Rockland Key Vacation Packages 2026 from $1,543

Rockland Key flight + hotel vacation packages

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

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,543

per person

Dec 20 - Dec 23

found 1 day 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.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,968

per person

Dec 27 - Dec 31

found 1 day 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.

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West

Save 100% on your flight

$2,635

per person

Dec 24 - Dec 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

An outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free.

Hyatt Vacation Club at Beach House, Key West

$3,459

per person

Dec 26 - Jan 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Self parking, concierge services, and barbecue grills are also on offer.

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Old Town Key West

Save 100% on your flight

$5,041

per person

Dec 30 - Jan 4

found 9 hours ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

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

Top Rockland Key hotels deals

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

$265 nightly

$298 total

Oct 7 - Oct 8

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.

Pool

Hot Tub

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$168 nightly

$189 total

Oct 7 - Oct 8

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.

Pool

Hot Tub

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$185 nightly

$208 total

Oct 7 - Oct 8

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

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$190 nightly

$214 total

Nov 1 - Nov 2

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

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$172 nightly

$193 total

Oct 7 - Oct 8

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

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$306 nightly

$344 total

Oct 13 - Oct 14

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.

On private beach

Pool

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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 $1,543 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.