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
per person
Oct 19 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
Wonderful place for a weekend

Reviewed on Jul. 28, 2025

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
per person
Oct 19 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
5.8/10 (303 reviews)
It was great for beach access. Nothing in our room worked. Coffee pot was broke. Stove was broke. We had to switch on and off the breakers to use it. Toilet would tflush half the time.

Reviewed on Jun. 21, 2025

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.6/10 Exceptional! (5 reviews)
Quiet.Lobby was nice and smelled amazing. Staff was good. Loved the gym/studio. Dislikes: No hot water in the shower. Lobby smelled amazing but wasn’t consistent throughout the building.

Reviewed on Jul. 17, 2025

Aloha Fridays

Aloha Fridays

3 out of 5
South Beach
per person
Oct 10 - Oct 15
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8.4/10 Very Good! (36 reviews)
Friendly and kind staff. (that was the highlight) Nice room. Great location.

Reviewed on Jul. 26, 2025

Pier Sixty-Six (Pier 66)

Pier Sixty-Six (Pier 66)

5 out of 5
East Fort Lauderdale
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.6/10 Exceptional! (99 reviews)
The resort is newly renovated and reopened in March of this year. Everything is beautiful!!! The service is top notch.

Reviewed on Jul. 28, 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
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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 $252 per night from Aug 28 to Aug 29
CA $252
CA $377 total
Aug 28 - Aug 29
includes taxes & fees
8.6/10 Excellent! (2,650 reviews)
"Stay was good but we expected the private beach and it was not clean due to seaweeds so we couldn't use at all. The only reason we booked that hotel due to private beach access which was not available. Otberwise everything was good."

Reviewed on Jul. 27, 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 $293 per night from Aug 13 to Aug 14
CA $293
CA $412 total
Aug 13 - Aug 14
includes taxes & fees
8.2/10 Very Good! (255 reviews)
"Private beach was great"

Reviewed on Jul. 27, 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 $333 per night from Aug 24 to Aug 25
CA $333
CA $457 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (1,021 reviews)
"Everything was excellent. One thing is just the elevator next to the pool was not working for 3 days, but other than that no complains. Staff was very nice."

Reviewed on Jul. 26, 2025

The Reach Key West, Curio Collection by Hilton
See all 1,749 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 $886, 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 $62
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 $135
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 $105
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.