
Rockland Key Vacations from $704
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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 Beach House, Key West
Save 100% on your flight
Price was $1,169, price is now $704 per person
$704
per person
Feb 3 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
The property was excellent, made us feel like we should have stayed longer. Will certainly come back.
Reviewed on Dec 20, 2025

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $4,049, price is now $2,759 per person
$2,759
per person
Feb 22 - Feb 28
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

The Gardens Hotel
Old Town Key West
Price was $3,110, price is now $2,135 per person
$2,135
per person
Mar 9 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
Loved it. The staff were very friendly and the place was classic Key West.
Reviewed on Dec 22, 2025

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Save 100% on your flight
Price was $3,453, price is now $2,381 per person
$2,381
per person
Jan 31 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.4/10 Very Good! (433 reviews)
When you have a suite for 6. You expect towels, wash cloths to be there everyday. Also not enough coffee or water cups. We should not of had to ask for this stuff everyday.
Reviewed on Dec 22, 2025

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays
Old Town Key West
Save 100% on your flight
Price was $4,385, price is now $3,089 per person
$3,089
per person
Mar 13 - Mar 20
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
No reviews
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View all tripsRockland Key Hotel Deals

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$302 nightly
The price is $340 total per night from Jan 4 to Jan 5
$340 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (1,804 reviews)
Excellent & Beautiful hotel The staff at the front desk is very kind & professional Thank you.
Reviewed on Dec 20, 2025

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$283 nightly
The price is $318 total per night from Jan 8 to Jan 9
$318 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
8/10 Very Good! (1,791 reviews)
Room was nice and the vibe was good. Pool was excellent and staff are very friendly. Could do better with breakfast. There were limited options and it took 30+ minutes to take our order.overall we enjoyed our stay.
Reviewed on Dec 22, 2025

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
$299 nightly
The price is $336 total per night from Jan 4 to Jan 5
$336 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.8/10 Excellent! (1,757 reviews)
Great View
Reviewed on Dec 22, 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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