Rockland Key Vacations from $574
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The Latest Rockland Key Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Ibis Bay Beach Resort
Sep 25 - Sep 28Ibis Bay Beach Resort + Flight
Northside Resort3 nights2.5 star property8.2/10 - Very Good (2,284 reviews)Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop$818$574found 1 day agoper traveler - The Key West Hotel
Sep 25 - Sep 28The Key West Hotel + Flight
Key West Historic District3 nights3.0 star property9.2/10 - Wonderful (559 reviews)"We loved staying here and highly recommended it. Only thing that people might not like is the solo musicians play till 11pm every night. We didn’t mind it since we are not early birds."Reviewed June 7, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop - Coconut Beach Resort
Sep 25 - Sep 28Coconut Beach Resort + Flight
Old Town Key West3 nights2.5 star property8.8/10 - Excellent (208 reviews)"So overall its a nice spot but the units are split with a dividing door, so when we arrived to check out the room the doors were not locked and people were in our unit. For it being an ocean view with a premium price, the resort description said they have someone who frequently cleans the beach access from debris but it was completely covered in sargasim seaweed with no access to the water. Make sure you check the sargasim season because it very much limits your access to the beach. On our..."Reviewed July 15, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop - Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Oct 3 - Oct 8Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub! + Flight
Old Town Key West5 nights3.0 star property10/10 - Exceptional (6 reviews)"Although not on the beach you are a ten min bike ride from most. All restaurants Duval has to offer. The house is cute, clean and the back yard is awesome. We will stay again nextime!"Reviewed November 24, 2025Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop$2,203$1,647found 1 day agoper traveler - Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Oct 8 - Oct 14Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool! + Flight
Old Town Key West6 nights3.5 star property8.8/10 - Excellent (3 reviews)"The location to the things we wanted to do was perfect"Reviewed May 1, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop
Rockland Key Hotel Deals
Margaritaville Beach House Key West
Margaritaville Beach House Key West4.0 star property
6.6 mi from Rockland Key
8.8 out of 10, Excellent, (1,800 reviews)
8.8/10
Excellent
(1,800 reviews)
"Had to switch rooms after day 2 afternoon. Never got room cleaned on day 4… could have been better, but most staff was very helpful and polite."
$238 nightly
The price is $268
$268 total
Aug 11 - Aug 12
Total with taxes and fees
8.2 out of 10, Very Good, (1,000 reviews)
8.2/10
Very Good
(1,000 reviews)
"Very spacious room, there's no breakfast but coffe or tea offer in the near tiki bar
There also a restaurant "
$119 nightly
The price is $134
$134 total
Jul 19 - Jul 20
Total with taxes and fees
7.6 out of 10, Good, (1,000 reviews)
7.6/10
Good
(1,000 reviews)
"No era suficiente el aire acondicionado el lavamanos estaba tupido"
$156 nightly
The price is $175
$175 total
Jul 19 - Jul 20
Total with taxes and fees
9.0 out of 10, Wonderful, (1,000 reviews)
9.0/10
Wonderful
(1,000 reviews)
"We happened upon this quaint resort on a weekend to the Keys. What a great spot! It is not on one of the main keys but is close to Key West and other fun locations. The resort had hammocks to relax in, a pool, docks, outdoor activities and a small breakfast (don't plan on filling up on it if you are hungry though). Room was quiet even though it was right next to the pool and there are so many different options there! We would definitely stay there again! Beds were comfortable and the bathroom...
$168 nightly
The price is $189
$189 total
Aug 10 - Aug 11
Total with taxes and fees
Casa Marina Key West, Curio Collection by Hilton
Casa Marina Key West, Curio Collection by Hilton4.0 star property
Casa Marina, 7.8 mi from Rockland Key
8.4 out of 10, Very Good, (765 reviews)
8.4/10
Very Good
(765 reviews)
"I really enjoyed my stay. The staff went out of their way to make you feel welcome and cared for. I want to make special mention of Ann - Marie at the front desk, Robert in the breakfast dining area, and Gabor from in he breakfast dining area, who went out of their way to make sure my stay was comfortable and catered to. I would definitely recommend this stay to others."
$279 nightly
The price is $314
$314 total
Aug 11 - Aug 12
Total with taxes and fees
Parrot Key Hotel & Villas
Parrot Key Hotel & Villas4.0 star property
Northside Resort, 6.4 mi from Rockland Key
9.0 out of 10, Wonderful, (1,421 reviews)
9.0/10
Wonderful
(1,421 reviews)
$206 nightly
The price is $232
$232 total
Aug 10 - Aug 11
Total with taxes and fees
8.6 out of 10, Excellent, (2,346 reviews)
8.6/10
Excellent
(2,346 reviews)
$213 nightly
The price is $240
$240 total
Aug 16 - Aug 17
Total with taxes and fees
Hyatt Centric Key West Resort and Spa
Hyatt Centric Key West Resort and Spa4.0 star property
Historic Seaport, 8.3 mi from Rockland Key
9.0 out of 10, Wonderful, (1,017 reviews)
9.0/10
Wonderful
(1,017 reviews)
"Highly recommend the Hyatt Centric. Perfect location to walk easily to the most popular tourist attractions, restaurants, and view the beautiful sunset. Staff was friendly, great amenities, beautiful resort, and large, clean rooms."
$261 nightly
The price is $294
$294 total
Aug 11 - Aug 12
Total with taxes and fees
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.