Pirates Cove Vacations from $360
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Your Pirates Cove Vacation
Make travel planning easier by reserving a vacation package to Pirates Cove. Let us handle the small stuff, so you can concentrate on savoring everything this neighborhood can offer. Start your trip to Pirates Cove by visiting nearby attractions such as Jimmy Johnsons Big Chill, Bluefin Rock Harbor Marina and Jacobs Aquatic Center. Whatever your dream Pirates Cove vacation may look like, you can make it a reality with Expedia.
The Latest Pirates Cove Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Park Central South Beach
South Beach
Price was $1,418, price is now $656 per person
$656
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (116 reviews)
Clean, huge rooms - amazing staff and great facilities. The pools were fantastic and the perks like free bikes and pool towels really made it worth it.
Reviewed on Sep 29, 2025
Creekside Inn Islamorada
Save 100% on your flight
Price was $1,008, price is now $526 per person
$526
per person
Dec 3 - Dec 10
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,006 reviews)
We like the place, but were disappointed Mar Bar was closed. Not a big deal, but the construction along the waterfront wasn’t pretty.
Reviewed on Sep 28, 2025
Pelican Grand Beach Resort - A Noble House Resort
East Fort Lauderdale
Price was $1,932, price is now $1,018 per person
$1,018
per person
Nov 30 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (1,238 reviews)
We had a wonderful and would recommend the resort to friends.
Reviewed on Sep 29, 2025
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,098, price is now $586 per person
$586
per person
Dec 12 - Dec 15
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
Everyone and everything was great, such a great location to enjoy the whole island!
Reviewed on Sep 28, 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
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 John Pennekamp Coral Reef State Park.
Pirates Cove Hotel Deals
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $177 total per night from Oct 1 to Oct 2
$177 total
Oct 1 - Oct 2
Total with taxes and fees
9/10 Wonderful! (1,216 reviews)
"Great resort for vacation.I liked everything about This place except for parking lots for beach bungalows rooms"
Reviewed on Sep 28, 2025
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
$337 nightly
The price is $379 total per night from Oct 23 to Oct 24
$379 total
Oct 23 - Oct 24
Total with taxes and fees
8.6/10 Excellent! (1,027 reviews)
"Didn’t like the food options and the hotel needs some updates, specially the rooms. The rest was great."
Reviewed on Sep 23, 2025
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $178 total per night from Oct 2 to Oct 3
$178 total
Oct 2 - Oct 3
Total with taxes and fees
9/10 Wonderful! (1,534 reviews)
"Everything was perfect and beautiful"
Reviewed on Sep 23, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.