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
Orchid Key Inn - Adults Only
Old Town Key West
9.8/10 Exceptional! (1,001 reviews)
Sep 8 - Sep 14
6 night stay
Boston (BOS) to Key West (EYW)
Delta • Non-stop • Coach
Key West (EYW) to Boston (BOS)
American Airlines • Non-stop • Coach
Save 100% on your flight
per person
found 1 day ago
Great place. Very cool retro motel that’s been renovated. Room was a little small but very comfortable and clean. There’s a nice bar with great cocktails. Staff are friendly and attentive. The location was great. Central to everything and very walkable to most of the popular sites.
Reviewed on Jan 20, 2025
2.5-star property
The Grand Guesthouse
Old Town Key West
9.6/10 Exceptional! (1,001 reviews)
Aug 18 - Aug 23
5 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Fantastic host in historic district. Loved the location. Took great care of us!!!
Reviewed on Feb 28, 2025
3.5-star property
Almond Tree Inn Hotel - Adults Only
Old Town Key West
10/10 Exceptional! (1,001 reviews)
Aug 2 - Aug 8
6 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
As always, Almond Tree Inn was a bright spot in our latest trip to Key West. I’ve stayed here several times over the years and everything about Almond Tree is top notch, from the superbly attentive and friendly staff to the well-appointed and maintained property. You always feel special staying here and this trip was no exception. As Florida locals, we look forward to our stays with you each and every time- THANK YOU!
Reviewed on May 26, 2025
4.0-star property
The Perry Hotel & Marina Key West
9.4/10 Exceptional! (1,006 reviews)
Aug 3 - Aug 8
5 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
Excellent facility. The on site personnel were fabulous and the shuttle service is more than adequate.
Reviewed on Jan 5, 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
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, luggage storage, and tours or tickets. 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
8.17 mi from city center
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 47 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
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Free Cancellation
Reserve now, pay when you stay
6.63 mi from city center
Margaritaville Beach House Key West features an outdoor pool, a 24-hour gym, and a business center. The front desk is staffed 24/7 to help with luggage storage, tours or tickets, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach hotel include a banquet hall and an ATM.
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.
