Pirates Cove Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Pirates Cove

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was CA $2,295, price is now CA $1,237 per person
CA $1,237
per person
Apr 27 - May 3
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Courteous staff. Great location

Reviewed on Feb 7, 2026

Creekside Inn

Creekside Inn

2.5 out of 5
Price was CA $3,051, price is now CA $1,335 per person
CA $1,335
per person
Apr 22 - Apr 29
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
Room was clean, spacious with a wonderful canal view.

Reviewed on Jan 27, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was CA $39,217, price is now CA $21,441 per person
CA $21,441
per person
Mar 19 - Mar 26
found 7 hours ago
Roundtrip flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very Good! (1 review)
President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was CA $2,262, price is now CA $1,255 per person
CA $1,255
per person
Apr 27 - May 3
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very Good! (997 reviews)
Stayed 5 nights. Room was done only once

Reviewed on Feb 11, 2026

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was CA $15,963, price is now CA $8,943 per person
CA $8,943
per person
Apr 27 - May 3
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
9.4/10 Exceptional! (1,365 reviews)
Room very nice but not very well designed. Bed and couch on a riser- not the floor- requiring a step up to get to each. Everytime you got up at night- a light would come on and stay on for 10 minutes. Safety so you don’t fall- but should we really have a bed on a riser? Found the light on disruptive to getting back to sleep. Very dark room- not well lit at all. No makeup mirror Slippery marble floor shower- ask for a rubber mat- which we finally got the day before our stay ended Great access to pool and beach Great service in hotel and beach Great service from the house car Very pleasant staff Mini bar beverages not cold- required ice to chill No ice machine- but they brought the ice to you if you called and requested Nice roof top pool but music was too loud to enjoy. Could not eat at Watr restaurant - roof top-due to the loud music Reserved a shower room to freshen up after check out our last day- but did not get one- had to use the gym for getting cleaned up for our flight- lot of disorganization around this entire situation. No one ever offered and explanation on what happened- did not have time to investigate- trying ti get to airport. Great location and vibe- we enjoyed our stay but would not stay here again.

Reviewed on Feb 11, 2026

Where to stay in Pirates Cove

Find the best Pirates Cove areas and neighborhoods for the activities you enjoy most. Learn more about Pirates Cove
Safety Harbor, Florida

Rock Harbor

1 out of top 10 points of interest in this area

While Rock Harbor isn't home to many top sights, Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill are some notable places to visit nearby.

Find hotels in Rock Harbor

Pirates Cove Hotel Deals

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $449 per night from Feb 12 to Feb 13
CA $449
CA $582 total
Feb 12 - Feb 13
includes taxes & fees
9.2/10 Wonderful! (1,665 reviews)
We loved this place. It’s small and easy to get around. Beautiful setting, watched the sunrise from bed, and the best hotel breakfast we’ve ever had.

Reviewed on Feb 3, 2026

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $483 per night from Feb 12 to Feb 13
CA $483
CA $643 total
Feb 12 - Feb 13
includes taxes & fees
9.2/10 Wonderful! (1,296 reviews)
Paradise away from Home!! Thank you!

Reviewed on Feb 7, 2026

Cheeca Lodge & Spa
Reefhouse Resort & Marina

Reefhouse Resort & Marina

3.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
The price is CA $419 per night from Feb 12 to Feb 13
CA $419
CA $525 total
Feb 12 - Feb 13
includes taxes & fees
9.2/10 Wonderful! (1,354 reviews)
Staff were great and very helpful. This is a beautiful resort!

Reviewed on Feb 6, 2026

Reefhouse Resort & Marina
See all 2,584 properties in Pirates Cove
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 Pirates Cove vacation package cost?
Handcraft your Pirates Cove package from as low as CA $1,237. Pick from any combination of rental cars, flights and hotels to put together the escape you've been dreaming of. Don't forget to add on one or two experiences!
How do I get a cheap travel package to Pirates Cove?
Combining your flight and hotel with Expedia won't just save precious time — it'll save you cash too. A Pirates Cove vacation package makes it easy to put together your perfect trip. With more than 550 airlines throughout the world to pick from, finding flights that suit your busy schedule will be no sweat. In addition to that, we have over 1,000,000 properties globally to choose from. Now that's what we call choice. Whatever your budget, Expedia puts the world within your reach.
Where should I stay in Pirates Cove?
A getaway to Pirates Cove isn't complete without paying a visit to Jimmy Johnsons Big Chill, Bakers Cay Resort Beach and Bluefin Rock Harbor Marina. Spend your nights close to these attractions and make sightseeing easy.
What are the top hotels in Pirates Cove?
Key Largo Gem On The Water With A Little Slice Of Heaven and Amazing Waterfront 2 Bed/1 Bath Private Fenced Home are a couple of the most sought-after hotels in Pirates Cove. Why not check out the amenities and rates at each and then decide?
How far in advance should I book my Pirates Cove vacation?
While prices change frequently, we generally suggest booking your vacation as soon as possible. Many international airfares become available on Expedia up to 12 months in advance. If circumstances have left you booking last minute, you might still be in luck. Cheap journeys to Pirates Cove sometimes appear in the weeks prior to departure.
What does an Expedia Pirates Cove travel package include?
Hotels, flights and a reliable car for your road trip adventures. Simply select your favorite bundle and get access to incredible deals. Once you've made your booking, add on a couple of tours and experiences and watch your savings pile up. When it comes to creating your Pirates Cove vacation, you're the one in control!
What should I know before booking a Pirates Cove travel package?
Bundling your bookings into a Pirates Cove vacation package is the most convenient way to organize your trip. Not only that, you'll save when you combine your flights, hotels and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a Pirates Cove Expedia vacation package?
Yes — that's the beauty of an Expedia package. You get to decide. We have access to more than 550 airline partners around the world, so you have options galore when putting together your Pirates Cove trip.
If I'm not able to travel, can I cancel my Pirates Cove vacation package?
Whether it's your hotel or flight, you can cancel and rebook it. Locked in your Pirates Cove vacation package in the last 24 hours? You may be able to make changes or cancellations for free. For older bookings, you may incur a charge from your airline, hotel or car rental company. For further information, visit our Customer Service Portal. We're here to help you each step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.