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.
Kona Kai Oasis

Kona Kai Oasis

3 out of 5
Old Town Key West
Price was $1,553, price is now $1,090 per person
$1,090
per person
Dec 14 - Dec 18
found 8 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
An outdoor pool, free self parking, and concierge services are featured at this guesthouse. WiFi in public areas is free. A garden, a picnic area, and luggage storage are also on offer.
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was $2,939, price is now $2,006 per person
$2,006
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Old Town Key West
Price was $2,272, price is now $1,564 per person
$1,564
per person
Dec 14 - Dec 18
found 8 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
A private beach and an outdoor pool are featured at this smoke-free resort. Enjoy the hot tub and perks like free self parking and free WiFi. A computer station, dry cleaning, and luggage storage are also on offer.
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Price was $3,291, price is now $2,311 per person
$2,311
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Price was $1,790, price is now $1,260 per person
$1,260
per person
Dec 14 - Dec 18
found 8 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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 WiFi. Self parking, concierge services, and barbecue grills are also on offer.

Top Historic Seaport hotels deals

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
$237 nightly
The price is $267 total per night
$267 total
Nov 29 - Nov 30
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
$401 nightly
The price is $451 total per night
$451 total
Nov 22 - Nov 23
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
$298 nightly
The price is $335 total per night
$335 total
Nov 16 - Nov 17
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
$326 nightly
The price is $367 total per night
$367 total
Nov 22 - Nov 23
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

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
$317 nightly
The price is $357 total per night
$357 total
Dec 1 - Dec 2
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
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
511 Caroline St Key West FL
$315 nightly
The price is $354 total per night
$354 total
Nov 12 - Nov 13
Total with taxes and fees
This guesthouse features an outdoor pool and a bar/lounge. WiFi in public areas is free. You'll appreciate the area shuttle, business center, and coffee shop/cafe.
Pool
Pet friendly
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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 $1,090. 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.