Rockland Key Vacation Packages 2026 from $1,805

Rockland Key flight + hotel vacation packages

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

The Marker Key West Harbor Resort

Key West Historic District

Save 100% on your flight

$1,805

per person

Dec 24 - Dec 28

found 2 days ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This smoke-free hotel features 3 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,265

per person

Dec 24 - Dec 28

found 2 days ago

Roundtrip 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.

Orchid Key Inn - Adults Only

Old Town Key West

Save 100% on your flight

$1,843

per person

Dec 24 - Dec 28

found 2 days ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the hot tub and free continental breakfast each morning. Self parking, a garden, and dry cleaning are also offered.

Amelia Home by Avantstay In Historic Old Town w/ Pool

Old Town Key West

$3,528

per person

Jan 14 - Jan 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

An outdoor pool is featured at this cottage, along with free WiFi in public areas and barbecue grills.

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$2,085

per person

Dec 24 - Dec 28

found 2 days ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

2 outdoor pools, 2 bars/lounges, and a restaurant are among this bed & breakfast's featured amenities. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the poolside bar and enjoy the free cooked-to-order breakfast each morning.

Top Rockland Key hotels deals

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$275 nightly

$310 total

Oct 25 - Oct 26

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like a free airport shuttle. You'll appreciate the hot tub, poolside bar, and concierge services.

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$236 nightly

$265 total

Oct 30 - Oct 31

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.

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$166 nightly

$187 total

Oct 25 - Oct 26

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 a playground, 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.

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

$207 nightly

$232 total

Oct 25 - Oct 26

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.

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$193 nightly

$218 total

Oct 25 - Oct 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.

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$284 nightly

$320 total

Oct 28 - Oct 29

Total with taxes and fees

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.

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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 $1,805 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.