Rockland Key Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Rockland Key Vacation Deals

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

Coconut Beach Resort

2.5 out of 5
Old Town Key West
Price was CA $2,457, price is now CA $1,815 per person
CA $1,815
per person
Dec 11 - Dec 14
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (227 reviews)

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was CA $5,268, price is now CA $3,309 per person
CA $3,309
per person
Jan 7 - Jan 12
found 15 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Key West Historic District
Price was CA $3,970, price is now CA $2,873 per person
CA $2,873
per person
Jan 7 - Jan 12
found 15 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.2/10 Wonderful! (1,033 reviews)
Doesn't present in real life like it does online. Hallways were hot. Pools were very small and we felt like sardines in a bathtub. The room itself was styled well.

Reviewed on Nov 6, 2026

The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Price was CA $4,829, price is now CA $3,513 per person
CA $3,513
per person
Jan 7 - Jan 12
found 15 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was CA $4,888, price is now CA $3,581 per person
CA $3,581
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.8/10 Exceptional! (1,001 reviews)

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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 $321 per night from Nov 18 to Nov 19
CA $321
CA $450 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 $202 per night from Nov 29 to Nov 30
CA $202
CA $316 total
Nov 29 - Nov 30
includes taxes & fees
9/10 Wonderful! (1,899 reviews)
"Clean comfortable room, helpful van drivers and van service. Great staff."

Reviewed on Nov 6, 2026

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 $175 per night from Nov 15 to Nov 16
CA $175
CA $276 total
Nov 15 - Nov 16
includes taxes & fees
8.6/10 Excellent! (2,775 reviews)
"Really nice spot. Great for families and large groups"

Reviewed on Nov 6, 2026

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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $1,815. 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.