Cayman Islands Adventure Vacations
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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 $964, price is now $800 per person
$800
per person
Jul 19 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to George Town (GCM)
9.8/10 Exceptional! (214 reviews)
The Shangri La is an absolute gem of a B&B. We selected it because we were looking for a quiet place far from the large hotels . What we actually found was a welcoming home, not just a functional accommodation. The facilities are great (hammock, pool, hot tub, beach towels etc). The rooms are very clean and comfortable, yet also private. The fully equipped kitchen is accessible at all hours, and breakfast on the deck is in a very peaceful setting. All these are important considerations in a relaxing place to stay . But what made the Shangri La truly memorable is the folks who run it. We have rarely had stays where we felt so genuinely welcome. Rose, who manages the operation, is especially accommodating. Our flight arrival was well before check in time, and we stopped by just in case our room was ready. It wasn’t, but we waited in the comfortable lounge and they made up the room very quickly. We would have been fine to just leave our bags and return later, but this way we were able to settle in and unpack. Throughout our stay, nothing was too much trouble for Rose, and we recommend the Shangri La very highly.
Reviewed on May 5, 2026
Ocean Paradise
Price was $1,467, price is now $1,091 per person
$1,091
per person
Jul 19 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) 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 $2,167, price is now $1,686 per person
$1,686
per person
Jul 19 - Jul 23
found 24 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to George Town (GCM)
9.2/10 Wonderful! (1,008 reviews)
Room was clean. Noticed a sewage smell coming from the toilet, the whole time we were there. Seems like for the price this hotel could use some renovations. Was promised that I would get an ocean view room the day after I checked in. I went to front desk to check the following morning, and they told me there were not any rooms with king beds available. Just a double queen bed and it would cost $100 more per day. I declined that due to already paying a lot for the room we got above the front door. The other thing I noticed is that if you want to relax or take a nap in the room during the day it is extremely noisy. Between talking loudly and all the doors slamming it was impossible to be in the room during the day. The best part of this hotel is the location. It is right on the beach, and they have plenty of beach loungers with umbrellas. This is my third time at The Westin in 10 years, the first year they were working on the lobby so that is pretty new and still in good shape.
Reviewed on May 18, 2026
The Sunshine Hotel and Suites
Price was $1,104, price is now $973 per person
$973
per person
Jul 19 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to George Town (GCM)
9/10 Wonderful! (1,009 reviews)
Everything and everyone was great! Very close restaurant close by, being able to use the Westin amenities was wonderful too! Definitely recommend!
Reviewed on May 18, 2026
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View all trips5* Adventure vacations in Cayman Islands
Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Grand Cayman
Price was $1,088, price is now $1,088 per person
$1,088
per person
Jun 18 - Jun 20
found 14 hours ago
Roundtrip non-stop flight included
New York (NYC) to George Town (GCM)
9.6/10 Exceptional! (1,004 reviews)
The only reason I didn't give them 5 Stars its because of the Beach Chairs. They are horrible
Reviewed on May 12, 2026
Kimpton Seafire Resort + Spa by IHG
Price was $2,304, price is now $2,115 per person
$2,115
per person
Jun 20 - Jun 23
found 18 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to George Town (GCM)
9.8/10 Exceptional! (1,000 reviews)
A truly impressive property and location on 7 mile beach. The staff from every aspect of the resort were so friendly, engaging, and personable. The restaurants were great, the beach is outstanding, and the view from the balcony was stunning. So happy we chose the Kimpton Seafire for our vacation and a very heartfelt thank you to all the staff and management of this beautiful property.
Reviewed on May 19, 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 $1,035, price is now $853 per person
$853
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Atlantic City (ACY) to George Town (GCM)
9.8/10 Exceptional! (214 reviews)
The Shangri La is an absolute gem of a B&B. We selected it because we were looking for a quiet place far from the large hotels . What we actually found was a welcoming home, not just a functional accommodation. The facilities are great (hammock, pool, hot tub, beach towels etc). The rooms are very clean and comfortable, yet also private. The fully equipped kitchen is accessible at all hours, and breakfast on the deck is in a very peaceful setting. All these are important considerations in a relaxing place to stay . But what made the Shangri La truly memorable is the folks who run it. We have rarely had stays where we felt so genuinely welcome. Rose, who manages the operation, is especially accommodating. Our flight arrival was well before check in time, and we stopped by just in case our room was ready. It wasn’t, but we waited in the comfortable lounge and they made up the room very quickly. We would have been fine to just leave our bags and return later, but this way we were able to settle in and unpack. Throughout our stay, nothing was too much trouble for Rose, and we recommend the Shangri La very highly.
Reviewed on May 5, 2026
Ocean Paradise
Price was $1,467, price is now $1,091 per person
$1,091
per person
Jul 19 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) 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 $1,900, price is now $1,672 per person
$1,672
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Atlantic City (ACY) to George Town (GCM)
9.2/10 Wonderful! (1,008 reviews)
Room was clean. Noticed a sewage smell coming from the toilet, the whole time we were there. Seems like for the price this hotel could use some renovations. Was promised that I would get an ocean view room the day after I checked in. I went to front desk to check the following morning, and they told me there were not any rooms with king beds available. Just a double queen bed and it would cost $100 more per day. I declined that due to already paying a lot for the room we got above the front door. The other thing I noticed is that if you want to relax or take a nap in the room during the day it is extremely noisy. Between talking loudly and all the doors slamming it was impossible to be in the room during the day. The best part of this hotel is the location. It is right on the beach, and they have plenty of beach loungers with umbrellas. This is my third time at The Westin in 10 years, the first year they were working on the lobby so that is pretty new and still in good shape.
Reviewed on May 18, 2026
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View all trips4 Night Adventure 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
Price was $1,284, price is now $769 per person
$769
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to George Town (GCM)
8.4/10 Very Good! (1,065 reviews)
Great Location Awesome Stay
Reviewed on May 14, 2026
Ocean Paradise
Save 100% on your flight
Price was $1,569, price is now $1,106 per person
$1,106
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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 $2,167, price is now $1,686 per person
$1,686
per person
Jul 19 - Jul 23
found 24 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to George Town (GCM)
9.2/10 Wonderful! (1,008 reviews)
Room was clean. Noticed a sewage smell coming from the toilet, the whole time we were there. Seems like for the price this hotel could use some renovations. Was promised that I would get an ocean view room the day after I checked in. I went to front desk to check the following morning, and they told me there were not any rooms with king beds available. Just a double queen bed and it would cost $100 more per day. I declined that due to already paying a lot for the room we got above the front door. The other thing I noticed is that if you want to relax or take a nap in the room during the day it is extremely noisy. Between talking loudly and all the doors slamming it was impossible to be in the room during the day. The best part of this hotel is the location. It is right on the beach, and they have plenty of beach loungers with umbrellas. This is my third time at The Westin in 10 years, the first year they were working on the lobby so that is pretty new and still in good shape.
Reviewed on May 18, 2026
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See all available trips from Columbus to Cayman Islands
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! (1,068 reviews)
"Great Location Awesome Stay"
Reviewed on May 14, 2026
Grand Cayman Marriott Resort
389 West Bay Road Seven Mile Beach Grand Cayman
$402 nightly
The price is $455 total per night from Jun 5 to Jun 6
$455 total
Jun 5 - Jun 6
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! (1,005 reviews)
"It was my first time in the Cayman Islands, and I overall enjoyed it. My boyfriend and I enjoyed staying at the Grand Cayman Marriott Resort. Our check-in and check-out process was smooth. It was my birthday, so my boyfriend had the room decorated, which was great. They also had a cake for me. The ..."
Reviewed on May 17, 2026
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way Seven Mile Beach Grand Cayman
$1,125 nightly
The price is $1,256 total per night from May 21 to May 22
$1,256 total
May 21 - May 22
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! (1,001 reviews)
"A truly impressive property and location on 7 mile beach. The staff from every aspect of the resort were so friendly, engaging, and personable. The restaurants were great, the beach is outstanding, and the view from the balcony was stunning. So happy we chose the Kimpton Seafire for our vacation ..."
Reviewed on May 19, 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.
