Cayman Islands Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Cayman Islands Department of Tourism

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    Save up to NZ$616 when you book a flight and hotel together*

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Top destinations in Cayman Islands

FlightsFlightsHotelsHotels

Seven Mile Beach

Seven Mile Beach
FlightsFlightsHotelsHotels

George Town

George Town

Cayman Islands Holiday

A Caribbean paradise, the Cayman Islands will captivate you from the moment you set foot on the territory’s pristine shores.

Cayman Islands Hotel + Flight

Looking for an easy way to save some money on your getaway? Build your own Cayman Islands Holiday Package with Expedia. With hotels starting at NZ$812 a night, and an impressive 1,520 options to choose from, you'll get more bang for your Cayman Islands dollar than if you booked separately. We have everything you need for a fantastic Cayman Islands getaway — flights, hotels, car rental, tours and experiences.

Your Cayman Islands Holiday Itinerary

  • Day 1: Fly into Owen Roberts International Airport in Grand Cayman and start your adventure. For an unforgettable experience, head to Stingray City, where you can pet and feed gentle stingrays. Don’t miss the spectacular Cayman Crystal Caves either, where stalactite and stalagmite crystal structures await.

  • Day 2: A full-day tour of Grand Cayman Island is the perfect way to learn more about its many treasures, including Seven Mile Beach and the Cayman Turtle Farm. As the sun begins to set, cast away on a romantic sunset cruise with a rum cocktail in hand. Spend the rest of the evening discovering the vibrant nightlife of the capital George Town.

  • Day 3-4: Take a quick flight to Little Cayman Island and you’ll find yourself in a remote paradise. Explore wonders like South Hole Sound Lagoon, visit Booby Pond Nature Reserve and dive at Bloody Bay Wall Marine Park.

Cayman Islands Information

  • Don’t miss Pirate Week, more than a week’s worth of swashbuckling fun and festivities held each November. The festival kicks off with an invasion by sea as two pirate ships converge on George Town Harbour to take the local governor captive.

  • Getaways should be about rest and relaxation. Why not check in to aCayman Islands All Inclusive Resortand really put your feet up this holiday?

Our pick of the best Cayman Islands Hotel Deals

Hampton by Hilton Grand Cayman Seven Mile Beach

Hampton by Hilton Grand Cayman Seven Mile Beach

4 out of 5
22 Piper Way Seven Mile Beach
Fully refundableReserve now, pay when you stay
The price is NZ$812 per night from 13 Jan to 14 Jan
NZ$812
13 Jan - 14 Jan
includes taxes & fees
9.2/10 Wonderful! (670 reviews)
Great Hotel and Staff. Clean, modern rooms, amenities were great such as Breakfast included, Towel services, Beach access, shuttle service to most close locations. WE had a great stay!!!

Reviewed on 30 Dec 2025

Hampton by Hilton Grand Cayman Seven Mile Beach
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
389 West Bay Road Seven Mile Beach Grand Cayman
The price is NZ$1,194 per night from 19 Jan to 20 Jan
NZ$1,194
19 Jan - 20 Jan
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
The room was very clean. Hotel staff helpful. The extra classes that were added in over the holidays were a wonderful addition! This should be done routinely! We participated in a paint and sip class, an empanada making class and more. The fitness room, however, is in need of updates and mold eradication. ...

Reviewed on 1 Jan 2026

Grand Cayman Marriott Resort
Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
32 Seafire Way Seven Mile Beach West Bay
The price is NZ$1,022 per night from 6 Jan to 7 Jan
NZ$1,022
6 Jan - 7 Jan
includes taxes & fees
9.6/10 Exceptional! (459 reviews)
Staff are amazing, best service ever!

Reviewed on 30 Dec 2025

Hotel Indigo Grand Cayman by IHG
See all 1,520 properties in Cayman Islands
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 Cayman Islands holiday package cost?
The most affordable Cayman Islands holiday package is , so your dream holiday can become a reality — without the high price tag. Bundle flights, hotels and car rentals to build a package that suits your travel style.
How do I get a cheap travel package to Cayman Islands?
Combine your hotels and flights, toss in extras such as activities, and save with a Cayman Islands holiday package. You won't just score amazing discounts on your escape — you'll have plenty of choice at your fingertips too. When you book through Expedia, you'll have your pick of over 550 airlines and 1 000 000 hotels around the world. Your next affordable adventure starts right here, right now!
Where should I stay in Cayman Islands?
Boatswains Beach is one of the things that lures wanderers to Cayman Islands, so it should come as no surprise that many book their hotel in West Bay.
What are the top hotels in Cayman Islands?
Grand Cayman Marriott Resort and The Locale Hotel Grand Cayman know how to make their guests feel at home in Seven Mile Beach. If your travel plans also include North Side, look up The Westin Grand Cayman Seven Mile Beach Resort & Spa and Sunshine Suites Resort. Both are top picks with travellers.
How far in advance should I book my Cayman Islands holiday?
It's hard to pick the ideal time for airfares, but we generally suggest the earlier, the better. Most international flights on Expedia become available to compare up to 12 months in advance. If you can't book early, don't fret. Bargain prices appear from time to time just weeks before departure dates.
What does an Expedia Cayman Islands travel package include?
Packages include rental cars, flights and hotels, but you can mix and match them to create your perfect Cayman Islands getaway. You can also add on a few tours and activities once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll score discounts you won't find elsewhere.
What should I know before booking a Cayman Islands travel package?
Locking in all the parts of your trip together is a great way to save. Bundle your car rentals, airfares and hotels into a neat package. But your options don't end at hotels. Expedia has all types of properties, including holiday homes like oceanfront condos and spacious residences. You've got choices galore!
Can I choose my airline with a Cayman Islands Expedia holiday package?
Expedia offers access to more than 550 airline partners globally, so you certainly can. Simply choose your favourite carrier and craft the perfect Cayman Islands escape.
If I'm not able to travel, can I cancel my Cayman Islands holiday package?
Because we understand life can throw you a few curveballs, the answer is yes. For further details, head to our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to change or cancel it for free. Your hotel, airline or car rental company may impose a fee if your booking is older than that.

Discover the most popular places to visit in Cayman Islands

Port of Georgetown

Port of Georgetown

Explore the waterfront of Port of Georgetown and enjoy other activities such as snorkelling in George Town. Stroll along the area's seaside or simply savour its seafood restaurants.

Port of Georgetown
Seven Mile Beach

Seven Mile Beach

Why not spend a lazy afternoon at Seven Mile Beach during your trip to Seven Mile Beach? Stroll along the area's seaside or simply savour its seafood restaurants.

Seven Mile Beach
Spotts Beach

Spotts Beach

If a restful holiday is part of your travel plans, Spotts Beach might be the perfect place to visit during your trip to Savannah. Wander the parks and seaside while you're in the area.

Spotts Beach

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.