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 Windward Pointe, Key West
Price was CA $2,226, price is now CA $1,562 per person
CA $1,562
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,066 reviews)
The hidden resort fees were absolutely ridiculous! $40 a day, plus $5 a day plus $150 coverage without any explanation. This property is located directly next to the airport and they do not provide a shuttle service to pick you up. We used Uber for everything, another extra expense. ( The Hampton Inn next door had a shuttle that went everywhere)
Reviewed on May 5, 2026
The Key West Hotel
Key West Historic District
Price was CA $3,179, price is now CA $2,290 per person
CA $2,290
per person
Jun 27 - Jul 2
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (552 reviews)
The staff at the hotel were excellent. Very friendly and helpful. Room was very clean and comfortable. We were right in the middle of the old district which had many many places to explore. Hotel had a wonderful hidden pool with live music/bar next to it in case we just wanted to relax after exploring all day.
Reviewed on Apr 21, 2026
Hyatt Vacation Club at Beach House, Key West
Price was CA $2,997, price is now CA $2,216 per person
CA $2,216
per person
Jun 27 - Jul 2
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,034 reviews)
Nice to have laundry in the apartment
Reviewed on May 7, 2026
The Gardens Hotel
Old Town Key West
Price was CA $2,711, price is now CA $2,108 per person
CA $2,108
per person
Jun 27 - Jul 2
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.8/10 Exceptional! (1,003 reviews)
This was one of the nicest places we have ever stayed. It felt like a tropical oasis but was only a block over from Duval. Wine tasting room was great and the hotel cat, Lucy, was the sweetest! Breakfast each morning was amazing! We would definitely stay here again when we come back to visit!
Reviewed on Apr 26, 2026
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Old Town Key West
Price was CA $4,925, price is now CA $3,888 per person
CA $3,888
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
10/10 Exceptional! (1 review)
Loved the closeness to Duval st and the privacy
Reviewed on Oct 17, 2025
Rockland Key Hotel Deals
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from May 27 to May 28
CA $220
CA $325 total
May 27 - May 28
includes taxes & fees
8.4/10 Very Good! (2,210 reviews)
This is a very cool resort!Main Lobby & Reception area is super stylish & inviting! I didn't stay in the more modern tower, I was over in what they call the Garden Hotel (probably the original 2 story unit). The rooms were very clean/comfortable. I loved the styling! There are several light accents ...
Reviewed on May 9, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $267 per night from Jun 8 to Jun 9
CA $267
CA $386 total
Jun 8 - Jun 9
includes taxes & fees
8.8/10 Excellent! (1,812 reviews)
Staff was very helpful with all our needs. I would only recommend that the hot tub had hot water. It was cold and the jets were weak. Otherwise it was a perfect spot for us. We will be back.
Reviewed on May 7, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
The price is CA $358 per night from Jun 2 to Jun 3
CA $358
CA $503 total
Jun 2 - Jun 3
includes taxes & fees
8.8/10 Excellent! (3,291 reviews)
Check in was a long line. Front desk gave me wrong information
Reviewed on May 7, 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.
