Historic Seaport Vacations from $966

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Your Historic Seaport Vacation

Make travel planning hassle-free by creating a vacation package to Historic Seaport. We'll look after the minutiae, so you can concentrate on soaking up everything this neighborhood can offer. Can't wait to head out and see the sights during your trip to Historic Seaport? Be sure to check out nearby attractions like Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Expedia can put your plans into action. Book your ultimate Historic Seaport vacation now.

The Latest Historic Seaport Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West
Save 100% on your flight
$966
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (414 reviews)
The Key West Hotel

The Key West Hotel

Key West Historic District
$2,907
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (562 reviews)
Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
$1,758
per person
Nov 21 - Nov 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,003 reviews)
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

Old Town Key West
$1,741
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (493 reviews)
Perfect location, quiet, but a short walk to everything fun. And I. August heat in the Keys, the only walks must be short. Cottages are small but well laid out, with super comfy bed, cold AC and hotter than hot shower. Staff was awesome and the 3 pm happy hour by the pool was laid back. Breakfast wasn't fancy, but it was abundant. We will definitely be back.

Reviewed on Aug 29, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
$2,025
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)
Super nice and clean, staff was wonderful w knowledge of the history of the mansion

Reviewed on Aug 24, 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
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
A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

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.

Find hotels in Downtown Key West
A two-story house with green shutters and a wooden balcony.

Key West Historic District

2 out of top 10 points of interest in this area

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.

Find hotels in Key West Historic District
A marina with yachts docked, a prominent red building, and a coastal cityscape in the background.

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 Key West Tropical Forest and Botanical Garden.

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A sunset over the ocean with scattered clouds.

Uptown - Upper Duval

If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.

Find hotels in Uptown - Upper Duval

Historic Seaport Hotel Deals

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

601 Front St Key West FL
Fully refundableReserve now, pay when you stay
$263 nightly
$296 total
Sep 29 - Sep 30
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"Loved the location overall 100%"

Reviewed on Aug 29, 2026

Hyatt Centric Key West Resort and Spa
Pier House Resort & Spa

Pier House Resort & Spa

1 Duval St Key West FL
Fully refundableReserve now, pay when you stay
$310 nightly
$349 total
Sep 9 - Sep 10
Total with taxes and fees
9/10 Wonderful! (1,307 reviews)
"Best Hotel in the Key West. Room was very clean, best staff services. Beautiful beach view and breakfast was delicious. My husband and I love this place. 💯 recommend."

Reviewed on Aug 30, 2026

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

La Concha Key West, Autograph Collection

430 Duval St Key West FL
Fully refundableReserve now, pay when you stay
$219 nightly
$246 total
Sep 1 - Sep 2
Total with taxes and fees
La Concha Key West, Autograph Collection
See all 2,692 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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All Inclusive Vacations
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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.
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A historic building with a tall tower, palm trees, and a vintage trolley.

Key West Shipwreck Museum

8.6/10 (361 reviews)
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.
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A two-story house with green shutters and a wooden balcony.

Audubon House and Tropical Gardens

8.8/10 (378 reviews)
Visit a house named after famed naturalist John James Audubon. Learn the history of why the house came to be here.
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Sails To Rails Museum at Flagler Station

You can spend time studying the exhibits at Sails To Rails Museum at Flagler Station in Key West. Stroll along the beautiful beaches or seek out the biking trails.
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Key West Historic Seaport

Find out about the history of Key West with a stop at Key West Historic Seaport. Discover the area's lively bars and its great live music.
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Schooner Western Union

8.0/10 (1 review)
Learn about the local history of Key West when you spend time at Schooner Western Union. Stroll along the area's seaside or experience its lively festivals.
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Donkey Milk House

7.4/10 (6 reviews)
You can spend an afternoon exploring the galleries in Donkey Milk House during your trip to Key West. Discover the area's beautiful sunsets, or seek out its biking trails.
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Waterfront Playhouse

8.4/10 (7 reviews)
You can enjoy a show at Waterfront Playhouse during your trip to Key West. Wander the seaside and beautiful beaches in the area.
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Things to do

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

$69
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
Miami to Key West Day Trip with Activity Options

Miami to Key West Day Trip with Activity Options

$39
per adult
84% of travellers recommend
Miami to Key West Day Trip with Activity Options
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.