
Rockland Key Vacation Packages
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3.0-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (564 reviews)
Dec 6 - Dec 13
7 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 $4,653, price is now $2,912 per person
$2,912
per person
found 1 day ago
Property was everything as described, clean, in the heart of the excitement that is Key West
Pool was refreshing and close to tiki bar and local entertainment.
The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w
May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine
Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity
Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator
We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer
Reviewed on Oct 6, 2026

3.0-star property
Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay
Beachside
No reviews
Jan 8 - Jan 15
7 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 $3,334, price is now $2,462 per person
$2,462
per person
found 16 hours ago

3.0-star property
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Old Town Key West
10/10 Exceptional! (1 review)
Nov 29 - Dec 5
6 night stay
Boston (BOS) to Key West (EYW)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $3,879, price is now $2,870 per person
$2,870
per person
found 1 day ago
Loved the closeness to Duval st and the privacy
Reviewed on Oct 17, 2025

4.0-star property
The Marker Key West Harbor Resort
Key West Historic District
9.2/10 Wonderful! (1,024 reviews)
Dec 27 - Jan 2
6 night stay
Boston (BOS) to Key West (EYW)
Delta • Non-stop roundtrip • Coach
Price was $5,442, price is now $4,083 per person
$4,083
per person
found 1 day ago
Love this place!!!
Reviewed on Oct 24, 2026
Top rated hotels for your Rockland Key vacation package

Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
6.64 mi from city center
$255 nightly
The price is $287 total per night
$287 total
Oct 26 - Oct 27
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 dry cleaning/laundry, concierge services, 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 a gift shop.
Pool
Hot Tub

Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
5.58 mi from city center
$219 nightly
The price is $246 total per night
$246 total
Nov 15 - Nov 16
Total with taxes and fees
At Havana Cabana at Key West , guests have access to an outdoor pool, free WiFi in public areas, and a hot tub. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to assist with securing valuables, dry cleaning/laundry, and concierge services. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a meeting room, a terrace, and an ATM.
Pool
Hot Tub

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
$166 nightly
The price is $187 total per night
$187 total
Oct 26 - Oct 27
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.
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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