Historic Seaport Vacation Packages

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Top Holiday Package Deals in Historic Seaport

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
Price was CA $1,563, price is now CA $1,293 per person
CA $1,293
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (1,874 reviews)
The property was well maintained and the house keeping was excellent.

Reviewed on Jun 14, 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was CA $2,910, price is now CA $2,249 per person
CA $2,249
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (559 reviews)
We loved staying here and highly recommended it. Only thing that people might not like is the solo musicians play till 11pm every night. We didn’t mind it since we are not early birds.

Reviewed on Jun 7, 2026

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

3 out of 5
Key West Historic District
Price was CA $3,056, price is now CA $2,485 per person
CA $2,485
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
No reviews
Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Old Town Key West
Price was CA $2,637, price is now CA $2,155 per person
CA $2,155
per person
Sep 4 - Sep 8
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (194 reviews)
This was a great place to stay! Clean and well-placed on Key West. Pool and patio were great for getting some sun.

Reviewed on May 29, 2026

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Old Town Key West
Price was CA $1,775, price is now CA $1,478 per person
CA $1,478
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (380 reviews)
Great location, wonderful room, great pool, and great views. Lacking services: no shuttle, no restaurant, you pay resort fees per night but no amenities? We feel like they used the bait and switch on us, great reservation price on room but hit you with nightly fees once you get there. That was our only real negative

Reviewed on Jun 16, 2026

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
Old Town Key West

Old Town Key West

3 out of top 10 points of interest in this area
3.5/5(8 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

Historic Seaport Hotel Deals

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 $263 per night from Jul 8 to Jul 9
CA $263
CA $343 total
Jul 8 - Jul 9
includes taxes & fees
9/10 Wonderful! (425 reviews)
"Good🤗"

Reviewed on Jun 18, 2026

La Concha Key West, Autograph Collection
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 $361 per night from Jun 29 to Jun 30
CA $361
CA $504 total
Jun 29 - Jun 30
includes taxes & fees
9/10 Wonderful! (1,182 reviews)
"Awesome place to stay. Fun amenities, great staff. Cold AC. Convenient. Excellent!"

Reviewed on Jun 18, 2026

Pier House Resort & Spa
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 $332 per night from Jun 29 to Jun 30
CA $332
CA $472 total
Jun 29 - Jun 30
includes taxes & fees
9/10 Wonderful! (1,012 reviews)
"We had the most amazing experience specially at the bar with Amber was amazing. She knew exactly what my pup wanted shaking but not stir."

Reviewed on Jun 16, 2026

Hyatt Centric Key West Resort and Spa
See all 2,704 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 $1,293, 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.

Discover the most popular places to visit in Historic Seaport

Mallory Square

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
Key West Shipwreck Museum

Key West Shipwreck Museum

This interactive museum is home to unbelievable relics pulled from the bottom of the sea and a watchtower with views across the Gulf of Mexico.

Key West Shipwreck Museum

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $62
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 $36
per child
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Snorkler waving underwater in Key West

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

CA $76
per adult
86% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
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.