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
A white building with shutters, palm trees, and a lawn.

Old Town Key West

4 out of top 10 points of interest in this area

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Florida Keys Beaches.

Find hotels in Old Town 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

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 NZ$386 per night from 17 Aug to 18 Aug
NZ$386
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (2,397 reviews)
"The property was very nice but in need a daily maintenance: Lawn cleaned and mowed to keep up resort type appearance that it should. Probably should hose off the stairs and benches of chicken droppings, also to look resort worthy. All said and done, the room was exceptionally nice (ice maker didn't ..."

Reviewed on 1 Aug 2026

Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is NZ$388 per night from 1 Sept to 2 Sept
NZ$388
1 Sept - 2 Sept
includes taxes & fees
Southernmost Beach Resort and Guesthouses
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$327 per night from 1 Sept to 2 Sept
NZ$327
1 Sept - 2 Sept
includes taxes & fees
Blue Flamingo Resort Key West
See all 2,637 properties in 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.

Stay near popular Key West attractions

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.
See properties

What to do in Key West

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

NZ$79
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
12 hours Day at Key West With Boat Tour and Snorkeling

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

NZ$48
per adult
90% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

NZ$98
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
See all activities 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.

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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.