Grand Cayman Romantic Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Cayman Islands Department of Tourism
- Plan, book, travel with confidence
Better together
Save up to €185 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Shangri-La Boutique Bed & Breakfast
Price was €1,036, price is now €832 per person
€832
per person
13 Nov - 20 Nov
found 18 hours ago
Return direct flight included
Hartford (BDL) to George Town (GCM)
9.8/10 Exceptional! (195 reviews)
We had a great stay at Shangri-La! The rooms were nice and comfortable, but what really stood out was the staff(especially Ms. Rose) they were super friendly, helpful, and went above and beyond to make us feel welcome. Would definitely come back once visiting the Cayman Islands!
Reviewed on 28 Sept 2025
Kimpton Seafire Resort + Spa by IHG
Save 100% on your flight
Price was €3,188, price is now €2,603 per person
€2,603
per person
13 Nov - 20 Nov
found 18 hours ago
Return direct flight included
Hartford (BDL) to George Town (GCM)
9.8/10 Exceptional! (894 reviews)
Everything about this property was absolutely phenomenal
Reviewed on 1 Oct 2025
Grand Cayman Marriott Resort
Price was €1,466, price is now €1,325 per person
€1,325
per person
13 Nov - 20 Nov
found 18 hours ago
Return direct flight included
Hartford (BDL) to George Town (GCM)
9/10 Wonderful! (1,006 reviews)
My husband and I stayed these last week for 5 days 4 nights and it was absolutely wonderful. The staff was amazing and they all gave top tier service….!!
Reviewed on 25 Sept 2025
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Price was €1,932, price is now €1,932 per person
€1,932
per person
13 Nov - 20 Nov
found 18 hours ago
Return direct flight included
Hartford (BDL) to George Town (GCM)
9/10 Wonderful! (1,009 reviews)
I loved visiting in September as it's the LOW season. The staff is so friendly and helpful, delightful.
The only negative is that the mattress could use an upgrade; it was too soft.
Reviewed on 21 Sept 2025
The Ritz-Carlton, Grand Cayman
Price was €2,945, price is now €2,945 per person
€2,945
per person
13 Nov - 20 Nov
found 18 hours ago
Return direct flight included
Hartford (BDL) to George Town (GCM)
9.6/10 Exceptional! (1,005 reviews)
Our stay at The Ritz Carlton - Grand Cayman was nothing short of spectacular. The hotel's elegant design, combined with its top-notch amenities, made for a truly relaxing and enjoyable experience. The staff went above and beyond to ensure my comfort and satisfaction. We can wait to be back again next year!
Reviewed on 1 Oct 2025
Don't see what you're looking for?
See all available trips from Hartford to Grand Cayman
View all tripsPrice found within the past 48 hours. Click for updated prices.
Kimpton Seafire Resort + Spa by IHG
Save 100% on your flight
Price was €3,188, price is now €2,603 per person
€2,603
per person
13 Nov - 20 Nov
found 18 hours ago
Return direct flight included
Hartford (BDL) to George Town (GCM)
9.8/10 Exceptional! (894 reviews)
Everything about this property was absolutely phenomenal
Reviewed on 1 Oct 2025
The Ritz-Carlton, Grand Cayman
Price was €2,945, price is now €2,945 per person
€2,945
per person
13 Nov - 20 Nov
found 18 hours ago
Return direct flight included
Hartford (BDL) to George Town (GCM)
9.6/10 Exceptional! (1,005 reviews)
Our stay at The Ritz Carlton - Grand Cayman was nothing short of spectacular. The hotel's elegant design, combined with its top-notch amenities, made for a truly relaxing and enjoyable experience. The staff went above and beyond to ensure my comfort and satisfaction. We can wait to be back again next year!
Reviewed on 1 Oct 2025
Don't see what you're looking for?
See all available trips from Hartford to Grand Cayman
View all trips
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way, Seven Mile Beach, Grand Cayman
Stay at this 5-star 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! (905 reviews)
Couples like: full-service spa, couples spa treatments, poolside dining, hot tub
Travellers say...
"Amazing place like a heaven very very kind and friendly staff they upgraded our room without any charge beach is amazing"
Reviewed on 27 Sept 2025
Wyndham Reef Resort Grand Cayman
2221 Queens Highway, Collier's Bay, East End, Grand Cayman
Stay at this 3.5-star beach resort in East End. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
8.2/10 Very Good! (1,010 reviews)
Couples like: full-service spa, couples spa treatments, restaurant with ocean view, on the beach
Travellers say...
"It is very nice,food is very expensive and that is common on the Island. They are working on the Sargassum which Mother Nature controls that issue. It is a drive to most visited areas. The kitchen is nice to have,the studio could use a table to eat at. Ceiling fan needs to be set on a higher speed ..."
Reviewed on 27 Aug 2025
The Ritz-Carlton, Grand Cayman
West Bay Road, PO Box 32348 KY1-1209, Seven Mile Beach, Grand Cayman
Stay at this 5-star luxury resort in Seven Mile Beach. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff in our ...
9.4/10 Exceptional! (1,002 reviews)
Couples like: full-service spa, beachfront dining, Hot tub, on the beach
Travellers say...
"Very nice place, with amazing Sunsets :) I'll definitely come back here :)"
Reviewed on 25 Sept 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
