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 Windward Pointe, Key West
9.6/10 Exceptional! (1,002 reviews)
Jan 9 - Jan 12
3 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 $1,180, price is now $684 per person
$684
per person
found 1 day ago
Such a nice property
Reviewed on Jun 3, 2025
4.0-star property
Oceans Edge Key West Resort, Hotel & Marina
9/10 Wonderful! (1,736 reviews)
Jan 10 - Jan 17
7 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,188, price is now $1,162 per person
$1,162
per person
found 1 day ago
great property, transportation to key west great, missing an additional dining option. Everything else was fantastic
Reviewed on Sep 21, 2025
3.5-star property
Hyatt Vacation Club at Beach House, Key West
9.4/10 Exceptional! (1,002 reviews)
Jan 28 - Feb 1
4 night stay
Boston (BOS) to Key West (EYW)
Delta • Non-stop • Coach
Key West (EYW) to Boston (BOS)
Spirit Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,410, price is now $770 per person
$770
per person
found 1 day 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)
Jan 10 - Jan 17
7 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Roundtrip • Coach
Price was $4,325, price is now $2,414 per person
$2,414
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
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
9.2/10 Wonderful! (1,044 reviews)
Jan 12 - Jan 17
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 $1,761, price is now $1,025 per person
$1,025
per person
found 1 day ago
Professional staff, lovely rooms
Reviewed on Oct 21, 2025
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
$145 nightly
The price is $164 total per night
$164 total
Nov 30 - Dec 1
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 or tickets, dry cleaning/laundry, 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
$181 nightly
The price is $204 total per night
$204 total
Dec 1 - Dec 2
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 concierge services, dry cleaning/laundry, and luggage storage. Other amenities at this beach hotel include a 24-hour gym, free WiFi in public areas, and a hot tub.
On private beach
Pool
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
5.07 mi from city center
$143 nightly
The price is $161 total per night
$161 total
Dec 14 - Dec 15
Total with taxes and fees
Guests staying at Hilton Garden Inn Key West / The Keys Collection enjoy an outdoor pool, a gym, and free WiFi in public areas. If you drive, self parking is USD 15 per day, and there's also a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with luggage storage, securing valuables, and tours or tickets. Additional amenities include a hot tub, meeting rooms, and a business center.
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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