
Rockland Key Vacations from $642
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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 $1,087, price is now $642 per person
$642
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Room was clean. A little wear and tear. Found the concierge to be very helpful. Ine of the front desk staff seemed a little unprofessional. Heard her scoffing at another customer's request. My family enjoyed the pool. It is large and heated. There are a lot of airplanes taking off and landing as the hotel is right next to the airport.
Reviewed on Jan 2, 2026

The Key West Hotel
Key West Historic District
Price was $2,705, price is now $1,463 per person
$1,463
per person
Feb 8 - Feb 12
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

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,259, price is now $756 per person
$756
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,044 reviews)
Room needs updates of lighting in bathroom and room, tv remote antiquated, dresser space was minimal. They need to assign an area for people with dogs. We were kept up all night with barking dogs. No hot water for a day. Grounds, pool, bar and exterior of building are good.
Reviewed on Jan 2, 2026

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,955, price is now $1,214 per person
$1,214
per person
Feb 8 - Feb 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Reception was courteous but housekeeping was terrible. Waitstaff was overwhelmed.
Reviewed on Jan 2, 2026

Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $1,577, price is now $1,024 per person
$1,024
per person
Feb 8 - Feb 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,844 reviews)
Amenities and best place to walk sunset off their pier.
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
$322 nightly
The price is $363 total per night from Jan 19 to Jan 20
$363 total
Jan 19 - Jan 20
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
$273 nightly
The price is $307 total per night from Jan 11 to Jan 12
$307 total
Jan 11 - Jan 12
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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