Historic Seaport Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Historic Seaport

Price found within the past 48 hours. Click for updated prices.
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
New Town
Price was CA $1,702, price is now CA $1,423 per person
CA $1,423
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
8.4/10 Very good! (2,566 reviews)

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was CA $6,089, price is now CA $3,869 per person
CA $3,869
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
9.2/10 Wonderful! (561 reviews)
This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!

Reviewed on Jul 27, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Price was CA $3,926, price is now CA $2,838 per person
CA $2,838
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (1,005 reviews)
Great location and nice historic home

Reviewed on Aug 1, 2026

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
Key West Historic District
Price was CA $3,695, price is now CA $3,034 per person
CA $3,034
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
9/10 Wonderful! (440 reviews)
Loved the DJ at night in the lobby. Amazing time dancing.

Reviewed on Aug 4, 2026

Fitch Lodge - Key West Historic Inns

Fitch Lodge - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was CA $1,871, price is now CA $1,546 per person
CA $1,546
per person
Oct 19 - Oct 22
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
8.8/10 Excellent! (635 reviews)

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
A white building with shutters, palm trees, and a lawn.

Old Town Key West

4 out of top 10 points of interest in this area

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

Historic Seaport Hotel Deals

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 CA $280 per night from Aug 10 to Aug 11
CA $280
CA $412 total
Aug 10 - Aug 11
includes taxes & fees
Hyatt Centric Key West Resort and Spa
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $353 per night from Aug 20 to Aug 21
CA $353
CA $495 total
Aug 20 - Aug 21
includes taxes & fees
9/10 Wonderful! (1,262 reviews)
"Check-in was quick and easy, loved the wristbands as the room keys! The room was clean, nicely decorated, and had a huge bathroom (Junior Spa Suite). Beach was on the smaller side, but adequate, pool was also small. Staff were friendly and helpful!"

Reviewed on Aug 4, 2026

Pier House Resort & Spa
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
430 Duval St Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $274 per night from Aug 18 to Aug 19
CA $274
CA $356 total
Aug 18 - Aug 19
includes taxes & fees
9/10 Wonderful! (459 reviews)
"Loved the DJ at night in the lobby. Amazing time dancing."

Reviewed on Aug 4, 2026

La Concha Key West, Autograph Collection
See all 2,700 properties in Historic Seaport
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.
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Frequently asked questions

How much does a Historic Seaport vacation package cost?
Our Historic Seaport vacation packages, which begin at just CA $1,423, 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.

Stay near popular Historic Seaport attractions

A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.

Mallory Square

9.2/10 (15,939 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.
See properties

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $63
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $78
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

CA $111
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
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.