
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)
Apr 2 - Apr 7
5 night stay
Boston (BOS) to Key West (EYW)
Spirit Airlines • Non-stop • Coach
Key West (EYW) to Boston (BOS)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,001, price is now $1,182 per person
$1,182
per person
found 1 day ago
The staff here were phenomenal! They were all so welcoming and kind. Made for a great experience!
Reviewed on Jan 21, 2026

2.5-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (505 reviews)
Apr 9 - Apr 12
3 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 $4,097, price is now $2,537 per person
$2,537
per person
found 2 days 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

3.5-star property
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Old Town Key West
8/10 Very Good! (2 reviews)
Apr 3 - Apr 9
6 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 $2,944, price is now $2,109 per person
$2,109
per person
found 1 day ago

4.0-star property
Havana Cabana at Key West
New Town
8.8/10 Excellent! (1,749 reviews)
Mar 1 - Mar 7
6 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,991, price is now $1,445 per person
$1,445
per person
found 1 day ago
The bartenders were wonderful.
Reviewed on Jul 2, 2025

2.5-star property
Coconut Beach Resort
Old Town Key West
9/10 Wonderful! (143 reviews)
Apr 2 - Apr 7
5 night stay
Boston (BOS) to Key West (EYW)
Spirit Airlines • Non-stop • Coach
Key West (EYW) to Boston (BOS)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,110, price is now $1,538 per person
$1,538
per person
found 1 day ago
We were upgraded to the oceanfront and it’s so beautiful. The cottage is nice and spacious.
Reviewed on Apr 23, 2024
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
$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, coffee/tea in a common area, and a computer station.

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
$560 nightly
The price is $630 total per night
$630 total
Feb 8 - Feb 9
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.

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
$445 nightly
The price is $501 total per night
$501 total
Jan 25 - Jan 26
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.
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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