Cayman Islands Luxury Vacations 2026

Photo by Cayman Islands Department of Tourism

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Top Luxury vacation packages in Cayman Islands

Price found within the past 48 hours. Click for updated prices.

The Sunshine Hotel and Suites

$1,129

per person

Dec 18 - Dec 20

found 1 day ago

Roundtrip flight included

Chicago (CHI) to George Town (GCM)

9/10 Wonderful! (1,005 reviews)

Clean room. Get bed. Bathroom was clean.

Reviewed on Oct 12, 2026

The Ritz-Carlton, Grand Cayman

$1,557

per person

Dec 18 - Dec 20

found 1 day ago

Roundtrip flight included

Chicago (CHI) to George Town (GCM)

9.6/10 Exceptional! (1,004 reviews)

I thoroughly enjoyed my stay here. The property and service are flawless. I could not have been looked after better.

Reviewed on Oct 18, 2026

Kimpton Seafire Resort + Spa by IHG

Save 100% on your flight

$2,095

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to George Town (GCM)

9.8/10 Exceptional! (1,005 reviews)

Caribbean Club Luxury Condo Hotel

Save 100% on your flight

$9,546

per person

Nov 22 - Nov 27

found 7 hours ago

Roundtrip non-stop flight included

Chicago (CHI) to George Town (GCM)

9.8/10 Exceptional! (45 reviews)

Excellent Property. Their front desk team needs some working on because they give couldn't care less attitude.

Reviewed on Feb 25, 2024

Grand Cayman Marriott Beach Resort

$1,439

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to George Town (GCM)

9/10 Wonderful! (1,003 reviews)

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5* Luxury vacations in Cayman Islands

Price found within the past 48 hours. Click for updated prices.

The Ritz-Carlton, Grand Cayman

$1,557

per person

Dec 18 - Dec 20

found 1 day ago

Roundtrip flight included

Chicago (CHI) to George Town (GCM)

9.6/10 Exceptional! (1,004 reviews)

I thoroughly enjoyed my stay here. The property and service are flawless. I could not have been looked after better.

Reviewed on Oct 18, 2026

Kimpton Seafire Resort + Spa by IHG

Save 100% on your flight

$2,095

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to George Town (GCM)

9.8/10 Exceptional! (1,005 reviews)

Caribbean Club Luxury Condo Hotel

Save 100% on your flight

$9,546

per person

Nov 22 - Nov 27

found 7 hours ago

Roundtrip non-stop flight included

Chicago (CHI) to George Town (GCM)

9.8/10 Exceptional! (45 reviews)

Excellent Property. Their front desk team needs some working on because they give couldn't care less attitude.

Reviewed on Feb 25, 2024

Don't see what you're looking for?

See all available trips from Columbus to Cayman Islands

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3 Night Luxury vacations in Cayman Islands

Price found within the past 48 hours. Click for updated prices.

The Sunshine Hotel and Suites

$1,088

per person

Dec 21 - Dec 24

found 6 hours ago

Roundtrip non-stop flight included

Austin (AUS) to George Town (GCM)

9/10 Wonderful! (1,005 reviews)

Clean room. Get bed. Bathroom was clean.

Reviewed on Oct 12, 2026

Kimpton Seafire Resort + Spa by IHG

Save 100% on your flight

$3,550

per person

Dec 21 - Dec 24

found 6 hours ago

Roundtrip non-stop flight included

Austin (AUS) to George Town (GCM)

9.8/10 Exceptional! (1,005 reviews)

Grand Cayman Marriott Beach Resort

$2,244

per person

Dec 21 - Dec 24

found 6 hours ago

Roundtrip non-stop flight included

Austin (AUS) to George Town (GCM)

9/10 Wonderful! (1,003 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Cayman Islands

View all trips

4 Night Luxury vacations in Cayman Islands

Price found within the past 48 hours. Click for updated prices.

The Reef Beach Resort, East End, Grand Cayman

Save 100% on your flight

$644

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to George Town (GCM)

8.4/10 Very Good! (1,098 reviews)

Tho no fault of the resort, I wish I was made aware of the Sargassum (bad egg smelling seaweed)

Reviewed on Oct 15, 2026

The Sunshine Hotel and Suites

$1,498

per person

Dec 18 - Dec 22

found 1 day ago

Roundtrip flight included

Washington (WAS) to George Town (GCM)

9/10 Wonderful! (1,005 reviews)

Clean room. Get bed. Bathroom was clean.

Reviewed on Oct 12, 2026

Kimpton Seafire Resort + Spa by IHG

Save 100% on your flight

$5,069

per person

Dec 18 - Dec 22

found 1 day ago

Roundtrip flight included

Washington (WAS) to George Town (GCM)

9.8/10 Exceptional! (1,005 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Cayman Islands

View all trips

What can I expect from a luxury Cayman Islands vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Cayman Islands vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Cayman Islands?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Cayman Islands luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $644. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Cayman Islands?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Cayman Islands with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Cayman Islands?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Cayman Islands with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Cayman Islands with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.

Top Luxury Cayman Islands Hotels

The Ritz-Carlton, Grand Cayman

West Bay Road Seven Mile Beach Grand Cayman

23 min drive from Grand Cayman Beaches

$913 nightly

$1,033 total

Oct 19 - Oct 20

Total with taxes and fees

The Ritz-Carlton, Grand Cayman is one of the Seven Mile Beach grand 5-star beach properties where you can pamper yourself with deep soaking bathtubs and Champagne ...

9.6/10 Exceptional! (1,011 reviews)

"I thoroughly enjoyed my stay here. The property and service are flawless. I could not have been looked after better."

Reviewed on Oct 18, 2026

Caribbean Club Luxury Condo Hotel

871 West Bay Road Seven Mile Beach Grand Cayman

23 min drive from Grand Cayman Beaches

Caribbean Club Luxury Condo Hotel is a sumptuous 5-star beach property where you can be treated to jetted bathtubs and premium bedding. Notable amenities include ...

9.8/10 Exceptional! (45 reviews)

"Excellent Property. Their front desk team needs some working on because they give couldn't care less attitude."

Reviewed on Feb 25, 2024

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Le Soleil d'Or

2147 South Side Road West End Cayman Brac

3 hours drive from Grand Cayman Beaches

Le Soleil d'Or is a sumptuous 5-star beach property where you can treat yourself to private pools and Frette Italian sheets. The private beach, outdoor tennis ...

10/10 Exceptional! (7 reviews)

Fantastic Property

"Staff were unreal and the cottage was amazing"

Reviewed on Jul 24, 2019

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See all 1,545 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.