Rockland Key Vacation Packages 2026 from $1,801

Rockland Key flight + hotel vacation packages

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

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,801

per person

Nov 11 - Nov 14

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.

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

Old Town Key West

Save 100% on your flight

$2,252

per person

Dec 4 - Dec 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and concierge services are also provided.

Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay

Beachside

Save 100% on your flight

$2,027

per person

Dec 4 - Dec 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool is also provided.

Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

Old Town Key West

Save 100% on your flight

$1,807

per person

Dec 4 - Dec 10

found 1 day 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 and barbecue grills.

Amelia Home by Avantstay In Historic Old Town w/ Pool

Old Town Key West

Save 100% on your flight

$2,406

per person

Dec 3 - Dec 7

found 24 hours ago

Roundtrip flight included

Columbus (CMH) to Key West (EYW)

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

Top Rockland Key hotels deals

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$160 nightly

$180 total

Oct 1 - Oct 2

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

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$261 nightly

$294 total

Oct 7 - Oct 8

Total with taxes and fees

A full-service spa, 3 outdoor pools, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and laundry service. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a gym.

Pool

Spa

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$265 nightly

$298 total

Oct 1 - Oct 2

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

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$184 nightly

$207 total

Oct 1 - Oct 2

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

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$167 nightly

$188 total

Oct 1 - Oct 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

Pier House Resort & Spa

1 Duval St Key West FL

Free Cancellation

Reserve now, pay when you stay

$308 nightly

$346 total

Oct 7 - Oct 8

Total with taxes and fees

This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-in.

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 $1,801 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.