
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.

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $2,028, price is now $1,135 per person
$1,135
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $3,857, price is now $2,151 per person
$2,151
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,792, price is now $1,724 per person
$1,724
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.

Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,623, price is now $1,632 per person
$1,632
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
An outdoor pool, self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $2,107, price is now $1,321 per person
$1,321
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Top Rockland Key hotels deals

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$212 nightly
The price is $239 total per night
$239 total
Dec 15 - Dec 16
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

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$166 nightly
The price is $187 total per night
$187 total
Dec 14 - Dec 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
$218 nightly
The price is $245 total per night
$245 total
Dec 14 - Dec 15
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

Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$153 nightly
The price is $172 total per night
$172 total
Dec 14 - Dec 15
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like a free area shuttle.
Pool
Hot Tub

Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
$250 nightly
The price is $282 total per night
$282 total
Dec 18 - Dec 19
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

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
$262 nightly
The price is $295 total per night
$295 total
Dec 16 - Dec 17
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
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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