Historic Seaport Vacation Packages 2025/2026 from $838

Historic Seaport flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Ridley House - Key West Historic Inns

Key West Historic District

Save 100% on your flight

$838

per person

Dec 5 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to Key West (EYW)

An outdoor pool is featured at this hotel, along with free WiFi in public areas and luggage storage. Enjoy the free buffet breakfast each morning. Concierge services are provided for your convenience.

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$974

per person

Nov 18 - Nov 24

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) 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

Old Town Key West

Save 100% on your flight

$990

per person

Nov 7 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) 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.

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$1,045

per person

Nov 7 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to Key West (EYW)

This hotel features an outdoor pool and a poolside bar. 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.

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$1,031

per person

Nov 7 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) 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

Pier House Resort & Spa

1 Duval St, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$387 nightly

$435 total

Sep 28 - Sep 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.

On private beach

Pool

La Concha Key West, Autograph Collection

430 Duval St, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$208 nightly

$234 total

Oct 13 - Oct 14

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

Hyatt Centric Key West Resort and Spa

601 Front St, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$253 nightly

$285 total

Sep 28 - Sep 29

Total with taxes and fees

This eco-certified 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

The Marker Key West Harbor Resort

200 William Street, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$226 nightly

$254 total

Oct 14 - Oct 15

Total with taxes and fees

This eco-certified 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

Fitch Lodge - Key West Historic Inns

1030 Eaton St, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$141 nightly

$159 total

Oct 7 - Oct 8

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

NYAH Key West - Adults Only

420 Margaret Street, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$113 nightly

$128 total

Sep 29 - Sep 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.

Pool

Hot Tub

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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

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.

Audubon House and Tropical Gardens

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.

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 $838. 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.