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 $1,436, price is now $1,001 per person
$1,001
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip 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 $2,092, price is now $1,322 per person
$1,322
per person
Apr 16 - Apr 19
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 Beach House, Key West
Save 100% on your flight
Price was $1,761, price is now $1,192 per person
$1,192
per person
Apr 19 - Apr 24
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool and a hot tub. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A safe deposit box and concierge services are also provided.
Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay
Beachside
Save 100% on your flight
Price was $3,854, price is now $2,701 per person
$2,701
per person
Apr 8 - Apr 15
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.
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Old Town Key West
Save 100% on your flight
Price was $3,143, price is now $2,227 per person
$2,227
per person
Apr 8 - Apr 15
found 1 day 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 and barbecue grills.
Top Historic Seaport hotels deals
La Concha Key West, Autograph Collection
430 Duval St Key West FL
$499 nightly
The price is $561 total per night
$561 total
Feb 1 - Feb 2
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.
Pier House Resort & Spa
1 Duval St Key West FL
$559 nightly
The price is $629 total per night
$629 total
Jan 28 - Jan 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.
NYAH Key West - Adults Only
420 Margaret Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$286 nightly
The price is $322 total per night
$322 total
Jan 29 - Jan 30
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.
Ocean Key Resort - A Noble House Resort
Zero Duval St. Key West FL
Free Cancellation
Reserve now, pay when you stay
$632 nightly
The price is $712 total per night
$712 total
Jan 28 - Jan 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.
The Marker Key West Harbor Resort
200 William Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$502 nightly
The price is $564 total per night
$564 total
Jan 28 - Jan 29
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.
Hyatt Centric Key West Resort and Spa
601 Front St Key West FL
Free Cancellation
Reserve now, pay when you stay
$601 nightly
The price is $676 total per night
$676 total
Jan 28 - Jan 29
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.
Don't see what you're looking for?
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
4.5/5(3,096 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.
Key West Aquarium
4/5(380 reviews)
Come face to face with huge sharks, feed stingrays and learn about local tropical fish at this great aquarium.
Key West Shipwreck Museum
4/5(324 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.
Frequently asked questions
Photos of local treasures
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