Pirates Cove Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Patricia Smith

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
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Rock Harbor

1 out of top 10 points of interest in this area

While there might not be top attractions in Rock Harbor, you can explore the larger area and discover places like Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill.

Find hotels in Rock Harbor

Top hotels in Pirates Cove

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 3.304.662 ₫ per night from 30 Nov to 1 Dec
3.304.662 ₫
5.201.282 ₫ total
30 Nov - 1 Dec
includes taxes & fees
9.2/10 Wonderful! (1,587 reviews)
Excellent hotel

Reviewed on 26 Nov 2025

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 5.889.314 ₫ per night from 15 Dec to 16 Dec
5.889.314 ₫
8.405.723 ₫ total
15 Dec - 16 Dec
includes taxes & fees
9/10 Wonderful! (1,276 reviews)
We stayed in the newest section of the Cheeca Lodge. It is so incredibly nice! We had other family staying in the lagoon area. We enjoyed all the activities on the property as well. My nephew especially loved the par3 golf course. I really loved the staff at Cheeca Lodge too. Shelia, Amber and David ...

Reviewed on 26 Nov 2025

Cheeca Lodge & Spa
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
The price is 2.935.204 ₫ per night from 10 Dec to 11 Dec
2.935.204 ₫
4.043.883 ₫ total
10 Dec - 11 Dec
includes taxes & fees
8.8/10 Excellent! (1,131 reviews)
Place was great, clean, spacious, friendly staff, beautiful view affordable

Reviewed on 25 Nov 2025

Waterside Suites & Marina
See all 2,593 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 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 1null000null000 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.