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! (1,218 reviews)
Nov 17 - Nov 21
4 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,343, price is now $941 per person
$941
per person
found 1 day ago
3.0-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (562 reviews)
Oct 15 - Oct 20
5 night stay
Asheville (AVL) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,706, price is now $2,184 per person
$2,184
per person
found 1 day ago
Great place to stay - highly recommend.
Reviewed on Aug 20, 2026
4.0-star property
The Gardens Hotel
Old Town Key West
9.8/10 Exceptional! (1,005 reviews)
Oct 15 - Oct 20
5 night stay
Asheville (AVL) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,053, price is now $1,402 per person
$1,402
per person
found 1 day ago
I honestly can’t rave enough about this place. From the first phone call to check out, everyone was so pleasant and helpful. The grounds are immaculately maintained, the property is absolutely beautiful. Tastefully whimsical !!!
The rooms are clean, the beds are comfy, all the way down to the linens. Everything is spot on. The location is just off Duval Street but you would never know it. It is so charming. Our waitress/bartender was the best! We met the owner and all I can say is she is the most delightful woman. You can see she has her heart in the establishment. There is even a wine gallery on site. I can’t wait to come back!
Reviewed on Sep 2, 2026
3.5-star property
Paradise Inn Key West - Adults Only
Old Town Key West
9.2/10 Wonderful! (1,014 reviews)
Oct 15 - Oct 20
5 night stay
Asheville (AVL) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,580, price is now $1,110 per person
$1,110
per person
found 1 day ago
The room I was given was not the room I booked on this website. Room Air Conditioner was loud and made it hard to sleep,TV was not working properly, bathroom needs some repair. Resort fee was added to the room rate in addition to the rate I paid on this website. Parking on site was and additional fee. Spoke to hotel staff No solution or action was taken to improve my stay. However it was close to Duval St. Most likely I will not be booking a stay in this place on my next visit to KW.
Reviewed on Sep 4, 2026
Top rated hotels for your Rockland Key vacation package
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
Reserve now, pay when you stay
8.14 mi from city center
$210 nightly
The price is $237 total per night
$237 total
Sep 13 - Sep 14
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, concierge services, and luggage storage. Other amenities at this spa 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
$195 nightly
The price is $219 total per night
$219 total
Sep 7 - Sep 8
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
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
6.64 mi from city center
$234 nightly
The price is $263 total per night
$263 total
Sep 20 - Sep 21
Total with taxes and fees
Guests of Margaritaville Beach House Key West have access to an outdoor pool, a 24-hour gym, and a hot tub. Airport transportation is made easy with a free airport shuttle (available on request). The 24-hour front desk has multilingual staff ready to assist with concierge services, dry cleaning/laundry, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach hotel include a business center, a terrace, and an ATM.
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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