Rockland Key Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Rockland Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Windward Pointe, Key West
The Key West Hotel
Hyatt Vacation Club at Beach House, Key West
The Gardens Hotel
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Ready to book your vacation to Rockland Key?

 

Choose your dates

Rockland Key Hotel Deals

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from May 26 to May 27
CA $220
CA $325 total
May 26 - May 27
includes taxes & fees
8.4/10 Very Good! (2,209 reviews)
All good

Reviewed on May 8, 2026

Blue Flamingo Resort Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
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! (1,810 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

Margaritaville Beach House Key West
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 $368 per night from May 25 to May 26
CA $368
CA $514 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (3,290 reviews)
Check in was a long line. Front desk gave me wrong information

Reviewed on May 7, 2026

Southernmost Beach Resort and Guesthouses
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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.