A pier with people dining under umbrellas, a sailboat in the distance, and a sunset over the water.

Historic Seaport Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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The Latest Historic Seaport Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 28 - Jan 2

    Blue Flamingo Resort Key West + Flight

    New Town
    5 nights
    4.0 star property
    8.6/10 - Excellent (2,783 reviews)
    "The room was clean & comfortable and had a waterfront view but you had to look past the hustle & bustle of US 1. The room was surprisingly quiet given the road noise. The resort was charming and had 2 pools. Resort could provide some more pool floaties for those that love relax in the pool. Perhaps those with cup holders for the fabulous drinks! There are lots of activities in "The Backyard" like bocce, foosball, shuffleboard, ping pong, giant chess, a putting green and even a converted..."
    Reviewed November 9, 2026
    Roundtrip • Detroit (DTW) - Key West (EYW)
    DTW - MIA • Nonstop MIA - DTW • 1 stop
    CA $3,466
    CA $2,509
    per traveller
    found 7 hours ago
    Blue Flamingo Resort Key West
  • Dec 28 - Jan 2

    The Key West Hotel + Flight

    Key West Historic District
    5 nights
    3.0 star property
    9.2/10 - Wonderful (565 reviews)
    "Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!"
    Reviewed October 29, 2026
    Roundtrip • Detroit (DTW) - Key West (EYW)
    DTW - MIA • Nonstop MIA - DTW • 1 stop
    CA $6,178
    CA $3,954
    per traveller
    found 7 hours ago
    The Key West Hotel
  • Dec 28 - Jan 2

    Southernmost House - Adult Exclusive + Flight

    Old Town Key West
    5 nights
    4.0 star property
    9.4/10 - Exceptional (1,003 reviews)
    Roundtrip • Detroit (DTW) - Key West (EYW)
    DTW - MIA • Nonstop MIA - DTW • 1 stop
    CA $5,596
    CA $4,000
    per traveller
    found 7 hours ago
    Southernmost House - Adult Exclusive
  • Jan 10 - Jan 16

    Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool! + Flight

    Old Town Key West
    6 nights
    3.0 star property
    10/10 - Exceptional (1 review)
    "Loved the closeness to Duval st and the privacy "
    Reviewed October 17, 2025
    Roundtrip • Toronto (YYZ) - Key West (EYW)
    YYZ - EYW • 1 stop EYW - YYZ • 1 stop
    CA $7,722
    CA $5,520
    per traveller
    found 1 hour ago
    Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
  • Dec 28 - Jan 2

    The Marker Key West Harbor Resort + Flight

    Key West Historic District
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,046 reviews)
    Roundtrip • Detroit (DTW) - Key West (EYW)
    DTW - MIA • Nonstop MIA - DTW • 1 stop
    CA $6,384
    CA $4,637
    per traveller
    found 7 hours ago
    The Marker Key West Harbor Resort

Where to stay in Historic Seaport

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

Old Town Key West

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.

Downtown Key West

If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.

Key West Historic District

Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.

New Town

Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Fort East Martello Museum and Gallery.

Discover the most popular places to visit in Historic Seaport

What to do near Historic Seaport

Historic Seaport Hotel Deals

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 Historic Seaport vacation package cost?

Our Historic Seaport vacation packages, which begin at just CA $2,509, are the easiest way to save. Handpick your preferred flights, hotels and rental cars to create your perfect trip.

How do I get a cheap travel package to Historic Seaport?

One of the easiest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we've got everything you need. Choose a combination that suits you and see your savings pile up. Of course, a package deal is never a one-size-fits-all. That's why we offer over 550 partner airlines and 1,000,000 properties globally, which lets you customize your Historic Seaport adventure.

Where should I stay in Historic Seaport?

Take the leg work out of sightseeing by staying just around the corner from Historic Seaport's fantastic attractions. Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens are two which top many visitors' bucket lists.

What are the top hotels in Historic Seaport?

Curry House and Ocean Key Resort - A Noble House Resort are among the most well-known properties in Historic Seaport. Why not take a look at the amenities and facilities at each and then decide?

How far in advance should I book my Historic Seaport vacation?

While not all air carriers release ticket prices early, you can usually compare international airfares on Expedia up to a year in advance. This is when you'll nab some incredible deals. If you're purchasing tickets last minute, you may still be in luck. Sometimes the cheapest prices become available just weeks prior to departure.

What does an Expedia Historic Seaport travel package include?

With Expedia, you can choose any combination of flights, car rentals and hotels to build your ideal Historic Seaport package. Once you've made your booking, you can add on the fun things like activities and tours. Remember — the more you bundle, the greater the savings!

What should I know before booking a Historic Seaport travel package?

So many places to wander around, so many things to see and do. With a travel package, you'll be able to cross more of them off your list. Bundle your flights, hotels and rental cars and get ready to save.

Can I choose my airline with a Historic Seaport Expedia vacation package?

With a vacation package, you're the boss. Whether you're looking to fly to Historic Seaport in coach or business class, simply pick from the available airline options. Expedia has access to more than 550 partner airlines all over the world.

If I'm not able to travel, can I cancel my Historic Seaport vacation package?

Don't worry if you're rethinking your Historic Seaport vacation package — it's possible to cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We know your circumstances can suddenly change, so make your way to our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.

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