Pirates Cove Holidays

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Photo by Patricia Smith
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Our guide on 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

Our pick of the best 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 NZ$551 per night from 23 July to 24 July
NZ$551
23 July - 24 July
includes taxes & fees
9/10 Wonderful! (1,475 reviews)
"An absolute dream! This place is absolutely amazing. Price point was great too. I can’t wait to come back!"

Reviewed on 24 Jun. 2025

Chesapeake Beach Resort
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NZ$444 per night from 6 July to 7 July
NZ$444
6 July - 7 July
includes taxes & fees
8.8/10 Excellent! (1,221 reviews)
"The property was very nicely landscaped and the pool and beach areas had comfortable furniture and were very inviting. The chickee huts provided nice shade. There is a seawall on the beach that separates the sand and water areas. There were pretty fire pits and music in the courtyard area which also ..."

Reviewed on 23 Jun. 2025

Amara Cay Resort
Cheeca Lodge & Spa
Cheeca Lodge & Spa
5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NZ$379 per night from 6 July to 7 July
NZ$379
6 July - 7 July
includes taxes & fees
9/10 Wonderful! (1,112 reviews)
"Amazing resort"

Reviewed on 24 Jun. 2025

Cheeca Lodge & Spa
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 holiday package cost?
Handcraft your Pirates Cove package from as low as . 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 holiday 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 Harbour 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 holiday?
While prices change frequently, we generally suggest booking your holiday 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 favourite 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 holiday, you're the one in control!
What should I know before booking a Pirates Cove travel package?
Bundling your bookings into a Pirates Cove holiday package is the most convenient way to organise 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 holiday 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 holiday package?
Whether it's your hotel or flight, you can cancel and rebook it. Locked in your Pirates Cove holiday 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.