Grand Cayman Luxury Vacations 2026

Photo by Cayman Islands Department of Tourism

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Top Luxury vacation packages in Grand Cayman

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

The Sunshine Hotel and Suites

$1,154

per person

Nov 25 - Nov 28

found 15 hours ago

Roundtrip non-stop flight included

Baltimore (BWI) to George Town (GCM)

9/10 Wonderful! (1,001 reviews)

We loved our clean, comfortable and modern room. It had all the amenities we needed. We pared directly in front of our room. Staff were amazing and helpful.

Reviewed on Oct 23, 2026

The Ritz-Carlton, Grand Cayman

Save 100% on your flight

$2,465

per person

Nov 25 - Nov 28

found 15 hours ago

Roundtrip non-stop flight included

Baltimore (BWI) to George Town (GCM)

9.6/10 Exceptional! (1,013 reviews)

The Westin Grand Cayman Seven Mile Beach Resort & Spa

$1,906

per person

Nov 25 - Nov 28

found 15 hours ago

Roundtrip non-stop flight included

Baltimore (BWI) to George Town (GCM)

9.2/10 Wonderful! (1,003 reviews)

Excellent hotel

Reviewed on Oct 23, 2026

Kimpton Seafire Resort + Spa by IHG

Save 100% on your flight

$9,966

per person

Dec 26 - Jan 1

found 24 hours ago

Roundtrip flight included

Charlotte (CLT) to George Town (GCM)

9.8/10 Exceptional! (1,004 reviews)

The best stay ever

Reviewed on Oct 26, 2026

Grand Cayman Marriott Beach Resort

$3,917

per person

Dec 26 - Dec 29

found 19 hours ago

Roundtrip flight included

Baltimore (BWI) to George Town (GCM)

9/10 Wonderful! (1,001 reviews)

Great location and easy to get to from airport. Loved the beach and pool area. The attendants were very helpful with making sure you had umbrellas if you wanted shade. We ate at the pool/beach grill for an early dinner and that was very good as well. I thought food and drinks were on the expensive side but comparable for Grand cayman. We like to stay on 7-mile beach on arrival for a day or so before heading up to the East end. I gave a good rating instead of excellent because the rooms and elevator areas were dated and need upgrading.

Reviewed on Oct 26, 2026

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5* Luxury vacations in Grand Cayman

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

The Ritz-Carlton, Grand Cayman

Save 100% on your flight

$2,465

per person

Nov 25 - Nov 28

found 15 hours ago

Roundtrip non-stop flight included

Baltimore (BWI) to George Town (GCM)

9.6/10 Exceptional! (1,013 reviews)

Kimpton Seafire Resort + Spa by IHG

Save 100% on your flight

$9,966

per person

Dec 26 - Jan 1

found 24 hours ago

Roundtrip flight included

Charlotte (CLT) to George Town (GCM)

9.8/10 Exceptional! (1,004 reviews)

The best stay ever

Reviewed on Oct 26, 2026

Caribbean Club Luxury Condo Hotel

Save 100% on your flight

$14,770

per person

Dec 19 - Dec 26

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) 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

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3 Night Luxury vacations in Grand Cayman

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

The Westin Grand Cayman Seven Mile Beach Resort & Spa

$1,906

per person

Nov 25 - Nov 28

found 15 hours ago

Roundtrip non-stop flight included

Baltimore (BWI) to George Town (GCM)

9.2/10 Wonderful! (1,003 reviews)

Excellent hotel

Reviewed on Oct 23, 2026

The Ritz-Carlton, Grand Cayman

Save 100% on your flight

$2,465

per person

Nov 25 - Nov 28

found 15 hours ago

Roundtrip non-stop flight included

Baltimore (BWI) to George Town (GCM)

9.6/10 Exceptional! (1,013 reviews)

Kimpton Seafire Resort + Spa by IHG

$5,391

per person

Dec 30 - Jan 2

found 21 hours ago

Roundtrip non-stop flight included

Des Moines (DSM) to George Town (GCM)

9.8/10 Exceptional! (1,004 reviews)

The best stay ever

Reviewed on Oct 26, 2026

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4 Night Luxury vacations in Grand Cayman

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

The Reef Beach Resort, East End, Grand Cayman

Save 100% on your flight

$947

per person

Nov 30 - Dec 4

found 1 day ago

Roundtrip flight included

New York (JFK) to George Town (GCM)

8.4/10 Very Good! (1,101 reviews)

Loved the walkout except at night when sound travelled into the unit from the pool, adjoining decks like they were in the building. Linens could be improved….old, poor quality. Great people/staff. Stay here often because of them.

Reviewed on Oct 26, 2026

The Ritz-Carlton, Grand Cayman

$3,131

per person

Nov 25 - Nov 29

found 17 hours ago

Roundtrip non-stop flight included

Columbus (CMH) to George Town (GCM)

9.6/10 Exceptional! (1,013 reviews)

The Westin Grand Cayman Seven Mile Beach Resort & Spa

$2,435

per person

Nov 25 - Nov 29

found 17 hours ago

Roundtrip non-stop flight included

Columbus (CMH) to George Town (GCM)

9.2/10 Wonderful! (1,003 reviews)

Excellent hotel

Reviewed on Oct 23, 2026

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What can I expect from a luxury Grand Cayman vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Grand Cayman 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 Grand Cayman?

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 Grand Cayman 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 $947. Prices and availability are subject to change. Additional terms may apply.

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

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 Grand Cayman 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 Grand Cayman?

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 Grand Cayman 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 Grand Cayman 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 Grand Cayman Hotels

The Ritz-Carlton, Grand Cayman

West Bay Road Seven Mile Beach Grand Cayman

23 min drive from Grand Cayman Beaches

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 ...

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

The Sunshine Hotel and Suites

1465 Esterley Tibbetts Seven Mile Beach Grand Cayman

23 min drive from Grand Cayman Beaches

The Sunshine Hotel and Suites is one of the Seven Mile Beach luxury 4-star beach properties where you can pamper yourself with pillowtop beds, premium channels, ...

9/10 Wonderful! (1,001 reviews)

"We loved our clean, comfortable and modern room. It had all the amenities we needed. We pared directly in front of our room. Staff were amazing and helpful."

Reviewed on Oct 23, 2026

See all 1,471 properties in Grand Cayman

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.