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.
Cayman Luxury Rentals at Ocean Paradise
$870
per person
Oct 29 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
9.8/10 Exceptional! (43 reviews)
Family friendly, very equipped accommodation. Caring and quick responsive staff. Would definitely recommend the place.
Reviewed on Jul 11, 2026
Regal Beach Club
$1,213
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
9.6/10 Exceptional! (353 reviews)
I loved how close to the pool our unit was. I purposely booked a ground floor so we wouldn't have to drag luggage up steps because there is no elevator. Not a wide beach but I like that. Easy to get to the water and it was usually so calm. The condo was perfect for our needs. We mostly ate at the condo. We grilled out one night and cooked breakfast in the mornings. It was Labor Day weekend, low season, and there was hardly anyone there! We plan to return to this condo for a longer vacation sometime. I would highly recommend this condo.
Reviewed on Sep 10, 2026
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View all trips5* Adventure vacations in Cayman Islands
Price found within the past 48 hours. Click for updated prices.
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View all trips3 Night Adventure vacations in Cayman Islands
Price found within the past 48 hours. Click for updated prices.
Cayman Luxury Rentals at Ocean Paradise
$992
per person
Oct 30 - Nov 2
found 2 hours ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (43 reviews)
Family friendly, very equipped accommodation. Caring and quick responsive staff. Would definitely recommend the place.
Reviewed on Jul 11, 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 Westin Grand Cayman Seven Mile Beach Resort & Spa
$1,216
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
9.2/10 Wonderful! (1,005 reviews)
The hotel is beautiful and the beds were so comfortable. The staff was super friendly and helpful, especially the front doorman. It was raining for 2 days and as we were walking back to our room he would do a dance to stop the rain, believe it or not it seemed to work lol. Plenty of things to do the food was great. The front desk remembered that we said it was our anniversary when we checked in and suprised us with a bottle of wine and chocolate covered strawberries. It was so nice! There is also a restaurant across the street called Legendz it was delicious and much cheaper. The only disappointment was everytime I tried to order room service it wasn't available. other than that we would definitely recommend the Westin and will be back.
Reviewed on Sep 29, 2026
Cayman Luxury Rentals at Ocean Paradise
$966
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
9.8/10 Exceptional! (43 reviews)
Family friendly, very equipped accommodation. Caring and quick responsive staff. Would definitely recommend the place.
Reviewed on Jul 11, 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
- 20 min drive from Grand Cayman Beaches
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! (1,098 reviews)
"Clean room, beach view excellent staff"
Reviewed on Sep 27, 2026
Grand Cayman Marriott Beach Resort
389 West Bay Road Seven Mile Beach Grand Cayman
- 24 min drive from Grand Cayman Beaches
$433 nightly
$489 total
Oct 15 - Oct 16
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 ...
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way Seven Mile Beach Grand Cayman
- 24 min drive from Grand Cayman Beaches
$565 nightly
$631 total
Sep 30 - Oct 1
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 ...
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
