Rockland Key Vacation Packages

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Top Rockland Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Key West Historic District
Price was CA $2,049, price is now CA $1,535 per person
CA $1,535
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9.2/10 Wonderful! (1,033 reviews)

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was CA $3,091, price is now CA $1,990 per person
CA $1,990
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9.2/10 Wonderful! (564 reviews)
Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!

Reviewed on Oct 29, 2026

Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Old Town Key West
Price was CA $3,987, price is now CA $2,838 per person
CA $2,838
per person
Dec 18 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
8.8/10 Excellent! (227 reviews)

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

3 out of 5
Old Town Key West
Price was CA $7,463, price is now CA $5,638 per person
CA $5,638
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.8/10 Exceptional! (9 reviews)

The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Price was CA $7,614, price is now CA $5,872 per person
CA $5,872
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
9.8/10 Exceptional! (1,006 reviews)
Best place we have stayed. The staff was amazing location perfect and the room was perfect

Reviewed on Nov 3, 2026

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Rockland Key Hotel Deals

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $324 per night from Nov 18 to Nov 19
CA $324
CA $453 total
Nov 18 - Nov 19
includes taxes & fees
Margaritaville Beach House Key West
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Nov 29 to Nov 30
CA $203
CA $319 total
Nov 29 - Nov 30
includes taxes & fees
Havana Cabana at Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Nov 15 to Nov 16
CA $177
CA $278 total
Nov 15 - Nov 16
includes taxes & fees
Blue Flamingo Resort Key West
See all 3,288 properties in Rockland Key
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.
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Frequently asked questions

How much does a Rockland Key vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Rockland Key from just CA $1,535. And the more you bundle, the more you save. The vacation of your dreams has never been so affordable.
How do I get a cheap travel package to Rockland Key?
Creating your own Rockland Key vacation package with Expedia is a smart way to save. We have access to more than 550 air carriers and 1,000,000 properties all over the world. With such a fabulous range to choose from, you'll have no hassles creating your ideal escape.
Where should I stay in Rockland Key?
A getaway to Rockland Key isn't complete without paying a visit to Boca Chica Nude Beach, Key West Naval Station and Boca Chica Beach. Spend your nights near these popular sights and make sightseeing simple.
How far in advance should I book my Rockland Key vacation?
Savvy travelers will likely want to reserve their seats as early as possible. You can generally compare international airfares on Expedia up to 12 months before your intended flight. If you're booking at the last minute, there's no need to worry. Low prices sometimes appear in the last weeks before departure.
What does an Expedia Rockland Key travel package include?
Hotels, flights and rental cars — we have them covered. With Expedia, you can shape your Rockland Key travel package your way. All you have to do is figure out what you need. Once you've made your booking, you can add on fun things like activities and tours. The more you bundle, the more you save!
What should I know before booking a Rockland Key travel package?
You'll save big with an Expedia travel package. Combine your flights, rental cars and hotels and be rewarded with terrific discounts. Hotels aren't your only choice, however. Book with us and choose from island villas, cozy city apartments and even glamping tents!
Can I choose my airline with a Rockland Key Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation packages give you the freedom to take your pick of available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Rockland Key vacation package?
Certainly, and we'll help you every step of the way. You may be able to change or cancel your Rockland Key vacation package at no cost if you booked in the last 24 hours. But you may be charged a fee by your hotel, airline or car rental company if your booking is older than that. If life throws you a curveball, have a look at our Customer Service Portal for further information.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.