Key West Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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
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Key West Historic District

4 out of top 10 points of interest in this area
4.5/5(66 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 hotels in Key West Historic District

Top hotels in Key West

Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is S$459 per night from 17 Dec to 18 Dec
S$459
includes taxes & fees
17 Dec - 18 Dec
8.4/10 Very Good! (2,180 reviews)
"No me gustó q en expedia no explicara q no incluya el estacionamiento"

Reviewed on 20 Nov,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
The price is S$394 per night from 19 Dec to 20 Dec
S$394
includes taxes & fees
19 Dec - 20 Dec
8.6/10 Excellent! (1,782 reviews)
"Quality place"

Reviewed on 22 Nov,2024

Margaritaville Beach House Key West
Havana Cabana at Key West - Adults Only
Havana Cabana at Key West - Adults Only
4 out of 5
3420 N. Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is S$294 per night from 18 Dec to 19 Dec
S$294
includes taxes & fees
18 Dec - 19 Dec
8.8/10 Excellent! (1,601 reviews)
"Great property!!!"

Reviewed on 23 Nov,2024

Havana Cabana at Key West - Adults Only
See all 2,806 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 rentals 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.

Popular places to visit

Mallory Square

Mallory Square

4/5(36 reviews)

Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.

Mallory Square
Southernmost Point

Southernmost Point

4/5(39 reviews)

Snap a memorable photograph from the edge of North America at this monumental landmark.

Southernmost Point
Smathers Beach showing a sandy beach, a luxury hotel or resort and tropical scenes

Smathers Beach

4/5(10 reviews)

Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.

Smathers Beach

What to do in Key West

12 hours Day at Key West With Boat Tour and Snorkeling

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

S$44
Per adult
80% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
MIAMI: Key West Day Trip with Boating Options

MIAMI: Key West Day Trip with Boating Options

S$158
Per adult
MIAMI: Key West Day Trip with Boating Options
12-Hours Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

S$43
Per adult
Full Day Trip in Key West from Miami
See all activities in Key West

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.