 May to 26 May
NZ$753
25 May - 26 May
includes taxes & fees
8.4/10 Very Good! (635 reviews)
The Best Hotel in Key West 10 stars!!!!

Reviewed on 29 Apr 2026

Casa Marina Key West, Curio Collection by Hilton
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.