
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 $1,802, price is now $1,125 per person
$1,125
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop 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.

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $3,400, price is now $1,964 per person
$1,964
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop 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.

Fitch Lodge - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was $1,818, price is now $1,169 per person
$1,169
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop 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. Concierge services are provided for your convenience.

Southernmost House
Old Town Key West
Save 100% on your flight
Price was $3,465, price is now $2,296 per person
$2,296
per person
Apr 23 - Apr 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a terrace, and a picnic area are also offered.

Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $2,003, price is now $1,335 per person
$1,335
per person
May 4 - May 9
found 1 day ago
Roundtrip non-stop 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.
Top Rockland Key hotels deals

Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
$415 nightly
The price is $466 total per night
$466 total
Apr 13 - Apr 14
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

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$284 nightly
The price is $320 total per night
$320 total
Apr 19 - Apr 20
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

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$358 nightly
The price is $403 total per night
$403 total
Mar 23 - Mar 24
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

Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$413 nightly
The price is $465 total per night
$465 total
Mar 25 - Mar 26
Total with taxes and fees
This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool and free perks like continental breakfast and WiFi in public areas.
On private beach
Pool

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
$362 nightly
The price is $407 total per night
$407 total
Apr 12 - Apr 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

Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$321 nightly
The price is $361 total per night
$361 total
Mar 26 - Mar 27
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and perks like free self parking.
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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