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.
2.5-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (532 reviews)
May 22 - May 25
3 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop • Coach
Key West (EYW) to Boston (BOS)
Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,723, price is now $1,062 per person
$1,062
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
Havana Cabana at Key West
New Town
8.8/10 Excellent! (1,698 reviews)
Apr 22 - Apr 29
7 night stay
Boston (BOS) to Key West (EYW)
JetBlue Airways • Coach
Key West (EYW) to Boston (BOS)
American Airlines • Coach
Save 100% on your flight
Price was $2,076, price is now $1,303 per person
$1,303
per person
found 1 day ago
Very nice family oriented place.
Reviewed on Feb 2, 2026
4.0-star property
Southernmost Beach Resort and Guesthouses
Old Town Key West
8.8/10 Excellent! (3,103 reviews)
Apr 22 - Apr 29
7 night stay
Boston (BOS) to Key West (EYW)
JetBlue Airways • Coach
Key West (EYW) to Boston (BOS)
American Airlines • Coach
Save 100% on your flight
Price was $2,962, price is now $2,006 per person
$2,006
per person
found 1 day ago
Rooms was spotless ! An amazing resort !
Reviewed on Feb 23, 2026
4.0-star property
Blue Flamingo Resort Key West
New Town
8.2/10 Very Good! (1,957 reviews)
Apr 22 - Apr 29
7 night stay
Boston (BOS) to Key West (EYW)
JetBlue Airways • Coach
Key West (EYW) to Boston (BOS)
American Airlines • Coach
Save 100% on your flight
Price was $1,568, price is now $1,081 per person
$1,081
per person
found 1 day ago
The Blue Flamingo is an amazing a GEM in Key West, the location and property are simply fabulous, every employee always with a smile, cant mention all but will state Mr. Jose (Ambassador), Leidy, Irina, Skiff, David and all Waiters and Bartenders go over and beyond to make your stay memorable, Lobby and Reception, housekeepers, pool boys, all friendly and helpful. We will be back many times!
Reviewed on Nov 25, 2025
4.0-star property
The Reach Key West, Curio Collection by Hilton
Old Town Key West
8.6/10 Excellent! (1,004 reviews)
Apr 22 - Apr 29
7 night stay
Boston (BOS) to Key West (EYW)
JetBlue Airways • Coach
Key West (EYW) to Boston (BOS)
American Airlines • Coach
Save 100% on your flight
Price was $3,440, price is now $2,416 per person
$2,416
per person
found 1 day ago
Beautiful beach, great restaurant
Reviewed on Jan 22, 2026
Top rated hotels for your Rockland Key vacation package
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
8.14 mi from city center
$596 nightly
The price is $671 total per night
$671 total
Mar 24 - Mar 25
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 tours or tickets, dry cleaning/laundry, and luggage storage. Other amenities at this beach hotel include conference space, coffee/tea in a common area, and a computer station.
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
$346 nightly
The price is $389 total per night
$389 total
Mar 15 - Mar 16
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 concierge services 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
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
5.04 mi from city center
$375 nightly
The price is $422 total per night
$422 total
Mar 12 - Mar 13
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 luggage storage, dry cleaning/laundry, and concierge services. Other amenities at this beach hotel include a 24-hour gym, free WiFi in public areas, and a hot tub.
On private beach
Pool
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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