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

$1,077

per person

Oct 31 - Nov 4

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to George Town (GCM)

9/10 Wonderful! (1,006 reviews)

Kimpton Seafire Resort + Spa by IHG

$1,438

per person

Sep 30 - Oct 4

found 5 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to George Town (GCM)

9.8/10 Exceptional! (1,016 reviews)

This a must go to destination!!!!!!

Reviewed on Aug 31, 2026

The Westin Grand Cayman Seven Mile Beach Resort & Spa

$1,276

per person

Sep 30 - Oct 4

found 5 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to George Town (GCM)

9.2/10 Wonderful! (1,008 reviews)

Chairs on the beach is very close to each other and front row is impossible to get because people leave theire belongings on the chairs starting 5:30 am and go back to rooms and sometimes do not come back untill 10 or 11 am

Reviewed on Aug 30, 2026

Grand Cayman Marriott Resort

$1,091

per person

Sep 30 - Oct 4

found 5 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to George Town (GCM)

9/10 Wonderful! (1,004 reviews)

The Ritz-Carlton, Grand Cayman

$2,236

per person

Oct 31 - Nov 4

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to George Town (GCM)

9.6/10 Exceptional! (1,008 reviews)

Beach is Fantastic. Service is what you expect from Ritz. Very friendly staff too

Reviewed on Aug 29, 2026

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5* Luxury vacations in Cayman Islands

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

Kimpton Seafire Resort + Spa by IHG

$1,438

per person

Sep 30 - Oct 4

found 5 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to George Town (GCM)

9.8/10 Exceptional! (1,016 reviews)

This a must go to destination!!!!!!

Reviewed on Aug 31, 2026

The Ritz-Carlton, Grand Cayman

$2,236

per person

Oct 31 - Nov 4

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to George Town (GCM)

9.6/10 Exceptional! (1,008 reviews)

Beach is Fantastic. Service is what you expect from Ritz. Very friendly staff too

Reviewed on Aug 29, 2026

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.

Grand Cayman Marriott Resort

$704

per person

Oct 1 - Oct 4

found 22 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to George Town (GCM)

9/10 Wonderful! (1,004 reviews)

Kimpton Seafire Resort + Spa by IHG

$963

per person

Oct 1 - Oct 4

found 22 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to George Town (GCM)

9.8/10 Exceptional! (1,016 reviews)

This a must go to destination!!!!!!

Reviewed on Aug 31, 2026

The Sunshine Hotel and Suites

$873

per person

Nov 1 - Nov 4

found 12 hours ago

Roundtrip non-stop flight included

Norfolk (ORF) to George Town (GCM)

9/10 Wonderful! (1,006 reviews)

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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

$833

per person

Oct 31 - Nov 4

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to George Town (GCM)

8.4/10 Very Good! (1,090 reviews)

I enjoyed everything from the room to the pool to the restaurant they had different activities everynight and what I like most was that the staff was very helpful and accommodating.shout out to the staff from the restaurant that served us that amazing breakfast and was there to make us if it’s even a small drink when the bar was either not open as yet or closed.and the staff at the bar was amazing too ❤️the staff at reef was what made both me and my families stay amazing.definitely recommend and will be coming back soon.

Reviewed on Aug 29, 2026

Kimpton Seafire Resort + Spa by IHG

$1,438

per person

Sep 30 - Oct 4

found 5 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to George Town (GCM)

9.8/10 Exceptional! (1,016 reviews)

This a must go to destination!!!!!!

Reviewed on Aug 31, 2026

The Westin Grand Cayman Seven Mile Beach Resort & Spa

$1,276

per person

Sep 30 - Oct 4

found 5 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to George Town (GCM)

9.2/10 Wonderful! (1,008 reviews)

Reviewed on Aug 30, 2026

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See all available trips from Columbus to Cayman Islands

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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 $704. 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

17 min walk from Seven Mile Beach

$767 nightly

$859 total

Sep 7 - Sep 8

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! (1,005 reviews)

"Beach is Fantastic. Service is what you expect from Ritz. Very friendly staff too"

Reviewed on Aug 29, 2026

Caribbean Club Luxury Condo Hotel

871 West Bay Road Seven Mile Beach Grand Cayman

23 min walk from Seven Mile Beach

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 Seven Mile Beach

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 1,548 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.