Key West Vacations from ￥499,638

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The Latest Key West Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
per person
Apr 16 - Apr 22
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Key West (EYW)
8.8/10 Excellent! (1,554 reviews)
Price especially the restaurant very pricey

Reviewed on Feb 21, 2025

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
per person
Apr 16 - Apr 22
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Key West (EYW)
9.8/10 Exceptional! (1,001 reviews)
The staff is absolutely incredible. Neal, Trudy and Chris are awesome. I will stay here every time I come to key West

Reviewed on Feb 12, 2025

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Old Town Key West
per person
Apr 16 - Apr 22
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Key West (EYW)
10/10 Exceptional! (1,001 reviews)
Great place to stay. Just off Duval Street and ideally situated for everything. Very helpful staff, clean, decent pool area, happy hour and great breakfast. Wish we could have stayed longer.

Reviewed on Feb 21, 2025

Douglas House

Douglas House

3 out of 5
Old Town Key West
per person
Apr 16 - Apr 22
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Key West (EYW)
9.4/10 Exceptional! (13 reviews)
Walking distance to loads of bars and restaurants

Reviewed on Feb 17, 2025

Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Old Town Key West
per person
Apr 16 - Apr 22
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
Definitely would return

Reviewed on Feb 20, 2025

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 Historic District

Old Town Key West

4 out of top 10 points of interest in this area
4.5/5(226 area reviews)

Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.

Find hotels in Old Town Key West

Find the Best Key West Vacation Packages

Key West Hotel Deals

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 ￥64,820 per night from Feb 25 to Feb 26
￥64,820
￥82,998 total
includes taxes & fees
Feb 25 - Feb 26
8.6/10 Excellent! (2,271 reviews)
"From the check in process to the check out process, it was an absolute perfect stay at this resort. The staff was exceptionally delightful, kind and professional! The grounds were clean, well maintained and what you would envision on your Key West tropical vacation. The location was right on famous ..."

Reviewed on Feb 18, 2025

Southernmost Beach Resort
Oceans Edge Key West Resort, Hotel & Marina
Oceans Edge Key West Resort, Hotel & Marina
4 out of 5
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
The price is ￥59,223 per night from Feb 23 to Feb 24
￥59,223
￥75,690 total
includes taxes & fees
Feb 23 - Feb 24
8.8/10 Excellent! (1,562 reviews)
"Staff wear lovely! Bartenders and servers were exrtemley nice and accomodating. The fres seafood was excellent and far beyond our expectations for a a hotel bar/cafe! So much so that we made it a point to eat there once a day to try everything. Rooms were clean, large and comfortable with a nice ..."

Reviewed on Feb 19, 2025

Oceans Edge Key West Resort, Hotel & Marina
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 ￥50,752 per night from Feb 26 to Feb 27
￥50,752
￥64,654 total
includes taxes & fees
Feb 26 - Feb 27
8.4/10 Very Good! (1,014 reviews)
"Parking located under our room.very close to pool and beach with stairs from our porch to beach area. Pool bar and restaurant very convenient and prompt staff. Definitely will be back"

Reviewed on Feb 21, 2025

Beachside Resort & Residences
See all 2,888 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 vacation package cost?
Offering excellent value package deals from ￥499,638 on Expedia, you’ll be pleasantly surprised at how much a vacation 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 vacation 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 vacations 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 neighborhoods 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 vacation package to Key West?
Key West offers everything you need for an amazing trip. Begin your Key West vacation 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 personalize 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 vacation as a package?
Expedia vacation 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 personalized Key West vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation 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 favorite 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 vacation. 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 personalized Key West vacation package.

Discover the most popular places to visit in Key West

Duval Street featuring signage

Duval Street

4.5/5(3,475 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
Mallory Square which includes a sunset and a bay or harbor as well as a large group of people

Mallory Square

4.5/5(3,096 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 featuring signage as well as a large group of people

Southernmost Point

4.5/5(3,182 reviews)

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

Southernmost Point

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

￥7,463
per adult
80% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
12-Hours Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

￥7,463
per adult
Full Day Trip in Key West from Miami
Aerial view of people snorkeling in Key West

Morning Coral Reef Snorkel With Mimosas & Breakfast

￥6,299
per adult
92% of travellers recommend
Morning Coral Reef Snorkel With Mimosas & Breakfast
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.