
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! (1,010 reviews)
May 16 - May 19
3 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,214, price is now $828 per person
$828
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! (532 reviews)
May 2 - May 7
5 night stay
Atlanta (ATL) to Key West (EYW)
Delta • Roundtrip • Coach
Save 100% on your flight
Price was $2,908, price is now $1,648 per person
$1,648
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

3.5-star property
Hyatt Vacation Club at Windward Pointe, Key West
9.4/10 Exceptional! (1,003 reviews)
May 2 - May 7
5 night stay
Atlanta (ATL) to Key West (EYW)
Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,681, price is now $1,038 per person
$1,038
per person
found 1 day ago
Staff was fantastic, room and grounds very clean and well kept.
Reviewed on Feb 12, 2026

4.0-star property
The Reach Key West, Curio Collection by Hilton
Old Town Key West
8.6/10 Excellent! (1,004 reviews)
May 2 - May 7
5 night stay
Atlanta (ATL) to Key West (EYW)
Delta • Roundtrip • Coach
Price was $2,206, price is now $1,522 per person
$1,522
per person
found 1 day ago
Beautiful beach, great restaurant
Reviewed on Jan 22, 2026

4.0-star property
The Perry Hotel & Marina Key West
9.4/10 Exceptional! (1,220 reviews)
May 2 - May 7
5 night stay
Atlanta (ATL) to Key West (EYW)
Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,365, price is now $950 per person
$950
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

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
8.14 mi from city center
$575 nightly
The price is $647 total per night
$647 total
Apr 7 - Apr 8
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

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
5.04 mi from city center
$395 nightly
The price is $445 total per night
$445 total
Mar 10 - Mar 11
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

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
$328 nightly
The price is $369 total per night
$369 total
Mar 10 - Mar 11
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
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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