
Rockland Key Vacations from $506
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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
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,024 reviews)
This property is fantastic a little drive from old Key West and all the shops in water activities but so beautiful. The little pool shack named Abby Road really has good food and the area is just so pretty to sit and take your food and watch the ocean or the pool or the iguanas. The staff was amazing. We would absolutely go back if we are going to visit Key West again.
Reviewed on Aug 1, 2025



Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
per person
Oct 6 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,611 reviews)
The location was unique. We preferred a better room. The room choices were confusing and not clear. We were charged over $40/ day for parking when it is usually in the resort fee/VIP offering. One of the 2 EV chargers were not working and had to push for the staff to believe us.
We were not warned of the sewage smell from the beach.
Parking was limited and sometimes had to park in another section of the complex across and down the street. Surprised since we paid over $40/night for parking.
Reviewed on Aug 3, 2025
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Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$187 nightly
The price is $211 total per night from Aug 24 to Aug 25
$211 total
Aug 24 - Aug 25
Total includes taxes and fees
8.4/10 Very Good! (1,416 reviews)
"The unit was very spacious which was perfect for a family. The view from our unit was spectacular."
Reviewed on Aug 2, 2025

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$172 nightly
The price is $193 total per night from Sep 2 to Sep 3
$193 total
Sep 2 - Sep 3
Total includes taxes and fees
7.6/10 Good! (1,508 reviews)
"very nice place"
Reviewed on Aug 1, 2025

Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Fully refundable
$244 nightly
The price is $275 total per night from Aug 25 to Aug 26
$275 total
Aug 25 - Aug 26
Total includes taxes and fees
8.6/10 Excellent! (2,641 reviews)
"Location was perfect."
Reviewed on Jul 31, 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.
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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.