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.
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
The beach was beautiful

Reviewed on Jul. 11, 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 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8/10 Very Good! (1 review)
The Shelborne By Proper

The Shelborne By Proper

4 out of 5
South Beach
Save 100% on your flight
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9.6/10 Exceptional! (4 reviews)
Wonderful hotel. Beautiful design and very attentive staff.

Reviewed on Jul. 7, 2025

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Perfectly located on Ocean Drive with an old-school Art Deco vibe that feels both historic and fresh. The room was spotless, the A/C was ice cold, and the bed was genuinely comfortable. Staff was friendly and helpful. You’re across from the beach, but it still feels like a quiet escape. Would absolutely stay here again.

Reviewed on Jul. 1, 2025

President Hotel

President Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.4/10 Very Good! (1,596 reviews)
It was good, the one who attended us at check in was quite friendly and at breakfast anyway everything was good, very kind... I didn't like it was that we tried to get a glass of hot water and although it was only a "question" she replied "right now I'm very busy, come back in 10 minutes". On the day of cleaning, the one who was going to clean looked at me super badly "I knew that we can't be in the room when they go to do cleaning" but she was not nice at all and we were just about to leave the room...

Reviewed on Jul. 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
Key West Historic District

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 $272 per night from Aug 4 to Aug 5
CA $272
CA $398 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (2,611 reviews)
"Love this property; property is bigger than I thought but had so much to offer; had fun activities if you wanted to be involved; a block from southern most point; everything is so close to stay"

Reviewed on Jul. 9, 2025

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 $296 per night from Aug 5 to Aug 6
CA $296
CA $414 total
Aug 5 - Aug 6
includes taxes & fees
8.2/10 Very Good! (224 reviews)
"Is very clean, the room is nice"

Reviewed on Jul. 11, 2025

Casa Marina Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton
4 out of 5
1435 Simonton Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from Jul 18 to Jul 19
CA $251
CA $364 total
Jul 18 - Jul 19
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
"Beach access was great! Rooms very clean and all staff was friendly and helpful. Be prepared for the $50/day valet charge and no self parking available. We were SO glad we stayed here versus the nearby Southernmost resort. Beach seaweed was cleaned up and maintained. The beach at Southernmost was ..."

Reviewed on Jul. 6, 2025

The Reach Key West, Curio Collection by Hilton
See all 1,760 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 $664, 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

4.5/5(161 reviews)

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

4/5(160 reviews)

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

Southernmost Point
Mallory Square

Mallory Square

4.5/5(148 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.

Mallory Square

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $69
per adult
92% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
MIAMI: Key West Day Trip with Boating Options

MIAMI: Key West Day Trip with Boating Options

CA $106
per adult
MIAMI: Key West Day Trip with Boating Options
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
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.