
Rockland Key Vacations from $788
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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 $1,162, price is now $788 per person
$788
per person
Apr 12 - Apr 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Not sensory friendly. Noise from landscaper tools (weedwacker in this case) directly behind our chairs at pool area 11 in the morning was very overstimulating for someone with Autism. Also, the smell of gas from this was not good either. This was on more than one occasion. More thought should be given to the time of day this is done.
Reviewed on Feb 15, 2026

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $3,526, price is now $2,412 per person
$2,412
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Great location, very clean room and excellent staff!! Only headache is parking, but that is a Key West thing.
Reviewed on Feb 16, 2026

Havana Cabana at Key West
New Town
Save 100% on your flight
Price was $1,451, price is now $1,013 per person
$1,013
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (1,749 reviews)
Fantastic vibes - I would definitely stay there again! Front desk staff was super friendly and helpful, the pool was beautiful, and breakfast was tasty. There were a few maintenance items in the room that need to be addressed, but the hotel seems to be refreshing all of the rooms so I imagine those things are being handled. One item of note is that we had difficulty with the shower in our room - the water temp would fluctuate during the shower (randomly becoming hotter and colder). Overall, I’ll definitely return!
Reviewed on Feb 16, 2026

Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
Save 100% on your flight
Price was $1,172, price is now $828 per person
$828
per person
Apr 12 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.4/10 Very Good! (315 reviews)
Can’t beat the location. Ro
Reviewed on Jan 10, 2026

Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $2,123, price is now $1,503 per person
$1,503
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,844 reviews)
The amenities of the daily activities at each pool, location, and general vibe were phenomenal! W would stay here again!
Reviewed on Feb 17, 2026
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Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
$620 nightly
The price is $698 total per night from Mar 19 to Mar 20
$698 total
Mar 19 - Mar 20
Total with taxes and fees
8.8/10 Excellent! (3,084 reviews)
The amenities of the daily activities at each pool, location, and general vibe were phenomenal! W would stay here again!
Reviewed on Feb 17, 2026

Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$370 nightly
The price is $416 total per night from Mar 16 to Mar 17
$416 total
Mar 16 - Mar 17
Total with taxes and fees
8/10 Very Good! (2,082 reviews)
Room was clean although housekeeping was extremely slow.
Reviewed on Feb 17, 2026

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$422 nightly
The price is $474 total per night from Mar 11 to Mar 12
$474 total
Mar 11 - Mar 12
Total with taxes and fees
9/10 Wonderful! (1,812 reviews)
Excellent
Reviewed on Feb 17, 2026
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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