Deals on vacations and trips to Historic Seaport
Historic Seaport flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Windward Pointe, Key West
Price was $1,516, price is now $1,047 per person
$1,047
per person
Jun 12 - Jun 15
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, concierge services, and barbecue grills are also on offer.
The Key West Hotel
Key West Historic District
Price was $2,305, price is now $1,629 per person
$1,629
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop 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.
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Save 100% on your flight
Price was $3,505, price is now $2,508 per person
$2,508
per person
Jun 1 - Jun 8
found 7 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas.
Orchid Key Inn - Adults Only
Old Town Key West
Save 100% on your flight
Price was $1,637, price is now $1,179 per person
$1,179
per person
May 24 - May 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the hot tub and free continental breakfast each morning. Self parking, a garden, and dry cleaning are also offered.
The Marker Key West Harbor Resort
Key West Historic District
Save 100% on your flight
Price was $1,674, price is now $1,212 per person
$1,212
per person
May 24 - May 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
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.
Top Historic Seaport hotels deals
Pier House Resort & Spa
1 Duval St Key West FL
Free Cancellation
Reserve now, pay when you stay
The price is $678 total per night
$678 total
per night
Apr 12 - Apr 13
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
NYAH Key West - Adults Only
420 Margaret Street Key West FL
Free Cancellation
Reserve now, pay when you stay
The price is $268 total per night
$268 total
per night
Mar 23 - Mar 24
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.
Pool
Hot Tub
Ocean Key Resort - A Noble House Resort
Zero Duval St. Key West FL
The price is $583 total per night
$583 total
per night
Apr 12 - Apr 13
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
Hyatt Centric Key West Resort and Spa
601 Front St Key West FL
Free Cancellation
Reserve now, pay when you stay
The price is $551 total per night
$551 total
per night
Apr 12 - Apr 13
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
Eden House
1015 Fleming St Key West FL
The price is $483 total per night
$483 total
per night
Mar 31 - Apr 1
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
The Marker Key West Harbor Resort
200 William Street Key West FL
Free Cancellation
Reserve now, pay when you stay
The price is $628 total per night
$628 total
per night
Mar 22 - Mar 23
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
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See all available properties in Historic Seaport
View all propertiesLowest 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
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.
Key West Aquarium
Come face to face with huge sharks, feed stingrays and learn about local tropical fish at this great aquarium.
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.
Frequently asked questions
Photos of local treasures
Browse Historic Seaport vacation photos for more inspiration
