Key West Historic District Vacations from ￥347,906

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The Latest Key West Historic District Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was ￥483,567, price is now ￥347,906 per person
￥347,906
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Loved the location, room was nice, bathroom very small, very friendly staff, slow service at restaurant in the morning. Will go back

Reviewed on Feb 24, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was ￥5,571,062, price is now ￥2,721,749 per person
￥2,721,749
per person
Apr 29 - May 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8/10 Very Good! (1 review)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was ￥596,394, price is now ￥405,922 per person
￥405,922
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8/10 Very Good! (1,120 reviews)
Staff are great but the bed and pillows were uncomfortable. Especially the pillows they are horrible. I had to use a towel as my pillow. Other hotels have feather pillows that are far more comfortable. It would be nice to have a choice. For this reason we won’t return. It’s too bad because everything else was nice.

Reviewed on Feb 19, 2026

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was ￥486,183, price is now ￥353,314 per person
￥353,314
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
It was perfect. It was right across from the beach lots of shops lots of restaurants lovely area.

Reviewed on Feb 24, 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was ￥484,422, price is now ￥352,580 per person
￥352,580
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
Staff was very friendly and great locations. The rooms were decent for the price but did have a mild funky aroma. I guess that can expected when you are in such a humid hot environment..

Reviewed on Feb 24, 2026

Where to stay in Key West Historic District

Find the best Key West Historic District areas and neighborhoods for the activities you enjoy most. Learn more about Key West Historic District
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

Key West Historic District Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
The price is ￥72,428 per night from Mar 5 to Mar 6
￥72,428
￥92,884 total
Mar 5 - Mar 6
includes taxes & fees
8.8/10 Excellent! (3,109 reviews)
Everything was A+. Room, pool, cafe, staff for all areas.

Reviewed on Feb 25, 2026

Southernmost Beach Resort and Guesthouses
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
601 Front St Key West FL
Fully refundableReserve now, pay when you stay
The price is ￥65,877 per night from Mar 22 to Mar 23
￥65,877
￥84,898 total
Mar 22 - Mar 23
includes taxes & fees
9/10 Wonderful! (1,013 reviews)
Excellent location, clean and luxurious room. Restaurant on premises was amazing.

Reviewed on Feb 24, 2026

Hyatt Centric Key West Resort and Spa
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 ￥111,769 per night from Mar 8 to Mar 9
￥111,769
￥136,264 total
Mar 8 - Mar 9
includes taxes & fees
8.4/10 Very Good! (556 reviews)
All was great staff, room cleanliness. But one thing we were very disappointed in was the fact that one of our beach days we did not have a beach chair!! So disappointing for the price we pay that you don’t have enough beach chairs and we had to sit on the ground.

Reviewed on Feb 25, 2026

Casa Marina Key West, Curio Collection by Hilton
See all 1,702 properties in Key West Historic District
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 Historic District vacation package cost?
Less than you might think — from a low ￥347,906, actually! By combining flights, hotels and car rentals into a custom-built vacation package, your Key West Historic District escape is just a few clicks away.
How do I get a cheap travel package to Key West Historic District?
Book everything in the one place with our Key West Historic District vacation packages. We have deals on flights, hotels, tours and more that'll keep your pocketbook happy and adventurous side satisfied. And, with more than 550 airlines and 1,000,000 hotel options throughout the world to choose from, you'll have the flexibility to mix and match as you want.
Where should I stay in Key West Historic District?
Travelers come from far and wide to experience Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens in Key West Historic District. Book yourself a room within a stone's throw of these must-see attractions to make sightseeing easy.
What are the top hotels in Key West Historic District?
Secure a room at Southernmost Retreat: 2 Blocks From Duval In Old Town. It's one of the area's most sought-after hotels. Another top option in Key West Historic District is Walk to Duval Waterfront Marina View 2-Bed Galleon + Beach + Sunset Tiki Bar.
How far in advance should I book my Key West Historic District vacation?
Savvy travelers book early. Air carriers typically release flights up to 12 months ahead of departure, and this is an excellent opportunity to pick up some of the lowest prices. Just been told you need to take some vacation time next week? Don't fret. Expedia are never short of fantastic deals to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Key West Historic District travel package include?
Hotels, flights and a cool set of wheels for your road trip adventures. Simply select your preferred bundle and get access to incredible deals. Once you've made your booking, add on a few sightseeing tours and watch your savings stack up. When it comes to creating your Key West Historic District break, you're in control!
What should I know before booking a Key West Historic District travel package?
You'll enjoy amazing savings when you combine your flights, hotels and rental cars into a travel package. Plus, booking everything together will make your trip planning easier. So why waste time or money? Whether you're putting together a ritzy romantic getaway or a budget solo adventure, check out our vacation packages today.
Can I choose my airline with a Key West Historic District Expedia vacation package?
Yes, and with more than 550 airlines to select from across the globe, you have loads of choice. Look through the available options and see which airline suits your needs and budget.
If I'm not able to travel, can I cancel my Key West Historic District vacation package?
If your vacation plans in Key West Historic District have changed, it's a relief to know that it's possible to cancel your booking. If your booking was made less than 24 hours ago, you may be eligible for a refund. If your booking is older than that, your hotel, airline or car rental company may charge fees. To learn more, check our Customer Service Portal.

Discover the most popular places to visit in Key West Historic District

Duval Street featuring signage

Duval Street

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

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
Ernest Hemingway Home and Museum featuring heritage elements and a house

Ernest Hemingway Home and Museum

Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.

Ernest Hemingway Home and Museum

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

￥6,958
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Friends cheers with cocktails on Key West cruise

Key West Afternoon At The Reef Snorkeling Adventure with Open Bar!

￥7,376
per adult
92% of travellers recommend
Key West Afternoon At The Reef Snorkeling Adventure with Open Bar!
GLASS BOTTOM BOAT

Miami to Key West Day Trip with Activity Options

￥6,036
per adult
80% of travellers recommend
Miami to Key West Day Trip with Activity Options
See all activities in Key West

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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.