
Rockland Key Vacations from $846
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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 $1,371, price is now $846 per person
$846
per person
Jan 19 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
We enjoyed the beautiful property.
Reviewed on Dec 7, 2025

Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,375, price is now $849 per person
$849
per person
Jan 12 - Jan 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
The Hyatt at Windward Pointe is a beautiful property with outstanding views of the water. The pool area and grounds are clean & well taken care of. Our room was very spacious, clean and had everything we needed. We also like the close proximity to airport and Smathers Beach.
Reviewed on Dec 5, 2025

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,524, price is now $1,666 per person
$1,666
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Room was great and clean.
Reviewed on Dec 7, 2025

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,412, price is now $974 per person
$974
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Clean room, great and friendly staff, great pools, easy parking, everything was great
Reviewed on Dec 7, 2025

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,731, price is now $1,196 per person
$1,196
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,044 reviews)
Room was very private everything was within walking distance. Only down side was the breakfast it was very basic.
Reviewed on Dec 6, 2025
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Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $247 total per night from Dec 15 to Dec 16
$247 total
Dec 15 - Dec 16
Total with taxes and fees
8.6/10 Excellent! (1,734 reviews)
Staff very courteous! We arrived very early- hoping we could at least chk our bags before going to lunch ( 2 couples- booking two rooms). Our friends' room was already available .We were told ours would be ready soon. We had a lovely, long, leisurely lunch at Chicken Walk. Our room still wasnt ready ...
Reviewed on Dec 3, 2025

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$166 nightly
The price is $187 total per night from Dec 14 to Dec 15
$187 total
Dec 14 - Dec 15
Total with taxes and fees
8/10 Very Good! (1,750 reviews)
Love this place rooms are wonderful pool view is great. Employees all speak English and are so nice and helpful. Especially Flora
Reviewed on Dec 5, 2025

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $227 total per night from Dec 16 to Dec 17
$227 total
Dec 16 - Dec 17
Total with taxes and fees
8.8/10 Excellent! (1,747 reviews)
Very nice clean and big room. Great view over the pools and harbor.
Reviewed on Dec 4, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


















