Cayman Islands Vacations & Trips

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Photo by Cayman Islands Department of Tourism

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    Save up to ₩234,741 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top destinations in Cayman Islands

FlightsFlightsHotelsHotels

Seven Mile Beach

Seven Mile Beach

Cayman Islands Vacation

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 Vacation Package with Expedia. With hotels starting at ₩478,330 a night, and an impressive 1,517 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 Vacation 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 a Cayman Islands All Inclusive vacations and really put your feet up this vacation?

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 ₩324,508 per night from Nov 29 to Nov 30
₩324,508
₩478,330 total
Nov 29 - Nov 30
includes taxes & fees
9/10 Wonderful! (628 reviews)
Everything was great, specially the clean room and the staff attention!

Reviewed on Nov 13, 2025

Hampton by Hilton Grand Cayman Seven Mile Beach
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
West Bay Road, PO Box 32348 KY1-1209, Seven Mile Beach, Grand Cayman
The price is ₩914,424 per night from Dec 5 to Dec 6
₩914,424
₩1,284,670 total
Dec 5 - Dec 6
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
Top notch experience. Amazing staff the stand out factor. So friendly, so obviously happy to meet everyone’s needs. This feel good factor is so much harder to achieve than a great location or great facilities but it made the experience so much more enjoyable

Reviewed on Nov 13, 2025

The Ritz-Carlton, Grand Cayman
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 ₩635,420 per night from Dec 15 to Dec 16
₩635,420
₩889,882 total
Dec 15 - Dec 16
includes taxes & fees
9.6/10 Exceptional! (432 reviews)
Rooms were clean, staff was very friendly and they keep the resort clean.

Reviewed on Nov 9, 2025

Hotel Indigo Grand Cayman by IHG
See all 1,517 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 vacation package cost?
The most affordable Cayman Islands vacation package is , so your dream vacation 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 vacation 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 travelers.
How far in advance should I book my Cayman Islands vacation?
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 vacation rentals like oceanfront condos and spacious residences. You've got choices galore!
Can I choose my airline with a Cayman Islands Expedia vacation package?
Expedia offers access to more than 550 airline partners globally, so you certainly can. Simply choose your favorite carrier and craft the perfect Cayman Islands escape.
If I'm not able to travel, can I cancel my Cayman Islands vacation 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.