Key West Historic District Vacation Packages

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Top Holiday Package Deals in Key West Historic District

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

Creekside Inn

2.5 out of 5
Price was CA $2,785, price is now CA $1,261 per person
CA $1,261
per person
May 16 - May 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
Room was small but clean.

Reviewed on Feb 26, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $10,338, price is now CA $4,141 per person
CA $4,141
per person
May 4 - May 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
5.8/10 (311 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was CA $5,416, price is now CA $3,036 per person
CA $3,036
per person
May 13 - May 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
My boyfriend and I had such an incredible, relaxing stay. Everyone was very nice but our front desk gentleman, Chris, really stood out. The pool was clean and the sun hit there most of the day. The bar was fun and the live music was very enjoyable. Thank you Key West Hotel. 10/10 recommend.

Reviewed on Feb 20, 2026

President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was CA $2,420, price is now CA $1,388 per person
CA $1,388
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (997 reviews)
nice location, good room. nice breakfast and evening reception

Reviewed on Feb 22, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was CA $17,385, price is now CA $10,275 per person
CA $10,275
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very Good! (1 review)

Where to stay in Key West Historic District

Find the best Key West Historic District areas and neighborhoods for the activities you enjoy most. Learn more about Key West Historic District
Key West Historic District

Old Town Key West

4 out of top 10 points of interest in this area

Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.

Find hotels in Old Town Key West

Key West Historic District Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
The price is CA $583 per night from Mar 12 to Mar 13
CA $583
CA $756 total
Mar 12 - Mar 13
includes taxes & fees
8.8/10 Excellent! (3,112 reviews)
Too many children!! No repeat rewards!!

Reviewed on Feb 26, 2026

Southernmost Beach Resort and Guesthouses
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
601 Front St Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $609 per night from Mar 22 to Mar 23
CA $609
CA $780 total
Mar 22 - Mar 23
includes taxes & fees
9/10 Wonderful! (1,013 reviews)
Excellent location, clean and luxurious room. Restaurant on premises was amazing.

Reviewed on Feb 24, 2026

Hyatt Centric Key West Resort and Spa
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $912 per night from Mar 4 to Mar 5
CA $912
CA $1,119 total
Mar 4 - Mar 5
includes taxes & fees
8.4/10 Very Good! (556 reviews)
All was great staff, room cleanliness. But one thing we were very disappointed in was the fact that one of our beach days we did not have a beach chair!! So disappointing for the price we pay that you don’t have enough beach chairs and we had to sit on the ground.

Reviewed on Feb 25, 2026

Casa Marina Key West, Curio Collection by Hilton
See all 1,702 properties in Key West Historic District
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.
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Frequently asked questions

How much does a Key West Historic District vacation package cost?
Less than you might think — from a low CA $1,261, actually! By combining flights, hotels and car rentals into a custom-built vacation package, your Key West Historic District escape is just a few clicks away.
How do I get a cheap travel package to Key West Historic District?
Book everything in the one place with our Key West Historic District vacation packages. We have deals on flights, hotels, tours and more that'll keep your pocketbook happy and adventurous side satisfied. And, with more than 550 airlines and 1,000,000 hotel options throughout the world to choose from, you'll have the flexibility to mix and match as you want.
Where should I stay in Key West Historic District?
Travelers come from far and wide to experience Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens in Key West Historic District. Book yourself a room within a stone's throw of these must-see attractions to make sightseeing easy.
What are the top hotels in Key West Historic District?
Secure a room at Southernmost Retreat: 2 Blocks From Duval In Old Town. It's one of the area's most sought-after hotels. Another top option in Key West Historic District is Walk to Duval Waterfront Marina View 2-Bed Galleon + Beach + Sunset Tiki Bar.
How far in advance should I book my Key West Historic District vacation?
Savvy travelers book early. Air carriers typically release flights up to 12 months ahead of departure, and this is an excellent opportunity to pick up some of the lowest prices. Just been told you need to take some vacation time next week? Don't fret. Expedia are never short of fantastic deals to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Key West Historic District travel package include?
Hotels, flights and a cool set of wheels for your road trip adventures. Simply select your preferred bundle and get access to incredible deals. Once you've made your booking, add on a few sightseeing tours and watch your savings stack up. When it comes to creating your Key West Historic District break, you're in control!
What should I know before booking a Key West Historic District travel package?
You'll enjoy amazing savings when you combine your flights, hotels and rental cars into a travel package. Plus, booking everything together will make your trip planning easier. So why waste time or money? Whether you're putting together a ritzy romantic getaway or a budget solo adventure, check out our vacation packages today.
Can I choose my airline with a Key West Historic District Expedia vacation package?
Yes, and with more than 550 airlines to select from across the globe, you have loads of choice. Look through the available options and see which airline suits your needs and budget.
If I'm not able to travel, can I cancel my Key West Historic District vacation package?
If your vacation plans in Key West Historic District have changed, it's a relief to know that it's possible to cancel your booking. If your booking was made less than 24 hours ago, you may be eligible for a refund. If your booking is older than that, your hotel, airline or car rental company may charge fees. To learn more, check our Customer Service Portal.

Discover the most popular places to visit in Key West Historic District

Duval Street featuring signage

Duval Street

Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.

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

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.

Mallory Square
Harry S. Truman Little White House showing a house

Harry S. Truman Little White House

Visit the winter home of President Harry S. Truman to see where some of America’s most important post-war decisions were made.

Harry S. Truman Little White House

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $61
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Friends cheers with cocktails on Key West cruise

Key West Afternoon At The Reef Snorkeling Adventure with Open Bar!

CA $65
per adult
92% of travellers recommend
Key West Afternoon At The Reef Snorkeling Adventure with Open Bar!
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $79
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
See all activities in Key West

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.