Rockland Key Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Rockland Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
Price was CA $904, price is now CA $715 per person
CA $715
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (2,316 reviews)
Perfect place to stay. We would have had so much fun if we had known about that place last year. We definitely will come back

Reviewed on Jul 9, 2026

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was CA $1,781, price is now CA $1,327 per person
CA $1,327
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,162 reviews)
I highly recommend this property! The place was beautiful and the pool and grounds really lovely. Can't wait to go back.

Reviewed on Jul 8, 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was CA $3,052, price is now CA $2,292 per person
CA $2,292
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (559 reviews)
We loved staying here and highly recommended it. Only thing that people might not like is the solo musicians play till 11pm every night. We didn’t mind it since we are not early birds.

Reviewed on Jun 7, 2026

Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Price was CA $1,579, price is now CA $1,214 per person
CA $1,214
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.2/10 Very good! (2,289 reviews)
The hotel has a great location, and I appreciated being able to check in early during the low season. However, the room lacked privacy. It featured a sliding door leading to a so-called “private patio” that was actually open for anyone walking by to see inside. We also had an unsettling experience when someone entered our room without knocking. Additionally, the on-site restaurant was disappointing. As someone with food allergies, I was frustrated that the chef was unwilling to modify the dish I wanted to order.

Reviewed on Jul 9, 2026

Eden House

Eden House

4 out of 5
Key West Historic District
Price was CA $1,203, price is now CA $935 per person
CA $935
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (1,008 reviews)
Top notch place , clean and comfortable

Reviewed on Jul 8, 2026

Ready to book your vacation to Rockland Key?

 

Choose your dates

Rockland Key Hotel Deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $200 per night from Jul 16 to Jul 17
CA $200
CA $360 total
Jul 16 - Jul 17
includes taxes & fees
8.6/10 Excellent! (2,336 reviews)
"Perfect place to stay. We would have had so much fun if we had known about that place last year. We definitely will come back"

Reviewed on Jul 9, 2026

Beachside Resort & Residences
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 Jul 12 to Jul 13
CA $177
CA $279 total
Jul 12 - Jul 13
includes taxes & fees
8.4/10 Very good! (2,510 reviews)
"My favorite place I’ve stayed ever. My wife and I spent the first 3 nights of our honeymoon at the Blue Flamingo Resort. We spent most of one our days at the resort. Honestly, we could have stayed there the whole time but we booked a lot. We had the Oceanview King room. We loved the pool. We enjoyed ..."

Reviewed on Jul 8, 2026

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $258 per night from Aug 5 to Aug 6
CA $258
CA $393 total
Aug 5 - Aug 6
includes taxes & fees
8.8/10 Excellent! (3,435 reviews)
"3 pools to choose from."

Reviewed on Jul 9, 2026

Southernmost Beach Resort and Guesthouses
See all 3,281 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 $715. 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.

Explore a world of travel with Expedia

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