Cayman Islands Adventure Vacations
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Photo by Cayman Islands Department of Tourism
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Top Adventure vacation packages in Cayman Islands
Price found within the past 48 hours. Click for updated prices.
Shangri-La Boutique Bed & Breakfast
Price was $909, price is now $812 per person
$812
per person
Jun 29 - Jul 2
found 20 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to George Town (GCM)
9.8/10 Exceptional! (210 reviews)
Often photos of a destination do not tell the "whole story." These accomodations were even more stunning than the photos make it out to be. Staff are incredibly attentive to guest needs. The resort has supplies for day trips to the beach, saving the guest from having to pre plan these items, beach bags, big floppy sun hats, fins, masks, snorkels, chairs, umbrellas, beach towels etc. The staff, Rose in particular offered spectacular suggestions for dining and sight seeing. We spent mornings having coffee and watching the wildlife. After long days out and about relaxing in the pool and hot tub was wonderful. There was not a single issue we encountered and this resort was an excellent choice.
Reviewed on Apr 22, 2026
Ocean Paradise
Price was $1,537, price is now $1,265 per person
$1,265
per person
Jun 29 - Jul 2
found 20 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to George Town (GCM)
9.6/10 Exceptional! (39 reviews)
This is very njce place to stay. Very calm and clean property.
It is just 45 minutes away from main town but great place to stay.
Reviewed on Apr 1, 2026
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Price was $2,100, price is now $1,863 per person
$1,863
per person
May 29 - May 31
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to George Town (GCM)
9.2/10 Wonderful! (1,003 reviews)
The rooms were clean, the staff was friendly and helpful. Linton from the beach staff was exceptional. I am looking forward to going back again.
Reviewed on Apr 28, 2026
Kimpton Seafire Resort + Spa by IHG
Price was $2,421, price is now $2,175 per person
$2,175
per person
Jun 29 - Jul 3
found 9 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to George Town (GCM)
9.8/10 Exceptional! (1,000 reviews)
The offer of another room after check out was appreciated to bridge the gap between checkout at airport , but the denial of spa facilities such as a team room and sauna unless I ponied up for “services” was inexplicable given that i was paying £1500 per night!
Reviewed on Apr 22, 2026
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View all trips5* Adventure vacations in Cayman Islands
Price found within the past 48 hours. Click for updated prices.
Kimpton Seafire Resort + Spa by IHG
Price was $2,421, price is now $2,175 per person
$2,175
per person
Jun 29 - Jul 3
found 9 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to George Town (GCM)
9.8/10 Exceptional! (1,000 reviews)
The offer of another room after check out was appreciated to bridge the gap between checkout at airport , but the denial of spa facilities such as a team room and sauna unless I ponied up for “services” was inexplicable given that i was paying £1500 per night!
Reviewed on Apr 22, 2026
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View all trips3 Night Adventure vacations in Cayman Islands
Price found within the past 48 hours. Click for updated prices.
Shangri-La Boutique Bed & Breakfast
Price was $1,025, price is now $855 per person
$855
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Detroit (DTT) to George Town (GCM)
9.8/10 Exceptional! (210 reviews)
Often photos of a destination do not tell the "whole story." These accomodations were even more stunning than the photos make it out to be. Staff are incredibly attentive to guest needs. The resort has supplies for day trips to the beach, saving the guest from having to pre plan these items, beach bags, big floppy sun hats, fins, masks, snorkels, chairs, umbrellas, beach towels etc. The staff, Rose in particular offered spectacular suggestions for dining and sight seeing. We spent mornings having coffee and watching the wildlife. After long days out and about relaxing in the pool and hot tub was wonderful. There was not a single issue we encountered and this resort was an excellent choice.
Reviewed on Apr 22, 2026
Ocean Paradise
Price was $1,471, price is now $1,145 per person
$1,145
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Detroit (DTT) to George Town (GCM)
9.6/10 Exceptional! (39 reviews)
This is very njce place to stay. Very calm and clean property.
It is just 45 minutes away from main town but great place to stay.
Reviewed on Apr 1, 2026
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Price was $2,640, price is now $2,116 per person
$2,116
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Detroit (DTT) to George Town (GCM)
9.2/10 Wonderful! (1,003 reviews)
The rooms were clean, the staff was friendly and helpful. Linton from the beach staff was exceptional. I am looking forward to going back again.
Reviewed on Apr 28, 2026
Don't see what you're looking for?
See all available trips from Columbus to Cayman Islands
View all trips4 Night Adventure vacations in Cayman Islands
Price found within the past 48 hours. Click for updated prices.
Shangri-La Boutique Bed & Breakfast
Price was $889, price is now $667 per person
$667
per person
May 30 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to George Town (GCM)
9.8/10 Exceptional! (210 reviews)
Often photos of a destination do not tell the "whole story." These accomodations were even more stunning than the photos make it out to be. Staff are incredibly attentive to guest needs. The resort has supplies for day trips to the beach, saving the guest from having to pre plan these items, beach bags, big floppy sun hats, fins, masks, snorkels, chairs, umbrellas, beach towels etc. The staff, Rose in particular offered spectacular suggestions for dining and sight seeing. We spent mornings having coffee and watching the wildlife. After long days out and about relaxing in the pool and hot tub was wonderful. There was not a single issue we encountered and this resort was an excellent choice.
Reviewed on Apr 22, 2026
Ocean Paradise
Price was $1,564, price is now $1,052 per person
$1,052
per person
May 30 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to George Town (GCM)
9.6/10 Exceptional! (39 reviews)
This is very njce place to stay. Very calm and clean property.
It is just 45 minutes away from main town but great place to stay.
Reviewed on Apr 1, 2026
The Reef Beach Resort, East End, Grand Cayman
Price was $1,439, price is now $1,040 per person
$1,040
per person
Jun 29 - Jul 3
found 9 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to George Town (GCM)
8.4/10 Very Good! (1,053 reviews)
The Reef Resort was outstanding. The property was clean, and the customer service was exceptional. The grounds and pools were easy to access, making it simple to relax and enjoy every part of the resort. The beach felt like our backyard—just steps away—with a beautiful coastline that added to the peaceful atmosphere. There was great entertainment and delicious food throughout our stay. Overall, it was a relaxing, enjoyable experience that I would definitely recommend.
Reviewed on Apr 22, 2026
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View all tripsFind awesome Cayman Islands adventure vacations
How can I book the best Cayman Islands adventure trips?
Choose your own adventure in Cayman Islands, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.
How can I plan the perfect Cayman Islands family adventure vacation?
Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Cayman Islands. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.
Can I book all-inclusive Cayman Islands adventure vacation packages?
By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.
Why should I book a Cayman Islands adventure vacation for couples?
Book a Cayman Islands couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.
How can I find the best deals on adventure packages in Cayman Islands?
It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.
Can I book an adventure vacation package in Cayman Islands with free cancellation and/or flexible dates?
Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.
Why should I book a Cayman Islands adventure trip with Expedia?
Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.
Top Adventure Cayman Islands Hotels
The Reef Beach Resort, East End, Grand Cayman
2221 Queens Highway East End Grand Cayman
Book a stay at this beach aparthotel in East End. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very Good! (1,055 reviews)
Room was fantastic! Quiet area, but activities provided for those who wanted. Far from attractions but really great for a low key vacation. View from my room was amazing - so relaxing! Beach was a bit rough but I saw lots of people enjoying snorkelling. I made use of the spa and gym, and enjoyed ...
Reviewed on Apr 28, 2026
Grand Cayman Marriott Resort
389 West Bay Road Seven Mile Beach Grand Cayman
$491 nightly
The price is $549 total per night from May 21 to May 22
$549 total
May 21 - May 22
Total with taxes and fees
Book a stay at this luxury resort in Seven Mile Beach. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the ...
9/10 Wonderful! (1,001 reviews)
Poolside sitting is very comfortable, stuff is very good
Reviewed on Apr 28, 2026
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way Seven Mile Beach Grand Cayman
$1,046 nightly
The price is $1,169 total per night from May 8 to May 9
$1,169 total
May 8 - May 9
Total with taxes and fees
Book a stay at this luxury hotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ...
9.8/10 Exceptional! (1,000 reviews)
The offer of another room after check out was appreciated to bridge the gap between checkout at airport , but the denial of spa facilities such as a team room and sauna unless I ponied up for “services” was inexplicable given that i was paying £1500 per night!
Reviewed on Apr 22, 2026
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.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
