Deals on vacations and trips to Historic Seaport

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Historic Seaport flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Old Town Key West
Price was $1,243, price is now $912 per person
$912
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool and a hot tub. Enjoy the free self-serve breakfast each morning. Self parking, a terrace, and a garden are also offered.
The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $3,351, price is now $2,278 per person
$2,278
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $4,782, price is now $3,273 per person
$3,273
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

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

3 out of 5
Old Town Key West
Save 100% on your flight
Price was $4,687, price is now $3,410 per person
$3,410
per person
Dec 1 - Dec 7
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas.
Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5
Old Town Key West
Save 100% on your flight
Price was $4,159, price is now $3,051 per person
$3,051
per person
Dec 1 - Dec 7
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas and barbecue grills.

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
$308 nightly
The price is $346 total per night
$346 total
Sep 28 - Sep 29
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.
On private beach
Pool
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
$287 nightly
The price is $323 total per night
$323 total
Sep 21 - Sep 22
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.
Pool
Spa
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
$219 nightly
The price is $246 total per night
$246 total
Sep 21 - Sep 22
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.
Pool
Pet friendly
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
$328 nightly
The price is $369 total per night
$369 total
Sep 28 - Sep 29
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.
Pool
Spa
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
200 William Street Key West FL
Free Cancellation
$245 nightly
The price is $276 total per night
$276 total
Sep 27 - Sep 28
Total with taxes and fees
This smoke-free hotel features 3 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Pool
Pet friendly
Eden House

Eden House

4 out of 5
1015 Fleming St Key West FL
$142 nightly
The price is $160 total per night
$160 total
Sep 21 - Sep 22
Total with taxes and fees
This hotel features an outdoor pool, a hot tub, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. There's a poolside bar on site, and concierge services and wedding services are also provided.
Pool
Hot Tub
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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.

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

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 $912. 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.