Pirates Cove Vacations from ¥291,042

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The Latest Pirates Cove Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

¥291,042
per person
Oct 26 - Nov 1
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Key West (EYW)
9.4/10 Exceptional! (1,335 reviews)
The Key West Hotel

The Key West Hotel

Key West Historic District
¥425,806
per person
Oct 26 - Nov 1
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Key West (EYW)
9.2/10 Wonderful! (562 reviews)
Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
¥417,416
per person
Oct 26 - Nov 1
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Old Town Key West
¥582,324
per person
Oct 26 - Nov 1
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Key West (EYW)
10/10 Exceptional! (1 review)
Loved the closeness to Duval st and the privacy

Reviewed on Oct 17, 2025

Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool

¥774,934
per person
Oct 26 - Nov 1
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Key West (EYW)
10/10 Exceptional! (1 review)
Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay

Reviewed on Jan 20, 2025

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
A wooden pier extending into calm waters, with a covered area at the end.

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.

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Silver Shores

If you're looking for some top things to see and do in Silver Shores and surrounding area, you can visit Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill.

A white speedboat on a blue ocean with a tropical island in the background.

Key Largo Village

While Key Largo Village might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Jimmy Johnson's Big Chill and Jacob's Aquatic Center.

An aerial view of a coastal area with RVs parked along the shore, a small beach, and a clear view of the ocean.

Key Largo Park

Though Key Largo Park might not have many top sights, you can venture to the surrounding area to see attractions like Jimmy Johnson's Big Chill and Jacob's Aquatic Center.

A bridge over a river with boats docked along the shore.

Cross Key Waterways

While Cross Key Waterways might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like MarineLab Undersea Laboratory and Caribbean Club Bar.

Pirates Cove Hotel Deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
¥23,809
¥38,471 total
Sep 7 - Sep 8
includes taxes & fees
Cheeca Lodge & Spa
Reefhouse Resort & Marina

Reefhouse Resort & Marina

103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
¥34,994
¥45,761 total
Sep 2 - Sep 3
includes taxes & fees
Reefhouse Resort & Marina
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

97000 Overseas Hwy Key Largo FL
¥37,867
¥51,409 total
Sep 28 - Sep 29
includes taxes & fees
8.6/10 Excellent! (1,179 reviews)
"Loved the overall Resort! The beach thenchair"

Reviewed on Sep 1, 2026

Baker's Cay Resort Key Largo, Curio Collection by Hilton
See all 2,508 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.

Frequently asked questions

How much does a Pirates Cove vacation package cost?
Handcraft your Pirates Cove package from as low as ¥291,042. 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.