Deals on vacations and trips to Historic Seaport

Choose two or more items and save on your trip:

Historic Seaport flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $837, price is now $612 per person
$612
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a 24-hour gym.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Price was $950, price is now $653 per person
$653
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool and free perks like continental breakfast and WiFi in public areas.
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Price was $1,305, price is now $933 per person
$933
per person
Sep 6 - Sep 11
found 24 hours ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-in.
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $1,754, price is now $1,255 per person
$1,255
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.
The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,545, price is now $1,142 per person
$1,142
per person
Sep 6 - Sep 11
found 24 hours ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
2 outdoor pools, 2 bars/lounges, and a restaurant are among this bed & breakfast's featured amenities. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the poolside bar and enjoy the free cooked-to-order breakfast each morning.

Top Historic Seaport hotels deals

Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
Free Cancellation
Reserve now, pay when you stay
$328 nightly
The price is $369 total per night
$369 total
Jul 6 - Jul 7
Total with taxes and fees
This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-in.
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
430 Duval St Key West FL
Free Cancellation
Reserve now, pay when you stay
$216 nightly
The price is $243 total per night
$243 total
Jul 13 - Jul 14
Total with taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
601 Front St Key West FL
Free Cancellation
Reserve now, pay when you stay
$261 nightly
The price is $294 total per night
$294 total
Jul 13 - Jul 14
Total with taxes and fees
This smoke-free resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.
Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

4 out of 5
Zero Duval St. Key West FL
Free Cancellation
Reserve now, pay when you stay
$493 nightly
The price is $555 total per night
$555 total
Jul 12 - Jul 13
Total with taxes and fees
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the 24-hour gym and visit the 3 bars/lounges and poolside bar for drinks.
NYAH Key West - Adults Only

NYAH Key West - Adults Only

3 out of 5
420 Margaret Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $133 total per night
$133 total
Jul 1 - Jul 2
Total with taxes and fees
This guesthouse's 3 outdoor pools and a rooftop terrace are among the featured amenities. Enjoy the hot tub and free continental breakfast each morning. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Bishop Hotel Key West

Bishop Hotel Key West

4 out of 5
822 Fleming St Key West FL
Get rates
This guesthouse's 2 outdoor pools and hot tub are among the featured amenities. Unwind with a drink at the poolside bar and enjoy perks like free continental breakfast and free WiFi. There's luggage storage and multilingual staff can provide around-the-clock assistance.
Don't see what you're looking for?
See all available properties in Historic Seaport
View all properties
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.

Popular places to visit

A crowded waterfront promenade with people walking and sitting, palm trees, and a sunset over the ocean.

Mallory Square

4.5/5(3,147 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.

Mallory Square
A historic building with a tall tower, palm trees, and a vintage trolley.

Key West Shipwreck Museum

4/5(326 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.

Key West Shipwreck Museum
Key West Aquarium, a white building with a red roof, and a wooden pier extending into turquoise water.

Key West Aquarium

4/5(383 reviews)

Come face to face with huge sharks, feed stingrays and learn about local tropical fish at this great aquarium.

Key West Aquarium

Frequently asked questions

How much are vacation packages to Historic Seaport?
Treat yourself to a one-of-a-kind experience in Historic Seaport with a vacation package starting from as low as $612. Reserving your tours, flights and hotels with Travelocity is easy. What's more, our vacation deals will leave you with more savings for plenty of fun activities.
Where can I get the best vacation package deals for Historic Seaport?
It's hard to top Travelocity when it comes to crafting your Historic Seaport package deal. There are as many as 400 air carriers and 1,000,000 properties around the world to select from. Book your vacation now and get ready to tick another exciting place off your must-visit list.
Why should I book my Historic Seaport vacation bundle with Travelocity?
From incredible destinations to one-of-a-kind experiences, we have everything you need to satisfy your love for travel. Our 24/7 support will also ensure you're being well taken care of while you're on your trip. And don't fret if you notice a cheaper price on your reservation, we'll match it. That's our Price Match Guarantee.
Can I save on my Historic Seaport car rental if I combine it with a hotel or flight?
Bundling your bookings into a Historic Seaport vacation package will certainly save you money. Combine a flight and car; a hotel, car and flight; or a hotel and car. You won't find a better way to discover the greater Historic Seaport area than with your own ride. You can also add experiences and activities to your Travelocity package.

Photos of local treasures

Browse Historic Seaport vacation photos for more inspiration

A pier with people dining under umbrellas, a sailboat in the distance, and a sunset over the water.
Two sailboats on the ocean with a sunset in the background.
A marina with boats docked, a waterfront restaurant named 'The Commodore Restaurant', and a sign indicating 'Harbor'.
A waterfront promenade with rows of sun loungers and palm trees.
A waterfront event with a crowd watching a performance.