
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.

Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
Save 100% on your flight
Price was $636, price is now $403 per person
$403
per person
Nov 10 - Nov 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool, self parking, and concierge services are featured at this apartment. WiFi in public areas is free.

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,779, price is now $999 per person
$999
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a garden, and luggage storage are also offered.

Ridley House - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was $1,546, price is now $1,001 per person
$1,001
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this hotel, along with free WiFi in public areas and luggage storage. Enjoy the free buffet breakfast each morning. Concierge services are provided for your convenience.

Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $857, price is now $560 per person
$560
per person
Nov 10 - Nov 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, concierge services, and barbecue grills are also on offer.

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,610, price is now $1,066 per person
$1,066
per person
Dec 23 - Dec 27
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.
Top Rockland Key hotels deals

Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$235 nightly
The price is $264 total per night
$264 total
Oct 20 - Oct 21
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

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$163 nightly
The price is $183 total per night
$183 total
Oct 12 - Oct 13
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

Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Free Cancellation
$229 nightly
The price is $258 total per night
$258 total
Oct 29 - Oct 30
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

Parrot Key Hotel & Villas
2801 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$171 nightly
The price is $193 total per night
$193 total
Oct 13 - Oct 14
Total with taxes and fees
This eco-certified hotel features 4 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Unwind with a drink at the bar/lounge and enjoy perks like a free beach shuttle.
Pool
Free WiFi

DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$153 nightly
The price is $172 total per night
$172 total
Oct 12 - Oct 13
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

Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$143 nightly
The price is $161 total per night
$161 total
Oct 13 - Oct 14
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Unwind with a drink at the bar/lounge and enjoy perks like a free area shuttle.
Pool
Pet friendly
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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