
Rockland Key Vacations from $1,152
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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 $1,721, price is now $1,152 per person
$1,152
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
We stayed in a 2 bedroom villa and it was wonderful. Lots of space and had everything you needed. Right across from the ocean. The grounds were beautifully kept.
Reviewed on Feb 4, 2026

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $3,293, price is now $2,107 per person
$2,107
per person
Apr 17 - Apr 22
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Everything was great. I couldn’t complain about anything if I wanted to. Thanks for a great stay!
Reviewed on Jan 28, 2026

Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $1,974, price is now $1,316 per person
$1,316
per person
Apr 17 - Apr 22
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,844 reviews)
We splurged because it was a special occasion and I assumed given the room price and the high daily amenity fees that it would be fabulous. I don’t know what I paid for. Pools weren’t heated as promised, pool bars wouldn’t open and they’d send you to the beach cafe, there was talk on the website of free yoga—never saw that. The location is great but if you are gonna charge people $65 daily in amenity fees, there should be more amenities
Reviewed on Feb 5, 2026

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,798, price is now $1,222 per person
$1,222
per person
Apr 17 - Apr 22
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
The room was spotless. The resort was quiet and well maintained. The staff was very helpful. Check in and check out went very smoothly.
My only complaints were that I was unable to order in-room breakfast as the phone was never answered. Also, the edges of the mattress were pretty soft.
Reviewed on Feb 4, 2026

Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,725, price is now $1,224 per person
$1,224
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
Had a great time staying here for the second time! Staff is wonderful! Rooms are clean and beautiful
The grounds are lush and very well maintained!
Park here and Uber into town. Parking is terrible and expensive near Duvall street.
Reviewed on Feb 4, 2026
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Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
$530 nightly
The price is $596 total per night from Feb 8 to Feb 9
$596 total
Feb 8 - Feb 9
Total with taxes and fees
8.6/10 Excellent! (3,047 reviews)
Always our favorite spot. Staff is wonderful. Can’t beat the views and amenities.
Reviewed on Feb 1, 2026

Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
$389 nightly
The price is $437 total per night from Mar 8 to Mar 9
$437 total
Mar 8 - Mar 9
Total with taxes and fees
8/10 Very Good! (2,071 reviews)
Great ppl that work there!
Reviewed on Feb 5, 2026

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$418 nightly
The price is $471 total per night from Feb 9 to Feb 10
$471 total
Feb 9 - Feb 10
Total with taxes and fees
8.8/10 Excellent! (1,790 reviews)
Very clean room. Amazing view. Wonderful property!! Would absolutely stay here again!!!
Reviewed on Jan 30, 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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