Key West Historic District Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

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

    Find the right fit

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

    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.
Embassy Suites by Hilton Deerfield Beach Resort & Spa

Embassy Suites by Hilton Deerfield Beach Resort & Spa

3.5 out of 5
per person
Sep 28 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.4/10 Very Good! (1,034 reviews)
No hairdryer in rooms was something we weren't a big fan of

Reviewed on Aug. 12, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Sep 11 - Sep 16
found 7 hours ago
Roundtrip flight included
Toronto (YTZ) to Miami (MIA)
8/10 Very Good! (1 review)
Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
per person
Sep 28 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (2,473 reviews)
The location is great and the customer service was excellent

Reviewed on Aug. 12, 2025

Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
per person
Oct 5 - Oct 12
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (149 reviews)
We had a great time at the hotel and were impressed with the well-maintained and spacious rooms. The mix of renters, vacationers, and pets on-site created a lively and diverse atmosphere, with everyone being friendly and welcoming. However, there was one issue that I would like to bring to your attention. Some previous tenants or vacationers had let their pets urinate in the common areas, which was unpleasant. Additionally, we noticed a smell in our room’s living room carpet, which was a result of pet urine. As pet owners, we understand the strong odor of pet urine and appreciate it when guests take responsibility for cleaning up after their pets. I hope this feedback helps improve the experience for future guests.

Reviewed on Aug. 4, 2025

Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (270 reviews)
Great location, friendly staff and good service.

Reviewed on Aug. 11, 2025

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
Default Image

Old Town Key West

3 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 $244 per night from Aug 26 to Aug 27
CA $244
CA $367 total
Aug 26 - Aug 27
includes taxes & fees
8.6/10 Excellent! (2,672 reviews)
"Pools are always packed with no chairs avaliable after 10am. Beach is a mud playground. Rooms are clean, staff is nice. I was supposed to get a free bottle of wine and 30usd boucher but I didn't bring it up to their attention I wouldn't have gotten it. Parking is $46 per night plus a amenity fee ..."

Reviewed on Aug. 11, 2025

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 $327 per night from Aug 25 to Aug 26
CA $327
CA $457 total
Aug 25 - Aug 26
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Great food. Comfortable room. Friendly staff"

Reviewed on Aug. 9, 2025

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 $304 per night from Sep 2 to Sep 3
CA $304
CA $425 total
Sep 2 - Sep 3
includes taxes & fees
8.4/10 Very Good! (287 reviews)
"Loved this place."

Reviewed on Aug. 9, 2025

Casa Marina Key West, Curio Collection by Hilton
See all 1,753 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 $716, 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
Southernmost Point

Southernmost Point

Snap a memorable photograph from the edge of North America at this monumental landmark.

Southernmost Point
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

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $55
per adult
92% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar

Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar

CA $136
per adult
74% of travellers recommend
Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar
MIAMI: Key West Day Trip with Boating Options

MIAMI: Key West Day Trip with Boating Options

CA $121
per adult
MIAMI: Key West Day Trip with Boating Options
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.