Key West Holidays

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to NZ$545 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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
Default Image

Key West Historic District

4 out of top 10 points of interest in this area
4.5/5(10 area reviews)

Travellers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to stop by Duval Street and Ernest Hemingway Home and Museum.

Find hotel + flight trips in Key West Historic District

Our pick of the best Key West Hotel Deals

Havana Cabana at Key West
Havana Cabana at Key West
4 out of 5
3420 N. Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is NZ$247 per night from 2 Oct to 3 Oct
NZ$247
per night
2 Oct - 3 Oct
8.6/10 Excellent! (1,588 reviews)
"Beautiful property and great service. Will definitely be coming back to this hotel. Transportation and parking were a great experience with 0 complications. Room was very clean and spacious, loved it all !!"

Reviewed on 23 Sep. 2024

Havana Cabana at Key West
Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is NZ$467 per night from 30 Sep to 1 Oct
NZ$467
per night
30 Sep - 1 Oct
8.4/10 Very Good! (2,124 reviews)
"Great place to stay in key west. We had an oceanfront room with balcony. Room is big and comfortable. Beautiful view. Only downside was, there was construction at the sand bar and that was closed . We will be back."

Reviewed on 24 Sep. 2024

Southernmost Beach Resort
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$385 per night from 10 Oct to 11 Oct
NZ$385
per night
10 Oct - 11 Oct
8.4/10 Very Good! (1,796 reviews)
"Already booked again for next year! We love being able to walk across the street to the beach. The pool (and drinks) are very nice too!"

Reviewed on 24 Sep. 2024

Margaritaville Beach House Key West
See all 2,783 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.

Frequently asked questions

How much does a Key West holiday package cost?
Choose from any combination of car rentals, flights and hotels, and you can be holidaying in Key West from just . And the more you bundle, the more cash you save. Your dream escape has never been so affordable.
How do I get a cheap travel package to Key West?
Combine your flights and hotels, toss in extras such as a rental car or activities, and save with a Key West holiday package. You won’t just score exciting discounts on your adventure — you’ll have lots of choice too. When you book through Expedia, you’ll have your pick of over 550 partner airlines and 1 000 000 hotels across the globe. Your next epic adventure begins right here, right now!
Where should I stay in Key West?
A visit to Key West wouldn’t be complete without taking in the atmosphere in Old Town Key West, so why not secure a hotel room in this happening neighbourhood? That way, you’ll be right by Southernmost Point. If Mallory Square is on your must-see list, stay in Historic Seaport.
What are the top hotels in Key West?
Travellers visiting Key West often stay in Old Town Key West. Margaritaville Beach House Key West and Southernmost Beach Resort are preferred hotels in this neighbourhood. But it’s not the only fun place around town! Key West Historic District is another fantastic area and where you’ll find 24 North Hotel Key West and Oceans Edge Key West Resort, Hotel & Marina.
How far in advance should I book my Key West holiday?
Browse Expedia to compare international airfares ASAP. In most cases, you can purchase a ticket up to a year before departure. If it’s too early for your preferred air carrier, or you’ve left things to the last moment, fear not. Cheap fares to Key West sometimes occur a few weeks before the date of departure.
What does an Expedia Key West travel package include?
Flights, hotels and a cool set of wheels for your road trip adventures. Simply choose your favourite bundle and get access to great discounts. Once you’ve made your booking, add on a few tours and activities and watch your savings pile up. When it comes to crafting your Key West break, you’re the boss!
What should I know before booking a Key West travel package?
Locking in all the parts of your holiday together is a simple way to save. Combine car rentals, airfares and hotels into a handy package. But you’re not restricted to hotels. Expedia offers all types of properties, including holiday homes like mountain cabins and spacious residences. The list goes on!
Can I choose my airline with a Key West Expedia holiday package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines globally. Our packages give you the flexibility to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Key West holiday package?
It’s hard to predict what the future holds, so it’s comforting to know that you can cancel or change your Key West holiday package. If your booking was made in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for more information.

Discover the most popular places to visit in Key West

Image for Duval Street

Duval Street

5/5(5 reviews)

Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.

Duval Street
Image for Mallory Square

Mallory Square

4/5(3 reviews)

Enjoy the lively crowds, energetic performers and stunning sunset that make this city square the most popular meeting place in the evenings.

Mallory Square
Image for Smathers Beach

Smathers Beach

4/5(3 reviews)

Palm trees line the pristine white sands of this popular Key West beach where locals and visitors come to swim, sunbathe and play water sports.

Smathers Beach

What to do in Key West

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

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

NZ$54
Per adult
80% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Image for MIAMI: Key West Day Trip with Boating Options

MIAMI: Key West Day Trip with Boating Options

NZ$63
Per adult
MIAMI: Key West Day Trip with Boating Options
Image for Morning Coral Reef Snorkel With Mimosas & Breakfast

Morning Coral Reef Snorkel With Mimosas & Breakfast

NZ$75
Per adult
90% of travellers recommend
Morning Coral Reef Snorkel With Mimosas & Breakfast
See all activities in Key West

More holiday ideas

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