WINTER🌴 Vacation on Cayman Islands from $845 p.p: flights from US cities + 5-night accommodation

Why book this deal?

🌴 Escape the Cold: Trade winter’s chill for a tropical paradise with guaranteed sunshine and low humidity.
🌴 Perfect Diving Conditions: Winter offers the best underwater visibility for exploring the islands’ famous coral reefs and marine life.
🌴 Calm Seas: The Caribbean Sea is at its most tranquil, providing ideal conditions for all water sports and activities.
🌴 Festive Season: Experience a unique blend of local culture and holiday cheer with the islands’ festive events.

For your tropical vacation on Cayman Islands, book a stay at the well-rated 3*Cobalt Coast Resort situated on the quiet West Bay coastline of Grand Cayman. The resort is built to cater to the diving community, with a prime oceanfront location that provides direct access to spectacular shore diving and snorkeling right from its own dock. Guests can enjoy comfortable, ocean-facing rooms and suites, a freshwater pool, and an on-site restaurant and bar.

Travel dates:
January 22-27, 2026

Route:
Miami – Grand Cayman – Miami
New York – Grand Cayman – New York
Denver – Grand Cayman – Denver
Austin – Grand Cayman – Austin
Chicago – Grand Cayman – Chicago

Price breakdown (based on 4 people sharing):
flights from US cities – from $1224
5 nights at hotel – $2154
Total: from $3378/$844.5 per person

Baggage allowance:
Check out airline policy for baggage allowance

Please note: All the information on this page is correct at the time of publication. If you are checking out the deal at a later date, the price and the availability may no longer be as advertised. Prices are subject to change. To ensure you never miss our deal again, sign up for email notifications >>

Photo credit: booking.com