
Deals on vacations and trips to Rockland Key
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Rockland Key flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.

The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $2,129, price is now $1,404 per person
$1,404
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a 24-hour gym.

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $3,696, price is now $2,101 per person
$2,101
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $2,348, price is now $1,407 per person
$1,407
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.

Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $2,485, price is now $1,588 per person
$1,588
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.

Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $3,464, price is now $2,296 per person
$2,296
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-in.
Top Rockland Key hotels deals

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$327 nightly
The price is $368 total per night
$368 total
Jan 14 - Jan 15
Total with taxes and fees
This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.
On private beach
Pool

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
$520 nightly
The price is $585 total per night
$585 total
Jan 14 - Jan 15
Total with taxes and fees
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.
Pool
Spa

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$283 nightly
The price is $318 total per night
$318 total
Jan 14 - Jan 15
Total with taxes and fees
This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and an arcade/game room, and families will appreciate the picnic area. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.
Pool
Hot Tub

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
$317 nightly
The price is $357 total per night
$357 total
Jan 19 - Jan 20
Total with taxes and fees
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.
Pool
Pet friendly

Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
$491 nightly
The price is $553 total per night
$553 total
Jan 28 - Jan 29
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.
Pool
Pet friendly

DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
$368 nightly
The price is $415 total per night
$415 total
Jan 19 - Jan 20
Total with taxes and fees
This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free beach shuttle.
Pool
Free airport shuttle
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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