Historic Seaport Holidays from £2,393

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Your Historic Seaport Holiday

Take the fuss out of organising your next escape with a Historic Seaport holiday package. Immerse yourself in the sights and sounds of this wonderful neighbourhood and enjoy everything it has to offer. Your trip to Historic Seaport wouldn't be complete without seeing major attractions nearby such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Expedia will help you turn your ideal Historic Seaport holiday into reality, no matter your travel plans or budget.

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Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
£2,393
per person
30 Dec - 6 Jan
found 4 hours ago
Return direct flight included
London (LHR) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
When I checked in at the property, they offer me a upgrade for $75 for a ocean view that really lured me in because I wanted the best of the best I was spending time with a special person, but they didn’t tell me that it wasn’t a flat $75 upgrade which I found out later. It was $75 a night and they told me that utilities was $1000 which one their website said there was $300 paid at the hotel so they use my thousand dollars to pay for the $75 a night upgrade was wasn’t explained to me they made it seem like I was gonna get the thousand dollars back -$75 for the upgrade so they pretty much suckered me in to a upgrade deal that didn’t benefit me, but benefited the resort and when I made phone calls to acquired about it, I was told that it is what it is and if I reached out to management, they were gonna tell me the exact same thing was I didn’t appreciate it so I’m still trying to contact management, which is no contact number available and if you ask me personally, and I travel a lot, I would never recommend this hotel to anyone honestly goes a long way

Reviewed on 8 Oct 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
£2,989
per person
30 Dec - 6 Jan
found 4 hours ago
Return direct flight included
London (LHR) to Key West (EYW)
9.2/10 Wonderful! (563 reviews)
Property was everything as described, clean, in the heart of the excitement that is Key West Pool was refreshing and close to tiki bar and local entertainment. The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer

Reviewed on 6 Oct 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
Save 100% on your flight
£2,702
per person
30 Dec - 6 Jan
found 4 hours ago
Return direct flight included
London (LHR) to Key West (EYW)
9.2/10 Wonderful! (1,024 reviews)
Very nice room with lots of space. Comfortable bed. Nice pool area with an outdoor bar and live music/entertainment. Good food. Friendly, helpful staff. Great location next to the historic seaport and 3 blocks from Duval Street. Lots of shops, restaurants, and bars within easy walking distance. Would definitely stay here again.

Reviewed on 6 Oct 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
£2,572
per person
30 Dec - 6 Jan
found 4 hours ago
Return direct flight included
London (LHR) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

£2,703
per person
30 Dec - 6 Jan
found 4 hours ago
Return direct flight included
London (LHR) to Key West (EYW)
9.4/10 Exceptional! (3 reviews)
Key west is a vibe! My teenagers had a blast. No complaints. A lot of elders which is fine. I do have teens and they seems less than pleased while at he pool. We didn’t care though! We will be back, can not beat the location .

Reviewed on 26 Mar 2026

Where to stay in Historic Seaport

Find the best Historic Seaport areas and neighborhoods for the activities you enjoy most. Learn more about Historic Seaport
A white building with shutters, palm trees, and a lawn.

Old Town Key West

5 out of top 10 points of interest in this area

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Florida Keys Beaches.

A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

Downtown Key West

While visiting Downtown Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

A two-story house with green shutters and a wooden balcony.

Key West Historic District

2 out of top 10 points of interest in this area

Travellers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to stop by Duval Street and Florida Keys Beaches.

A marina with yachts docked, a prominent red building, and a coastal cityscape in the background.

New Town

While there might not be top attractions in New Town, you can explore the larger area and discover places like Smathers Beach and Fort East Martello Museum and Gallery.

A sunset over the ocean with scattered clouds.

Uptown - Upper Duval

If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.

Top hotels in Historic Seaport

Pier House Resort & Spa

Pier House Resort & Spa

1 Duval St Key West FL
Fully refundableReserve now, pay when you stay
£335
12 Oct - 13 Oct
includes taxes & fees
9/10 Wonderful! (1,351 reviews)
"Guest BEWARE, didn't think there would be a surcharge, but there was. A total of $262. and no one said anything. When we checked in and the asked for a credit card, I asked why, they said for unexpectedly occurred charges, nothing about surcharges. So PLEASE beware"

Reviewed on 7 Oct 2026

Pier House Resort & Spa
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

430 Duval St Key West FL
Fully refundableReserve now, pay when you stay
£212
11 Oct - 12 Oct
includes taxes & fees
9/10 Wonderful! (493 reviews)
"A beautiful hotel, but we found the staff lacking. We arrived early and were told we would receive an update when we could check in. We went back after check in time and they forgot to give us our breakfast credit. We also prepaid for breakfast as part of our reservation but it was for a limited ..."

Reviewed on 8 Oct 2026

La Concha Key West, Autograph Collection
Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

Zero Duval St. Key West FL
£328
26 Oct - 27 Oct
includes taxes & fees
Ocean Key Resort - A Noble House Resort
See all 2,689 properties in Historic Seaport
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.

Frequently asked questions

How much does a Historic Seaport travel package cost?
We make it easy for everyone to travel, with Historic Seaport travel packages starting from as little as £2,393. You'll have the flexibility to bundle your favourite airlines, hotels and car rental. For the ultimate getaway, why not add a couple of activities and tours to your itinerary?
If I'm not able to travel, can I cancel my Historic Seaport travel package?
If your holiday plans in Historic Seaport have been upended, it's a relief to know that it's possible to amend or cancel your booking. If you made your booking less than 24 hours ago, you may be eligible to receive a refund. If your booking is older than that, your airline, hotel or car rental company may impose a fee. To find out more, visit our Customer Service Portal.
How do I get a cheap travel package to Historic Seaport?
Creating your own Historic Seaport travel package with Expedia is the easiest way to save. We have more than 550 air carriers and 1,000,000 hotel options globally. With such a huge range to pick from, you'll have no difficulty putting together your dream holiday.
Does Expedia offer Book Now, Pay Later Historic Seaport holidays?
Expedia has partnered with online lender Klarna to make your next getaway easier on the purse strings. Paying by instalment means you can spread the costs of your next dream escape, leaving you with more money to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that suits your budget. Take a look at these flexible payment options:
  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If paying a little each month sounds right for you, choose this option at checkout.
  • Pay in instalments holidays: If you'd prefer to pay for your escape in multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to hit that "book now" button, go for a low deposit holiday payment plan from Klarna.
Where should I stay in Historic Seaport?
Most who travel to Historic Seaport put both Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens on their sightseeing itineraries. Why not consider a hotel close to one of these iconic attractions?
What are the top hotels in Historic Seaport?
If it's your first time in Historic Seaport, reserve a room at The Gates Hotel Key West or Crowne Plaza Key West-La Concha. Both hotels have good amenities and are favourites with lots of travellers.
How far in advance should I book my Historic Seaport holiday?
While not all air carriers release ticket prices early, customers are usually able to compare international fares on Expedia up to 12 months in advance. This is the time you can nab some incredible deals. If you're booking late, you could still be in luck. Sometimes the lowest prices emerge a few weeks prior to departure.
What does an Expedia Historic Seaport travel package include?
Packages include hotels, flights and rental cars, but you can combine any of them to create your dream Historic Seaport holiday. You can also add on some activities and experiences once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll get access to deals you won't find anywhere else.
What should I know before booking a Historic Seaport travel package?
When you book your hotels, flights and car rentals together, you'll pick up incredible discounts. Whether you're organising a beach escape in a villa or prefer to stay in an upscale city hotel, Expedia can make it happen for less.
Can I choose my airline with a Historic Seaport Expedia travel package?
Yes, you can. Expedia has access to more than 550 airline partners worldwide, so select the carrier that's a good fit for your budget needs.

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
A historic building with a tall tower, palm trees, and a vintage trolley.

Key West Shipwreck Museum

8.6/10 (361 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.
See properties
A two-story house with green shutters and a wooden balcony.

Audubon House and Tropical Gardens

8.8/10 (378 reviews)
Visit a house named after famed naturalist John James Audubon. Learn the history of why the house came to be here.
See properties
A large cruise ship docked at a pier with palm trees and a clear sky.

Mallory Dock

8.8/10 (1,152 reviews)
You can find the perfect gifts to bring home at Mallory Dock during your trip to Key West. Wander the area's seaside or simply enjoy one of its lively bars.
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Key West Historic Seaport

Find out about the history of Key West when you take a trip to Key West Historic Seaport. Discover the area's lively bars and its entertainment choices.
See properties

Sails To Rails Museum at Flagler Station

You can spend time exploring the galleries in Sails To Rails Museum at Flagler Station in Key West. Stroll along the beautiful beaches or seek out the cycling trails.
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Red Barn Theater

8.0/10 (10 reviews)
You can get tickets for a performance at Red Barn Theater on your trip to Key West. Wander the seaside and beautiful beaches in the area.
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Donkey Milk House

7.4/10 (6 reviews)
You can spend an afternoon studying the exhibits at Donkey Milk House during your travels in Key West. Discover the area's beautiful sunsets or seek out its cycling trails.
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Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

£32
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

£25
per adult
82% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
 Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

£41
per adult
86% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
See all activities in Key West

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.