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.
Hyatt Vacation Club at Beach House, Key West
Price was CA $1,747, price is now CA $1,289 per person
CA $1,289
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.4/10 Exceptional! (1,017 reviews)
Wry clean and updated property. The screened in porch was a plus. Clean grounds with small beach access. Nice location to key west if you have a car.
Reviewed on Apr 17, 2026
The Key West Hotel
Key West Historic District
Price was CA $1,982, price is now CA $1,394 per person
CA $1,394
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (542 reviews)
Great location! We were very impressed with Chris! He told us where to park and was very welcoming when we arrived. The loft room setup was perfect for us and the Bali Bar did not disappoint! We will be back!!
Reviewed on Apr 5, 2026
The Gardens Hotel
Old Town Key West
Price was CA $2,608, price is now CA $1,911 per person
CA $1,911
per person
Jun 28 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.8/10 Exceptional! (1,002 reviews)
Breakfasts were great and they had a very good selection of drinks at the bar.
Reviewed on Apr 9, 2026
Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
Price was CA $4,571, price is now CA $3,370 per person
CA $3,370
per person
Jul 2 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (354 reviews)
Location was great. Near most of Key West Attractions. Parked the car and walked everywhere.
Reviewed on Apr 14, 2026
Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Price was CA $2,918, price is now CA $2,180 per person
CA $2,180
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.4/10 Very Good! (614 reviews)
We had a great time. The hotel is beautiful and in a great location. The beach and two pools are perfectly located. A easy walk to Duval st. The rooms are nice but not much storage or closet space for clothing. The showers could use some shelving for personal shower products. The food and drinks are outrageously expensive, so you may wa t to think about dinner and drinks elsewhere. Overall we really loved the place. The staff was amazing. We will come back next year.
Reviewed on Apr 11, 2026
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(157 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 refundableReserve now, pay when you stay
The price is CA $363 per night from May 19 to May 20
CA $363
CA $509 total
May 19 - May 20
includes taxes & fees
8.8/10 Excellent! (3,220 reviews)
Very nice property, great location, right near the beach(which is rare in Key West). Our only issue was the housekeeping services. We took the privacy sign off the door and were expecting to get the room cleaned while we were gone for the whole morning. Usually, thats when the cleaning is done. We ...
Reviewed on Apr 19, 2026
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 $443 per night from May 3 to May 4
CA $443
CA $590 total
May 3 - May 4
includes taxes & fees
8.4/10 Very Good! (616 reviews)
No beach view and we had an additional unexpected charge of $60 plus taxes
Reviewed on Apr 19, 2026
Opal Key Resort & Marina, Key West
245 Front Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $368 per night from May 3 to May 4
CA $368
CA $468 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (1,078 reviews)
We love our stay and staff was awesome! Can’t wait for our next visit back!
Reviewed on Apr 19, 2026
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
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
CA $58
per adult
94% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $79
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
CA $75
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.