Cayman Islands Adventure Vacations
Book a Hotel + Flight or Car together to unlock savings
Photo by Cayman Islands Department of Tourism
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Flight and Adventure hotel deals in Cayman Islands
Price found within the past 48 hours. Click for updated prices.
Shangri-La Boutique Bed & Breakfast
Price was CA $1,734, price is now CA $1,211 per person
CA $1,211
per person
May 30 - Jun 6
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to George Town (GCM)
9.8/10 Exceptional! (208 reviews)
Very safe. We had a great stay: Everything lovely, staff very friendly. A relaxing stay.
Reviewed on Mar 18, 2026
Kimpton Seafire Resort + Spa by IHG
Price was CA $18,708, price is now CA $15,654 per person
CA $15,654
per person
May 30 - Jun 6
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to George Town (GCM)
9.8/10 Exceptional! (997 reviews)
Staff friendly. Hotel clean. Only draw back is beach staff for water sports and rental. Very rude and arrogant. Not the type that make you want to do any booking or activity with them
Reviewed on Mar 25, 2026
Regal Beach Club
Price was CA $2,553, price is now CA $2,287 per person
CA $2,287
per person
May 30 - Jun 6
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to George Town (GCM)
9.6/10 Exceptional! (311 reviews)
The beach an location are amazing! Parking our rental car was a breeze and we always had a spot. The condo was more than expected and wonderful!
Reviewed on Mar 28, 2026
The Sunshine Hotel and Suites
Price was CA $2,184, price is now CA $2,007 per person
CA $2,007
per person
May 30 - Jun 6
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to George Town (GCM)
9/10 Wonderful! (1,006 reviews)
Wonderful 2nd stay. Clean rooms, nice new pool, and friendly front desk staff. Disappointed the restaurant wasn’t open but will be visiting again.
Reviewed on Mar 28, 2026
Don't see what you're looking for?
See all available trips from Columbus to Cayman Islands
View all trips5* Adventure holidays in Cayman Islands
Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Grand Cayman
Price was CA $5,152, price is now CA $5,152 per person
CA $5,152
per person
May 30 - Jun 6
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to George Town (GCM)
9.6/10 Exceptional! (1,007 reviews)
The hospitality of the entire staff really stands out. The kids also really enjoyed the quest to find staff members from all over the world. All the restaurants were excellent, rooms clean and the pool and beach were well maintained and lots of fun.
Reviewed on Mar 28, 2026
Kimpton Seafire Resort + Spa by IHG
Price was CA $18,708, price is now CA $15,654 per person
CA $15,654
per person
May 30 - Jun 6
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to George Town (GCM)
9.8/10 Exceptional! (997 reviews)
Staff friendly. Hotel clean. Only draw back is beach staff for water sports and rental. Very rude and arrogant. Not the type that make you want to do any booking or activity with them
Reviewed on Mar 25, 2026
Don't see what you're looking for?
See all available trips from Columbus to Cayman Islands
View all trips3 Night Adventure holidays in Cayman Islands
Price found within the past 48 hours. Click for updated prices.
Shangri-La Boutique Bed & Breakfast
Price was CA $1,991, price is now CA $1,771 per person
CA $1,771
per person
Jun 4 - Jun 7
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to George Town (GCM)
9.8/10 Exceptional! (208 reviews)
Very safe. We had a great stay: Everything lovely, staff very friendly. A relaxing stay.
Reviewed on Mar 18, 2026
Kimpton Seafire Resort + Spa by IHG
Price was CA $9,368, price is now CA $8,464 per person
CA $8,464
per person
Jun 4 - Jun 7
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to George Town (GCM)
9.8/10 Exceptional! (997 reviews)
Staff friendly. Hotel clean. Only draw back is beach staff for water sports and rental. Very rude and arrogant. Not the type that make you want to do any booking or activity with them
Reviewed on Mar 25, 2026
Don't see what you're looking for?
See all available trips from Columbus to Cayman Islands
View all trips4 Night Adventure holidays in Cayman Islands
Price found within the past 48 hours. Click for updated prices.
Wyndham Reef Resort Grand Cayman
Price was CA $1,679, price is now CA $984 per person
CA $984
per person
Jun 2 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to George Town (GCM)
8.4/10 Very Good! (1,041 reviews)
Staff were very friendly. Our room was sparkling clean. Having a supermarket, restaurant, and a liquor store across the resort was a big plus.
Reviewed on Mar 19, 2026
Aqua Bay Club Condos
Price was CA $2,630, price is now CA $2,014 per person
CA $2,014
per person
Jun 2 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to George Town (GCM)
9.8/10 Exceptional! (90 reviews)
We stayed on the end condo on the ground floor. It was very clean and well stocked with comfy furnishings and amazing views! Claudette was so kind and helpful in the office along with the other girl. We sat in the screened in porch and watched the ocean and was able to snorkel right outside our condo. We will certainly stay again! The only minor negative was that the West end is pretty far away from restaurants and shopping so we took the public bus for those things.
Reviewed on Mar 1, 2026
Don't see what you're looking for?
See all available trips from Columbus to Cayman Islands
View all tripsAdventure Hotels in Cayman Islands
Wyndham Reef Resort Grand Cayman
2221 Queens Highway East End Grand Cayman
Book a stay at this beach condo in East End. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (1,047 reviews)
Everything you need
Reviewed on Mar 27, 2026
Grand Cayman Marriott Resort
389 West Bay Road Seven Mile Beach Grand Cayman
The price is CA $828 per night from Apr 27 to Apr 28
CA $828
CA $1,125 total
Apr 27 - Apr 28
includes taxes & 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! (1,007 reviews)
Everything was great … will do it again
Reviewed on Mar 28, 2026
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way Seven Mile Beach Grand Cayman
The price is CA $1,096 per night from Apr 12 to Apr 13
CA $1,096
CA $1,502 total
Apr 12 - Apr 13
includes taxes & 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)
Staff friendly. Hotel clean. Only draw back is beach staff for water sports and rental. Very rude and arrogant. Not the type that make you want to do any booking or activity with them
Reviewed on Mar 25, 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.