Rockland Key Vacation Packages 2026 from $1,097

Rockland Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Ibis Bay Beach Resort

Northside Resort

Save 100% on your flight

$1,097

per person

May 1 - May 8

found 1 day ago

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.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,349

per person

May 28 - Jun 1

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

$1,244

per person

May 1 - May 8

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.

The Reach Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$1,889

per person

May 1 - May 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This resort features a private beach, a full-service spa, and a restaurant. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. Enjoy the outdoor pool and unwind at the bar/lounge and poolside bar.

The Perry Hotel & Marina Key West

Save 100% on your flight

$1,323

per person

May 1 - May 8

found 1 day ago

Roundtrip non-stop 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.

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

$415 nightly

$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

$310 nightly

$349 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

$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

$465 total

Mar 25 - Mar 26

Total with taxes and fees

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

$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

$320 nightly

$360 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

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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.

Frequently asked questions

How much are vacation packages to Rockland Key?

If you like the idea of stress-free planning and big savings, our $1,097 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.