Pirates Cove Vacations from $314
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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.
The Penguin Hotel
South Beach
Save 100% on your flight
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,329 reviews)
Pour mon séjour je donnerai une note de 3 sur 5, en raison du système de climatisation très brouillant. Le personnel m'a paru aussi un peu distant, aimable à la limite.
Reviewed on Jul 22, 2025
The Shelborne By Proper, a Member of Design Hotels
South Beach
per person
Sep 24 - Sep 29
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.6/10 Exceptional! (5 reviews)
Quiet.Lobby was nice and smelled amazing. Staff was good. Loved the gym/studio.
Dislikes: No hot water in the shower. Lobby smelled amazing but wasn’t consistent throughout the building.
Reviewed on Jul 17, 2025
President Hotel
South Beach
Save 100% on your flight
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,636 reviews)
One thing I didn’t like is the hidden fees I thought when I paid with Expedia, everything would be covered but when I went there, they charge me another $130 for daily fees read the fine print everything is not included
Reviewed on Jul 20, 2025
iCoconutGrove Vacation Rentals
Coconut Grove
per person
Sep 29 - Oct 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,000 reviews)
The property was in a very populated area with lots of shops, restaurants and nightlife (if that’s your thing). The studio was very clean and there were no issues at all. Unlike hotel rooms, I could not hear what was happening right next door, so it was quiet as well.
I would stay here again.
Reviewed on Jul 12, 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 Jacob's Aquatic Center.
Pirates Cove Hotel Deals
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
$320 nightly
The price is $361 total per night from Aug 21 to Aug 22
$361 total
Aug 21 - Aug 22
Total includes taxes and fees
9/10 Wonderful! (1,137 reviews)
"Stayed here for one night. Unfortunately the weather wasn’t great so we didn’t get to experience the pool areas and such. We walked around the grounds at night in the rain and it was still breath taking. Would love to stay longer the next time I am back in the area."
Reviewed on Jul 20, 2025
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$216 nightly
The price is $244 total per night from Aug 12 to Aug 13
$244 total
Aug 12 - Aug 13
Total includes taxes and fees
9/10 Wonderful! (1,486 reviews)
"One of my favorite places to have a relaxing trip with the family"
Reviewed on Jul 21, 2025
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy, Key Largo, FL
$364 nightly
The price is $409 total per night from Aug 12 to Aug 13
$409 total
Aug 12 - Aug 13
Total includes taxes and fees
8.6/10 Excellent! (1,005 reviews)
"My experience at Baker’s Cay was outstanding from start to finish. The room was very clean, well-prepared, and super comfortable. You can really tell they pay attention to every detail. The beach area was one of my favorite spots—beautiful, peaceful, and full of fun ways to enjoy the ocean and surroundings. ..."
Reviewed on Jul 13, 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.