
Rockland Key Vacations from $727
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The Latest Rockland Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,422, price is now $727 per person
$727
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (831 reviews)
The room and pool area were clean and pleasant. Good hospitality from staff including bartenders Alejandro and Jefferson. Unfortunately, the room remained humid due to the bathroom connection to the rest of the unit (above door) and wall A/C unit. Biggest drawback is the roosters on property and next door which do their best to wake you up at 4:00 AM. I suggest ear plugs and/or other sleep aids.
Reviewed on Dec 29, 2025

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Price was $1,593, price is now $800 per person
$800
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,044 reviews)
The staff was AMAZING!!! The property was immaculate!!! They made my while trip extraordinary!!
Reviewed on Jan 2, 2026

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,412, price is now $1,413 per person
$1,413
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Being right on Duval Street if city noise bothers you you might want to stay a block or two off Duval. But if you want all the action then this place is fantastic. Staff is great and the room was nicely appointed and very comfortable.
Reviewed on Dec 12, 2025

Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,174, price is now $729 per person
$729
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Room was clean, the grounds are very well kept. Only issue the front desk didn't explain housekeeping needed to be requested 24 hours in advance so we ended up with overflowing trash. Also requesting extra towels was a pain as most of the time we had to call multiple times. Overall we would stay again.
Reviewed on Jan 1, 2026

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $3,813, price is now $2,377 per person
$2,377
per person
Feb 12 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
A lovely but expensive resort with an average breakfast
Reviewed on Jan 2, 2026
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Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$323 nightly
The price is $363 total per night from Jan 6 to Jan 7
$363 total
Jan 6 - Jan 7
Total with taxes and fees
8.4/10 Very Good! (1,858 reviews)
The grounds are beautiful. Our room was a smaller room and it was nice but some things didn’t work properly. The toilet didn’t flush well, the shower head would turn on when filling the bathtub, tv would turn off randomly and the floors were dirty. Reasonably price in comparison to other places in ...
Reviewed on Jan 1, 2026

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$292 nightly
The price is $329 total per night from Jan 4 to Jan 5
$329 total
Jan 4 - Jan 5
Total with taxes and fees
8/10 Very Good! (1,803 reviews)
The room was very clean and comfortable. The $15.00 for parking your car was a little of the top tho! You should really give discounts for Florida Residence too, we drove 350 miles to come see Key West and to have to pay all the fees & parking fee is a bit much!
Reviewed on Dec 26, 2025

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$289 nightly
The price is $325 total per night from Jan 8 to Jan 9
$325 total
Jan 8 - Jan 9
Total with taxes and fees
8.8/10 Excellent! (1,763 reviews)
So many activities and amazing staff and service. The shuttle was very convenient. I would stay here again! Perfect for families. I felt safe. Very laid back environment.
Reviewed on Dec 26, 2025
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.
Find the Best Rockland Key Vacation Packages
Rockland Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
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