Rockland Key Vacation Packages

Save when you book Rockland Key package deals

Choose two or more items and save on your trip:

Flight and hotel packages to Rockland Key

Price found within the past 48 hours. Click for updated prices.
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
Key West Historic District
Save 100% on your flight
per person
Jul 13 - Jul 17
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An area shuttle and free self parking are featured at this bed & breakfast, along with an outdoor pool. WiFi in public areas is free. A business center, a terrace, and a garden are also on offer.
Beachside Resort & Residences

Beachside Resort & Residences

4 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This smoke-free hotel features a private beach, a marina, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the outdoor pool and visit the 2 bars/lounges and poolside bar for drinks.
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

5 out of 5
Old Town Key West
Save 100% on your flight
per person
Jul 13 - Jul 17
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free WiFi.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Save 100% on your flight
per person
Jul 6 - Jul 11
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
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.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
per person
Jul 13 - Jul 17
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. There's a restaurant and a bar/lounge for dining and drinks, and also a gym on site.

Top Rockland Key hotel deals

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue, Key West, FL
Free Cancellation
Reserve now, pay when you stay
The price is $175 per night
$175
per night
May 27 - May 28
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. There's a restaurant and a bar/lounge for dining and drinks, and also a gym on site.
Pet friendly
Breakfast available
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Free Cancellation
Reserve now, pay when you stay
The price is $251 per night
$251
per night
Jun 5 - Jun 6
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.
Pet friendly
Breakfast available
Havana Cabana at Key West - Adults Only

Havana Cabana at Key West - Adults Only

4 out of 5
3420 N. Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
The price is $183 per night
$183
per night
Jun 10 - Jun 11
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 spa tub and perks like free self parking.
Hot Tub
Pet friendly
Southernmost Beach Resort

Southernmost Beach Resort

4 out of 5
1319 Duval Street, Key West, FL
Free Cancellation
The price is $272 per night
$272
per night
Jun 19 - Jun 20
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.
Breakfast available
Pool
Fairfield Inn and Suites by Marriott Key West

Fairfield Inn and Suites by Marriott Key West

3 out of 5
2400 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
The price is $155 per night
$155
per night
May 27 - May 28
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy free perks like continental breakfast and free self parking. A poolside bar, a 24-hour front desk, and a terrace are also provided.
Breakfast included
Pool
La Concha Key West

La Concha Key West

4 out of 5
430 Duval St, Key West, FL
The price is $229 per night
$229
per night
May 27 - May 28
This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's an outdoor pool on site, and laundry facilities and concierge services are also offered.
Breakfast available
Pool
Don't see what you're looking for?
See all available properties in Rockland Key
View all properties
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.

Popular places to visit in Rockland Key

Image for Duval Street

Duval Street

4.5/5(3,475 reviews)

With a visit to Duval Street, a favorite shopping spot in Key West, you can search for that perfect souvenir. Wander the seaside or discover the area's beautiful sunsets.

Duval Street
Image for Mallory Square

Mallory Square

4.5/5(3,096 reviews)

Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.

Mallory Square
Image for Smathers Beach

Smathers Beach

4/5(1,151 reviews)

Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.

Smathers Beach

Frequently asked questions

How much are vacation packages to Rockland Key?
If you like the idea of stress-free planning and big savings, our $787 Rockland Key vacation package will be just the ticket. With your flights and hotels sorted, organizing your getaway around this famous attraction is easier than ever.
Where can I get the best vacation package deals for Rockland Key?
You’ll find an amazing range of Rockland Key package deals on Travelocity. With as many as 400 airlines and 1,000,000 properties worldwide, crafting your ultimate vacation will be simple.
Why should I book my Rockland Key vacation bundle with Travelocity?
Because life is one incredible journey, and we have everything you could hope for to help you along the way. With our superb service and Price Match Guarantee, you can book with confidence. And you can sleep easy while you’re away knowing we’re always available to chat via our 24/7 support.