
Rockland Key Vacation Packages
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Top Rockland Key vacation package deals
Price found within the past 48 hours. Click for updated prices.

3.5-star property
Hyatt Vacation Club at Windward Pointe, Key West
9.6/10 Exceptional! (1,002 reviews)
Mar 22 - Mar 25
3 night stay
Boston (BOS) to Key West (EYW)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,201, price is now $769 per person
$769
per person
found 1 day ago
Pool and service was great!!! Staff always pleasant and helpful!
Reviewed on Dec 6, 2025

2.5-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (505 reviews)
Mar 18 - Mar 25
7 night stay
Albany (ALB) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,017, price is now $2,252 per person
$2,252
per person
found 1 day ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.
Reviewed on Jan 5, 2025

4.0-star property
Oceans Edge Key West Resort, Hotel & Marina
9/10 Wonderful! (1,736 reviews)
Mar 18 - Mar 25
7 night stay
Albany (ALB) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,601, price is now $1,537 per person
$1,537
per person
found 1 day ago
We LOVED the setting and the surrounding area! Absolutely beautiful!
Be aware the hotel IS in the airport landing zone. If you like to watch/hear commercial planes you'll be very happy.
Ask for a room on the top floor only - so you can (1) look over the marina AND (2) so you won't hear people moving chairs on their balcony above you.
The max/min air conditioning is centrally controlled. If you want it colder than 67, you will not be able to. Not sure what the max heat was.
Be extra vigilant about putting a thick towel on the floor to soak up any water that gets past the shower door. It WILL happen! Please do not slip on the wet tile floor!
Be aware that if you want/need a later checkout, they will charge you an additional $50/hour past their usual checkout time of 11am.
Be prepared for onsite meal expenses. They are very good, but they ARE on the pricy side.
Our particular room smelled strongly of smoke on arrival. I'm nearly POSITIVE we asked for a nonsmoking room as we both have underlying medical problems that preclude exposre to smoke. Perhaps call ahead to ENSURE you get a nonsmoking on arrival. The entire hotel was booked so we did not have any other choice.
Reviewed on Dec 28, 2025

4.0-star property
Southernmost Beach Resort and Guesthouses
Old Town Key West
8.6/10 Excellent! (2,844 reviews)
Mar 18 - Mar 25
7 night stay
Albany (ALB) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,773, price is now $1,762 per person
$1,762
per person
found 1 day ago
Billed me for parking when I didn’t have a car. Took several calls to try and resolve. Still haven’t received a refund. They were quick to take my money when I paid for the room but not so responsive in processing my refund.
Reviewed on Nov 1, 2025

4.0-star property
The Perry Hotel & Marina Key West
9.4/10 Exceptional! (1,151 reviews)
Mar 18 - Mar 25
7 night stay
Albany (ALB) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,315, price is now $1,517 per person
$1,517
per person
found 1 day ago
Check-in was as smooth as could be. Reps made sure we had access to a luggage cart right away. Property very clean. Room staff could not have been nicer. Would certainly book again
Reviewed on Aug 12, 2025
Top rated hotels for your Rockland Key vacation package

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
5.04 mi from city center
$321 nightly
The price is $361 total per night
$361 total
Jan 13 - Jan 14
Total with taxes and fees
Guests of Beachside Resort & Residences have access to a private beach, a marina, and an outdoor pool. If you drive, self parking is USD 25.00 per night, and there's also a free area shuttle. The front desk has multilingual staff on hand 24/7 to help with dry cleaning/laundry, tours or tickets, and luggage storage. Other amenities at this beach hotel include a 24-hour gym, free WiFi in public areas, and a hot tub.
On private beach
Pool

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
8.14 mi from city center
$435 nightly
The price is $489 total per night
$489 total
Jan 13 - Jan 14
Total with taxes and fees
Guests of Southernmost Beach Resort and Guesthouses have access to a full-service spa, 3 outdoor pools, and a gym. Self parking is offered for USD 53.75 per day. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, tours or tickets, and luggage storage. Other amenities at this beach hotel include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
5.16 mi from city center
$301 nightly
The price is $339 total per night
$339 total
Jan 13 - Jan 14
Total with taxes and fees
Blue Flamingo Resort Key West features 2 outdoor pools, karaoke, and a 24-hour gym. If you drive, self parking is USD 15.00 per night, and there's also a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with tours/tickets and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Other amenities at this family-friendly hotel include free WiFi in public areas, a hot tub, and meeting rooms.
Pool
Hot Tub
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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