Cayman Islands Vacations & Trips from ￥412,859

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Photo by Cayman Islands Department of Tourism

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The Latest Cayman Islands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Wyndham Reef Resort Grand Cayman

Wyndham Reef Resort Grand Cayman

3.5 out of 5
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to George Town (GCM)
8.4/10 Very Good! (1,009 reviews)
Dated property, not as pictured when selecting a location to stay on line. Request made several times for fresh towels but was not done, went to front desk for assistance.

Reviewed on Jul 30, 2025

Black Urchin

Black Urchin

4.5 out of 5
Save 100% on your flight
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to George Town (GCM)
10/10 Exceptional! (2 reviews)
Property is Beautiful and very private. One downside is being so far from extracurricular activities

Reviewed on Mar 26, 2025

Club Suites at Rum Point

Club Suites at Rum Point

4 out of 5
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to George Town (GCM)
9.6/10 Exceptional! (24 reviews)
Amazing, beautiful property! Fantastic food, gorgeous pool! Can't wait to go back.

Reviewed on Jul 2, 2025

Galleon Villas by Hello Cayman Vacation

Galleon Villas by Hello Cayman Vacation

3.5 out of 5
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to George Town (GCM)
10/10 Exceptional! (194 reviews)
This place is fantastic! The beach is just a few steps away, our villa was clean and modern and within walking distance of restaurants. Everyone was friendly and helpful. They went above and beyond to make our vacation a relaxing one. We will definitely be returning.

Reviewed on Jul 8, 2025

Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to George Town (GCM)
9.8/10 Exceptional! (852 reviews)
All the staff was very friendly

Reviewed on Aug 16, 2025

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 Deals

Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
60 Tanager Way, Seven Mile Beach, Grand Cayman
Fully refundable
The price is ￥61,967 per night from Sep 13 to Sep 14
￥61,967
￥89,970 total
Sep 13 - Sep 14
includes taxes & fees
9.8/10 Exceptional! (863 reviews)
"Excellent"

Reviewed on Aug 14, 2025

Kimpton Seafire Resort + Spa by IHG
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
389 West Bay Road, Po Box 30371, Seven Mile Beach, Grand Cayman
Fully refundableReserve now, pay when you stay
The price is ￥41,066 per night from Sep 7 to Sep 8
￥41,066
￥60,899 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"It was a great stay. The only thing we disliked was the breakfast option, there was no buffet option during the weekdays."

Reviewed on Aug 12, 2025

Grand Cayman Marriott Resort
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
Fully refundableReserve now, pay when you stay
The price is ￥85,223 per night from Aug 23 to Aug 24
￥85,223
￥119,543 total
Aug 23 - Aug 24
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Every thing was perfect"

Reviewed on Aug 12, 2025

The Ritz-Carlton, Grand Cayman
See all 1,511 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 ￥412,859, 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.

Discover the most popular places to visit in Cayman Islands

Departing

Port of Georgetown

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

Port of Georgetown
#LifeAtExpedia

Governor's Beach

If a restful vacation is part of your travel plans, Governor's Beach might be the perfect place to seek out during your trip to Seven Mile Beach. Stroll along the area's seaside, or simply savor its seafood restaurants.

Governor's Beach

Camana Bay

You can browse for the perfect souvenirs at Camana Bay during your visit to Seven Mile Beach. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.

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