Pirates Cove Holidays from NZ$3,411

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Top Holiday Package Deals in Pirates Cove

Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was NZ$5,476, price is now NZ$3,411 per person
NZ$3,411
per person
12 Feb - 19 Feb
found 10 hours ago
Return direct flight included
Weyers Cave (SHD) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Room was good .. except for a dusty smell

Reviewed on 24 Dec 2025

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was NZ$9,055, price is now NZ$5,125 per person
NZ$5,125
per person
12 Feb - 19 Feb
found 10 hours ago
Return direct flight included
Weyers Cave (SHD) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Being right on Duval Street if city noise bothers you you might want to stay a block or two off Duval. But if you want all the action then this place is fantastic. Staff is great and the room was nicely appointed and very comfortable.

Reviewed on 12 Dec 2025

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
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Price was NZ$9,076, price is now NZ$5,830 per person
NZ$5,830
per person
12 Feb - 19 Feb
found 10 hours ago
Return direct flight included
Weyers Cave (SHD) to Key West (EYW)
9.4/10 Exceptional! (390 reviews)
The check in staff was not hospitable. The pool was not heated, and the couch in our suite was very dirty/dinghy. Location is great and property is beautiful. We had amazing staff at check out. I recommend staying at Winslows Bungalows their sister property. More pool options, bar, and impeccable customer service.

Reviewed on 20 Dec 2025

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Save 100% on your flight
Price was NZ$6,963, price is now NZ$4,548 per person
NZ$4,548
per person
12 Feb - 19 Feb
found 10 hours ago
Return direct flight included
Weyers Cave (SHD) to Key West (EYW)
9.2/10 Wonderful! (845 reviews)
Excellent location with access to all areas of the island either on foot or bus. Breakfast was staffed by Sonia who went out of her way to meet any requests. The staff were very friendly and helpful.

Reviewed on 21 Dec 2025

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was NZ$5,867, price is now NZ$3,884 per person
NZ$3,884
per person
12 Feb - 19 Feb
found 10 hours ago
Return direct flight included
Weyers Cave (SHD) to Key West (EYW)
9/10 Wonderful! (831 reviews)
Property location was excellent walkable. Staff was awesome. Breakfast was good. Air conditioner kept up! Loved our room and front porch!

Reviewed on 24 Dec 2025

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
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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

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$410 per night from 6 Jan to 7 Jan
NZ$410
6 Jan - 7 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (1,600 reviews)
Great chef that made breakfast to order! Resort was calming and relaxing!

Reviewed on 21 Dec 2025

Chesapeake Beach Resort
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

2.5 out of 5
527 Caribbean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
The price is NZ$321 per night from 8 Jan to 9 Jan
NZ$321
8 Jan - 9 Jan 2026
includes taxes & fees
8.4/10 Very Good! (1,654 reviews)
Room clean, beautiful setting, pleasant ambiance good restaurants! Staff friendly and courteous

Reviewed on 17 Dec 2025

Marina Del Mar Resort and Marina
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 NZ$328 per night from 4 Jan to 5 Jan
NZ$328
4 Jan - 5 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,171 reviews)
it was great. will stay there again.

Reviewed on 23 Dec 2025

Waterside Suites & Marina
See all 2,561 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 NZ$3,411. 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.