
Rockland Key Vacations from $800
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The Latest Rockland Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,272, price is now $800 per person
$800
per person
Mar 3 - Mar 6
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Signboards with building numbers can be useful. Also we could not figure out how to reach the pool area, so a few signs inside the elevator and near the stairs can be useful too.
Reviewed on Dec 29, 2025

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,142, price is now $1,198 per person
$1,198
per person
Mar 3 - Mar 6
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 Beach House, Key West
Save 100% on your flight
Price was $1,434, price is now $848 per person
$848
per person
Mar 5 - Mar 9
found 2 days ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
Clean rooms, nice landscaping and
Reviewed on Jan 1, 2026

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,415, price is now $877 per person
$877
per person
Mar 3 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
The room was good, the staff was very helpful and very kind
Reviewed on Dec 31, 2025

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,227, price is now $801 per person
$801
per person
Mar 3 - Mar 6
found 1 day ago
Roundtrip 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
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Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$310 nightly
The price is $349 total per night from Jan 4 to Jan 5
$349 total
Jan 4 - Jan 5
Total with taxes and fees
8.6/10 Excellent! (1,835 reviews)
Pool and hot tub were very nice,chicken walk was excellent! Great staff!!!!
Reviewed on Dec 26, 2025

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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