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
Save 100% on your flight
Price was $1,264, price is now $835 per person
$835
per person
May 31 - Jun 3
found 1 day 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
Save 100% on your flight
Price was $1,531, price is now $960 per person
$960
per person
May 31 - Jun 3
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.
Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
Price was $2,121, price is now $1,369 per person
$1,369
per person
May 10 - May 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free.
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Save 100% on your flight
Price was $3,573, price is now $2,452 per person
$2,452
per person
Jun 2 - Jun 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas.
Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays
Old Town Key West
Save 100% on your flight
Price was $3,511, price is now $2,504 per person
$2,504
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool is 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
$609 nightly
The price is $685 total per night
$685 total
Mar 25 - Mar 26
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
NYAH Key West - Adults Only
420 Margaret Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$253 nightly
The price is $285 total per night
$285 total
Mar 31 - Apr 1
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.
Pool
Hot Tub
Ocean Key Resort - A Noble House Resort
Zero Duval St. Key West FL
Free Cancellation
Reserve now, pay when you stay
$519 nightly
The price is $583 total per night
$583 total
Apr 12 - Apr 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.
Pool
Spa
Hyatt Centric Key West Resort and Spa
601 Front St Key West FL
Free Cancellation
Reserve now, pay when you stay
$490 nightly
The price is $551 total per night
$551 total
Apr 12 - Apr 13
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
Eden House
1015 Fleming St Key West FL
$430 nightly
The price is $483 total per night
$483 total
Mar 31 - Apr 1
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
The Marker Key West Harbor Resort
200 William Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$559 nightly
The price is $628 total per night
$628 total
Mar 22 - Mar 23
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
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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
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