Key West Historic District Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Key West Historic District

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

President Hotel Villa

3.5 out of 5
South Beach
Price was CA $2,792, price is now CA $1,504 per person
CA $1,504
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very Good! (1,001 reviews)
the breakfast was good, and so was the service!

Reviewed on Apr 10, 2026

Fort Lauderdale Beach Resort by Vacatia

Fort Lauderdale Beach Resort by Vacatia

4 out of 5
East Fort Lauderdale
Price was CA $3,506, price is now CA $1,848 per person
CA $1,848
per person
Jun 25 - Jul 1
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.4/10 Very Good! (566 reviews)
Property close to all amenities

Reviewed on Apr 10, 2026

Miami Downtown Condos

Miami Downtown Condos

5 out of 5
Downtown Miami
Price was CA $3,306, price is now CA $1,748 per person
CA $1,748
per person
Jul 2 - Jul 7
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very Good! (135 reviews)
Excellent Location and unit. Host was very communicative and responsive once my arrival date approached. Just a few negatives, but some “minor” maintenance needs to be I wouldn’t list them here, they know what has to be done. done. Also, I would place a TV in the main area, if possible as I don’t really watch tv in bed. In addition, a great touch was having coffee and raw sugar was an added touch, as I do drink coffee and only use sugar in the raw! So 1000 extra points for me! Overall I would stay and recommend this location again.

Reviewed on Apr 5, 2026

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was CA $3,156, price is now CA $1,679 per person
CA $1,679
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.6/10 Excellent! (1,000 reviews)
Its my fourth time there and i loved it

Reviewed on Apr 6, 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was CA $2,820, price is now CA $1,505 per person
CA $1,505
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.4/10 Very Good! (2,145 reviews)
It was average No repeat for me

Reviewed on Apr 10, 2026

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
Old Town Key West

Old Town Key West

4 out of top 10 points of interest in this area
3.5/5(8 area reviews)

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 $444 per night from May 12 to May 13
CA $444
CA $600 total
May 12 - May 13
includes taxes & fees
8.8/10 Excellent! (3,205 reviews)
We stayed at the Dewey House and the room was great. The staff were fr

Reviewed on Apr 11, 2026

Southernmost Beach Resort and Guesthouses
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 $514 per night from May 10 to May 11
CA $514
CA $672 total
May 10 - May 11
includes taxes & fees
8.4/10 Very Good! (611 reviews)
We loved our stay! The room was small but the outside patio was a delight! The beach was beautiful with plenty of seating…. The staff was friendly, very helpful and informative! Planning on returning next year!!

Reviewed on Apr 11, 2026

Casa Marina Key West, Curio Collection by Hilton
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $646 per night from Apr 15 to Apr 16
CA $646
CA $820 total
Apr 15 - Apr 16
includes taxes & fees
9/10 Wonderful! (1,080 reviews)
Great ocean front view, the other rooms look at the parking lot so pay the extra money for ocean view. Resort fees are ridiculous so be prepared.

Reviewed on Apr 11, 2026

Pier House Resort & Spa
See all 1,687 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Key West Historic District vacation package cost?
Less than you might think — from a low CA $1,504, 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

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

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

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 $58
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
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
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

CA $75
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
See all activities in Key West

Explore a world of travel with Expedia

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