
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)
Jan 29 - Feb 3
5 night stay
Boston (BOS) to Key West (EYW)
Spirit Airlines • Non-stop • Coach
Key West (EYW) to Boston (BOS)
Delta • Non-stop • Coach
Save 100% on your flight
Price was $1,708, price is now $950 per person
$950
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

3.5-star property
Ella's Cottages - Key West Historic Inns
Old Town Key West
9.4/10 Exceptional! (390 reviews)
Feb 16 - Feb 21
5 night stay
Boston (BOS) to Key West (EYW)
Delta • Coach
Key West (EYW) to Boston (BOS)
American Airlines • Coach
Price was $2,811, price is now $1,408 per person
$1,408
per person
found 1 day ago
We chose this historic inn based on central location to everything we wanted in less than 15 min. Front desk staff (Dwight and others) are fantastic and always willing to listen and provide assistance. Fort Zachary Taylor Beach Park is walkable - 25 min (beach water shoes recommended due to rocks). We didn't need to rent any transportation as it was easier for us to walk it out, so I can't comment on parking since I didn't use it (it is limited at most places). We felt very safe walking around, even at night. We used a taxi to and from Key West airport (both drivers familiar with this inn). Room is clean. Both night stands have power and USB charging outlets. Excellent daily room service and Sunshine Breakfast basket hand delivered to your room. Duval Loop bus stop 14 (free) in front of inn (bus route loop is an hour long and two buses running to ensure next bus in 30 min), so this is another convenient option if walking isn't your thing.
Reviewed on Dec 17, 2024

4.0-star property
Oceans Edge Key West Resort, Hotel & Marina
9/10 Wonderful! (1,736 reviews)
Feb 16 - Feb 21
5 night stay
Boston (BOS) to Key West (EYW)
Delta • Coach
Key West (EYW) to Boston (BOS)
American Airlines • Coach
Price was $2,844, price is now $1,436 per person
$1,436
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

2.5-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (505 reviews)
Feb 16 - Feb 21
5 night stay
Boston (BOS) to Key West (EYW)
Delta • Coach
Key West (EYW) to Boston (BOS)
American Airlines • Coach
Price was $4,736, price is now $2,527 per person
$2,527
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
The Gardens Hotel
Old Town Key West
9.8/10 Exceptional! (1,000 reviews)
Feb 16 - Feb 21
5 night stay
Boston (BOS) to Key West (EYW)
Delta • Coach
Key West (EYW) to Boston (BOS)
American Airlines • Coach
Price was $3,301, price is now $1,762 per person
$1,762
per person
found 1 day ago
Paradise in paradise. Truly beautiful grounds, very special place.
Reviewed on Sep 25, 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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