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.
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,645, price is now $916 per person
$916
per person
Jan 8 - Jan 13
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.
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,020, price is now $1,106 per person
$1,106
per person
Jan 8 - Jan 13
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. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $4,819, price is now $2,707 per person
$2,707
per person
Jan 15 - Jan 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

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,637, price is now $928 per person
$928
per person
Jan 9 - Jan 14
found 1 day 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.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,904, price is now $1,081 per person
$1,081
per person
Jan 8 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a garden, and luggage storage are also offered.

Top Historic Seaport hotels deals

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
$242 nightly
The price is $272 total per night
$272 total
Oct 27 - Oct 28
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
$229 nightly
The price is $258 total per night
$258 total
Oct 26 - Oct 27
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
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
$557 nightly
The price is $627 total per night
$627 total
Oct 27 - Oct 28
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
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
200 William Street, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$271 nightly
The price is $305 total per night
$305 total
Oct 26 - Oct 27
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
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
$259 nightly
The price is $292 total per night
$292 total
Nov 4 - Nov 5
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
Fitch Lodge - Key West Historic Inns

Fitch Lodge - Key West Historic Inns

3.5 out of 5
1030 Eaton St, Key West, FL
$192 nightly
The price is $216 total per night
$216 total
Oct 29 - Oct 30
Total with taxes and fees
An outdoor pool is featured at this hotel, along with free WiFi in public areas and luggage storage. Enjoy the free on-the-go breakfast each morning. Concierge services are provided for your convenience.
Pool
Breakfast included
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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.

Popular places to visit

Mallory Square which includes a sunset and a bay or harbor as well as a large group of people

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.

Mallory Square
Key West Aquarium showing marine life

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 Aquarium
Audubon House and Tropical Gardens showing a house

Audubon House and Tropical Gardens

4.5/5(291 reviews)

You can spend an afternoon exploring the galleries in Audubon House and Tropical Gardens in Key West. Discover the area's lively bars and its lively festivals.

Audubon House and Tropical Gardens

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 $916. 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

Mallory Square showing a sunset and general coastal views as well as a small group of people
Mallory Square featuring general coastal views, a sunset and sailing
St Maarten and St Martin
St Maarten and St Martin
Mallory Square as well as an individual male