
Old Town Key West Vacation Packages
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Top Holiday Package Deals in Old Town Key West
Price found within the past 48 hours. Click for updated prices.

Ella's Cottages - Key West Historic Inns
Old Town Key West
Price was CA $2,773, price is now CA $1,795 per person
CA $1,795
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (366 reviews)
everything was easy and staff was very helpful!
Reviewed on Aug. 18, 2025

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Price was CA $2,671, price is now CA $1,809 per person
CA $1,809
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (775 reviews)
The property is cute with its own unique vibe. Our room did smell a bit musty, but it’s damp south Florida…so I took that with a grain of salt. There was some mold in our bathroom grout also, but I wasn’t in the mood to complain about something so petty. One thing I will rave about was Jefferson, he was working at the pool bar and not only was he a joy to talk to, he made a great drink!
Reviewed on Aug. 19, 2025


Ridley House - Key West Historic Inns
Key West Historic District
Price was CA $2,938, price is now CA $2,119 per person
CA $2,119
per person
Oct 28 - Nov 4
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (811 reviews)
Good breakfast wish it had more of a meat selection.....and climbing the stairs to the room was a little bit exhausting at times.
Reviewed on Aug. 20, 2025

Almond Tree Inn Hotel - Adults Only
Old Town Key West
Price was CA $3,983, price is now CA $2,904 per person
CA $2,904
per person
Oct 28 - Nov 4
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
10/10 Exceptional! (1,005 reviews)
Very nice place with great little touches and extremely friendly staff.
Reviewed on Aug. 21, 2025
Where to stay in Old Town Key West
Find the best Old Town Key West areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Key West

Key West Historic District
2 out of top 10 points of interest in this area
4.5/5(156 area reviews)
Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.
Old Town Key West Hotel Deals

Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Fully refundable
The price is CA $236 per night from Sep 7 to Sep 8
CA $236
CA $359 total
Sep 7 - Sep 8
includes taxes & fees
8.6/10 Excellent! (2,697 reviews)
Great location and fun vibe
"This resort has the perfect location, located at the southern most tip and end of Duval. Check in was easy and our room overlooked the Pineapple pool and bar, which made for fun evenings sitting on our balcony. The only downside to this resort was I felt the room was a little outdated and the bathroom ..."
Reviewed on Aug. 20, 2025

Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $307 per night from Sep 2 to Sep 3
CA $307
CA $429 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very Good! (304 reviews)
"The staff and service is exemplary. Ask for Nicole and Marsha at the Dorada beach bar. Both are awesome bartenders and great people!!!"
Reviewed on Aug. 19, 2025

The Reach Key West, Curio Collection by Hilton
1435 Simonton Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $312 per night from Sep 15 to Sep 16
CA $312
CA $434 total
Sep 15 - Sep 16
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Tropical paradise within your Reach
"Staff friendly and so accommodating! My wife somewhat particular about view from room; Phiwe and her colleague guided us to the perfect room overlooking pool and, a few feet beyond, the sandy beach. Lots of extras and you are able to walk over to sister property Casa Marina and hang out there too. ..."
Reviewed on Aug. 10, 2025
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.
Frequently asked questions
Discover the most popular places to visit in Old Town Key West

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

South Beach
The southernmost beach in the continental United States is a convenient sandy enclave, just minutes from the center of town.

Clarence S. Higgs Memorial Beach Park
Pay your respects at an impressive African burial site, explore landscaped gardens or snorkel with the family at this oceanfront beach park.
Things to do

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

MIAMI: Key West Day Trip with Boating Options
CA $136
per adult

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
CA $76
per adult
84% of travellers recommend
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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.