
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 Beach House, Key West
9.4/10 Exceptional! (1,002 reviews)
Mar 19 - Mar 22
3 night stay
Boston (BOS) to Key West (EYW)
Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,432, price is now $964 per person
$964
per person
found 12 hours ago
The property was truly amazing. We.rented a 2 bedroom villa and it was comfortable and very well decorated and equipped. The only complaint would be the " complimentary breakfast" needs to be better. It was only a selection of cruisants with water and orange juice. For the price spent, please add eggs, meat and coffee at least. Other than that, it was very nice
Reviewed on Sep 7, 2025

2.5-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (505 reviews)
Apr 3 - Apr 7
4 night stay
Allentown (ABE) to Key West (EYW)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,424, price is now $1,499 per person
$1,499
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)
Feb 20 - Feb 28
8 night stay
Allentown (ABE) to Key West (EYW)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $3,139, price is now $1,946 per person
$1,946
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
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
9.2/10 Wonderful! (1,044 reviews)
Apr 3 - Apr 7
4 night stay
Allentown (ABE) to Key West (EYW)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,776, price is now $1,136 per person
$1,136
per person
found 1 day ago
Great place! Great staff!
Reviewed on Dec 26, 2025

3.0-star property
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
9/10 Wonderful! (2 reviews)
Apr 3 - Apr 9
6 night stay
Boston (BOS) to Key West (EYW)
JetBlue Airways • Coach
Key West (EYW) to Boston (BOS)
Spirit Airlines • Coach
Price was $3,390, price is now $2,356 per person
$2,356
per person
found 23 hours ago
Top rated hotels for your Rockland Key vacation package

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
$346 nightly
The price is $389 total per night
$389 total
Jan 19 - Jan 20
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

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
8.14 mi from city center
$530 nightly
The price is $596 total per night
$596 total
Jan 26 - Jan 27
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

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
3.86 mi from city center
$321 nightly
The price is $362 total per night
$362 total
Jan 21 - Jan 22
Total with taxes and fees
Guests of Oceans Edge Key West Resort, Hotel & Marina have access to a marina, 6 outdoor pools, and a 24-hour gym. If you drive, self parking is USD 32.63 per night, and there's also an area shuttle. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, tours or tickets, and luggage storage. Other amenities at this luxury hotel include free WiFi in public areas, meeting rooms, and free use of bicycles.
Pool
Pet friendly
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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