Rockland Key Vacations from $639
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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 10 - Sep 14Ibis Bay Beach Resort + Flight
Northside Resort4 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$883$639found 1 day agoper traveler - Coconut Beach Resort
Sep 18 - Sep 24Coconut Beach Resort + Flight
Old Town Key West6 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 - The Key West Hotel
Sep 1 - Sep 6The Key West Hotel + Flight
Key West Historic District5 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 - MIA • Nonstop MIA - BOS • Nonstop - The Gardens Hotel
Sep 18 - Sep 24The Gardens Hotel + Flight
Old Town Key West6 nights4.0 star property9.8/10 - Exceptional (1,000 reviews)"Loved the hotel, Super cozy and private …"Reviewed July 3, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop - Lighthouse Hotel - Key West Historic Inns
Sep 10 - Sep 14Lighthouse Hotel - Key West Historic Inns + Flight
Old Town Key West4 nights3.5 star property9.0/10 - Wonderful (960 reviews)"Lovely property, very lush and private. Yet close to everything especially the lighthouse and the Hemmingway house. Plenty to do lots of great bars and restaurants."Reviewed July 16, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop$933$679found 1 day agoper traveler
Rockland Key Hotel Deals
9.0 out of 10, Wonderful, (1,439 reviews)
9.0/10
Wonderful
(1,439 reviews)
$178 nightly
The price is $200
$200 total
Aug 11 - Aug 12
Total with taxes and fees
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Fairfield by Marriott Inn & Suites Key West at The Keys Collection3.5 star property
New Town, 5.1 mi from Rockland Key
8.6 out of 10, Excellent, (1,050 reviews)
8.6/10
Excellent
(1,050 reviews)
"The staff was so helpful"
$177 nightly
The price is $199
$199 total
Aug 3 - Aug 4
Total with taxes and fees
Hilton Key West Resort & Marina
Hilton Key West Resort & Marina4.0 star property
Stock Island, 3.9 mi from Rockland Key
9.0 out of 10, Wonderful, (1,848 reviews)
9.0/10
Wonderful
(1,848 reviews)
"Beautiful property, restaurant was great, only thing to be aware of is that the location is really not that close to anything so you are limited to the shuttle provided by hotel to downtown Key West or utilize uber/lyft.
Also, we did not take advantage of the free rental for kayak or paddle boarding as the water was very brown and smelled."
$191 nightly
The price is $214
$214 total
Aug 2 - Aug 3
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key West4.0 star property
5.2 mi from Rockland Key
8.4 out of 10, Very Good, (1,048 reviews)
8.4/10
Very Good
(1,048 reviews)
$165 nightly
The price is $186
$186 total
Aug 9 - Aug 10
Total with taxes and fees
Hilton Garden Inn Key West / The Keys Collection
Hilton Garden Inn Key West / The Keys Collection3.5 star property
New Town, 5.1 mi from Rockland Key
8.0 out of 10, Very Good, (1,276 reviews)
8.0/10
Very Good
(1,276 reviews)
"Great place to stay for a weekend"
$155 nightly
The price is $174
$174 total
Aug 17 - Aug 18
Total with taxes and fees
The Perry Hotel & Marina Key West
The Perry Hotel & Marina Key West4.0 star property
Stock Island, 4.4 mi from Rockland Key
9.4 out of 10, Exceptional, (1,290 reviews)
9.4/10
Exceptional
(1,290 reviews)
"This place is AMAZING, everything was perfect.
Cleanness, staff, location, outstanding!!"
$192 nightly
The price is $216
$216 total
Jul 26 - Jul 27
Total with taxes and fees
Courtyard by Marriott Key West Waterfront
Courtyard by Marriott Key West Waterfront3.0 star property
Northside Resort, 6.1 mi from Rockland Key
8.8 out of 10, Excellent, (1,000 reviews)
8.8/10
Excellent
(1,000 reviews)
"Muy bien todo"
$173 nightly
The price is $195
$195 total
Jul 26 - Jul 27
Total with taxes and fees
Blue Flamingo Resort Key West
Blue Flamingo Resort Key West4.0 star property
New Town, 5.2 mi from Rockland Key
8.4 out of 10, Very Good, (2,539 reviews)
8.4/10
Very Good
(2,539 reviews)
"Wonderful hotel! A lot of things to do there. Shuttle bus was a plus. The only thing that I had a problem with was housekeeping. I had to call consistently for towels and also for them to pick up the garbage. And it will take a long time for them to come to the room. They never clean the bathroom nor mop the floor. And it had a lot of sand in the room. Other than that, the food and the stuff at the bar were great"
$179 nightly
The price is $201
$201 total
Aug 16 - Aug 17
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.