Rockland Key Vacation Packages
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Top Rockland Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West
Price was CA $1,438, price is now CA $934 per person
CA $934
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
This place is amazing! The property is beautiful and quiet. The pool area was clean and well cared for. Our room was spacious, very clean and had everything we needed. The staff was kind and always helpful. We would definitely go back.
Reviewed on Feb 5, 2026
The Key West Hotel
Key West Historic District
Price was CA $6,662, price is now CA $4,080 per person
CA $4,080
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Everything was great. I couldn’t complain about anything if I wanted to. Thanks for a great stay!
Reviewed on Jan 28, 2026
The Perry Hotel & Marina Key West
Price was CA $2,479, price is now CA $1,697 per person
CA $1,697
per person
Mar 15 - Mar 20
found 3 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,151 reviews)
The Perry Hotel was a great experience. Traveled with a friend and stayed in a Mangrove room. Rooms were clean and well cared for. Pool and outside area is clean too. Although outside of downtown, there is a free shuttle that takes you downtown. If you are planning a specific time to go into town, you should ask if the shuttle is typically busy or not. It is first come first serve. Restaurants are great for breakfast or lunch when you arrive. It was a great quiet place to stay with the benefit of being on the water and being able to walk around the docks. Some excursions go out from the marinas as well.
Reviewed on Feb 1, 2026
Eden House
Key West Historic District
Price was CA $2,514, price is now CA $1,760 per person
CA $1,760
per person
Mar 15 - Mar 20
found 3 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (1,000 reviews)
The grounds were beautiful and well kept. The staff was excellent, room was super nice. Everything was so clean. The bike rentals were new. Great location!
Reviewed on Feb 5, 2026
Orchid Key Inn - Adults Only
Old Town Key West
Price was CA $3,211, price is now CA $2,273 per person
CA $2,273
per person
Mar 15 - Mar 20
found 3 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
Room was spotless. Beautiful bathroom. Very nice staff and amenities
Reviewed on Feb 2, 2026
Rockland Key Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
The price is CA $635 per night from Feb 8 to Feb 9
CA $635
CA $815 total
Feb 8 - Feb 9
includes taxes & fees
8.6/10 Excellent! (3,062 reviews)
The location was great. The room could have been cleaner. There were fruit flies in the bathroom.
Reviewed on Feb 6, 2026
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $388 per night from Feb 8 to Feb 9
CA $388
CA $473 total
Feb 8 - Feb 9
includes taxes & fees
8/10 Very Good! (2,066 reviews)
Everything was fantastic
Reviewed on Feb 1, 2026
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $437 per night from Feb 9 to Feb 10
CA $437
CA $576 total
Feb 9 - Feb 10
includes taxes & fees
8.8/10 Excellent! (1,801 reviews)
The room was very nice and homey feeling. The staff was very nice. We enjoyed breakfast lunch and diner at the restaurant the Waite staff was very friendly and food was good. We enjoyed the shuttle that is offered the drivers were knowledgeable about the island and history. Jeffery was the best. ...
Reviewed on Feb 3, 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.
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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.
