Luxury Vacations in Cayman Islands 2026

Photo by Cayman Islands Department of Tourism

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Flight and Luxury hotel deals in Cayman Islands

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

The Sunshine Hotel and Suites

CA $830

per person

Oct 24 - Oct 27

found 12 hours ago

Roundtrip flight included

Toronto (YTO) to George Town (GCM)

9/10 Wonderful! (1,007 reviews)

Kimpton Seafire Resort + Spa by IHG

Save 100% on your flight

CA $1,555

per person

Oct 24 - Oct 27

found 9 hours ago

Roundtrip flight included

Toronto (YTO) to George Town (GCM)

9.8/10 Exceptional! (1,005 reviews)

Amazing resort, amenities, cleanliness, service was top notch, the only thing that we didn’t like was the space in between chairs at the beach it felt like elbow to elbow with other people, still is a place that we will be back and will be highly recommended. Beautiful beach and resort!

Reviewed on Sep 23, 2026

Grand Cayman Marriott Beach Resort.

CA $1,030

per person

Oct 24 - Oct 27

found 12 hours ago

Roundtrip flight included

Toronto (YTO) to George Town (GCM)

9/10 Wonderful! (1,003 reviews)

Beach was closed during our stay but there wasn’t anyone working on the beach.

Reviewed on Sep 22, 2026

The Westin Grand Cayman Seven Mile Beach Resort & Spa

CA $1,238

per person

Oct 24 - Oct 27

found 12 hours ago

Roundtrip flight included

Toronto (YTO) to George Town (GCM)

9.2/10 Wonderful! (1,009 reviews)

Very nice resort just supper expensive but it was nice for the prices they have they should’ve at least include breakfast because everything its so expensive

Reviewed on Sep 23, 2026

The Ritz-Carlton, Grand Cayman

CA $1,599

per person

Oct 24 - Oct 27

found 12 hours ago

Roundtrip flight included

Toronto (YTO) to George Town (GCM)

9.6/10 Exceptional! (1,000 reviews)

This is what a vacation is supposed to be like. The property was beautiful and well maintained. The staff was superb and always dedicated to providing the best of the best service you can receive. The food was also excellent. With almost all food needing to be imported you will pay a great deal for each meal. However, when you take into account the amount of care, preparation, presentation, and execution they put into each food service you see exactly why you are happy to pay for an exceptional dining experience. Hat's off to this resort and staff. By the way, this was my 8 year olds first trip out of the country and he now wants to live at the Ritz.

Reviewed on Sep 22, 2026

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5* Luxury holidays in Cayman Islands

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

Kimpton Seafire Resort + Spa by IHG

Save 100% on your flight

CA $1,555

per person

Oct 24 - Oct 27

found 9 hours ago

Roundtrip flight included

Toronto (YTO) to George Town (GCM)

9.8/10 Exceptional! (1,005 reviews)

Reviewed on Sep 23, 2026

The Ritz-Carlton, Grand Cayman

CA $1,599

per person

Oct 24 - Oct 27

found 12 hours ago

Roundtrip flight included

Toronto (YTO) to George Town (GCM)

9.6/10 Exceptional! (1,000 reviews)

Reviewed on Sep 22, 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 holidays in Cayman Islands

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

The Sunshine Hotel and Suites

CA $830

per person

Oct 24 - Oct 27

found 12 hours ago

Roundtrip flight included

Toronto (YTO) to George Town (GCM)

9/10 Wonderful! (1,007 reviews)

Kimpton Seafire Resort + Spa by IHG

Save 100% on your flight

CA $1,555

per person

Oct 24 - Oct 27

found 9 hours ago

Roundtrip flight included

Toronto (YTO) to George Town (GCM)

9.8/10 Exceptional! (1,005 reviews)

Reviewed on Sep 23, 2026

Grand Cayman Marriott Beach Resort.

CA $1,030

per person

Oct 24 - Oct 27

found 12 hours ago

Roundtrip flight included

Toronto (YTO) to George Town (GCM)

9/10 Wonderful! (1,003 reviews)

Beach was closed during our stay but there wasn’t anyone working on the beach.

Reviewed on Sep 22, 2026

Don't see what you're looking for?

See all available trips from Columbus to Cayman Islands

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4 Night Luxury holidays 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

CA $888

per person

Oct 25 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to George Town (GCM)

8.4/10 Very good! (1,091 reviews)

The Westin Grand Cayman Seven Mile Beach Resort & Spa

Save 100% on your flight

CA $1,279

per person

Oct 25 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to George Town (GCM)

9.2/10 Wonderful! (1,009 reviews)

Very nice resort just supper expensive but it was nice for the prices they have they should’ve at least include breakfast because everything its so expensive

Reviewed on Sep 23, 2026

Kimpton Seafire Resort + Spa by IHG

CA $1,858

per person

Oct 25 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to George Town (GCM)

9.8/10 Exceptional! (1,005 reviews)

Reviewed on Sep 23, 2026

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What are some benefits when booking luxury Cayman Islands vacations?

When you book a luxury Cayman Islands vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

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

If you're looking for something luxurious in Cayman Islands, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $830, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 10. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Cayman Islands. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Cayman Islands?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Cayman Islands.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Cayman Islands. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Cayman Islands?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Cayman Islands or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Cayman Islands. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

Luxury Hotels in Cayman Islands

The Ritz-Carlton, Grand Cayman

West Bay Road Seven Mile Beach Grand Cayman

17 min walk from Seven Mile Beach

CA $855

CA $1,206 total

Sep 26 - Sep 27

includes taxes & fees

Book a stay at this luxury resort in Seven Mile Beach. Enjoy free WiFi, free valet parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. ...

9.6/10 Exceptional! (1,000 reviews)

"This is what a vacation is supposed to be like. The property was beautiful and well maintained. The staff was superb and always dedicated to providing the best of the best service you can receive. The food was also excellent. With almost all food needing to be imported you will pay a great deal for ..."

Reviewed on Sep 22, 2026

Caribbean Club Luxury Condo Hotel

871 West Bay Road Seven Mile Beach Grand Cayman

23 min walk from Seven Mile Beach

Book a stay at this luxury aparthotel in Seven Mile Beach. Enjoy free WiFi, a beach locale, and room service. Popular attractions Seven Mile Beach and Port of ...

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

Book a stay at this luxury hotel in West End. Enjoy private pools, a private beach, and a free beach shuttle. Popular attractions MV Captain Keith Tibbetts Shipwreck ...

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 1,552 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.