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4-Night Cayman Islands Vacation with a Beachfront Holiday Inn Resort & Flights from $567 Per Person
From $567
Step 2: Book FlightsCheapest FlightsEscape to the Caribbean with an affordable island getaway to Grand Cayman! This vacation includes flights and four nights at the Holiday Inn Resort Grand Cayman By IHG (rated 4.1/5 on TripAdvisor and a Winner of the 2026 Travelers' Choice Award), all from $567 per person.
Whether you're catching epic sunsets from your private balcony, sipping cocktails pool-side at the Driftwood Bar, or using the free shuttle to beach-hop around Seven Mile Beach, this deal is your ultimate beach escape. We've found the best rates on fall and winter dates through December.
We've highlighted some of the best dates we found below. Want to travel another time? Just adjust the dates when searching to see updated prices.
Please Note: Be sure to avoid flights with long overnight layovers, which may be cheaper.
🔻 Departing From Toronto
🔻 Departing From Miami
🔻 Departing From Montreal
🔻 Departing From Tampa
🔻 Departing From Pittsburgh
🔻 Departing From Washington, DC
🔻 Departing From NYC
🔻 Departing From Nashville
🔻 Departing From Boston
🔻 Departing From New Orleans
🔻 Departing From Austin
🔻 Departing From Raleigh
🔻 Departing From Indianapolis
🔻 Departing From Los Angeles
That's $312 per person for a 4-night stay!
Quiet North Sound views offering a peaceful escape away from the heavy cruise ship crowds
Complimentary beach shuttle making it effortless to reach nearby Seven Mile Beach and Camana Bay
On-site watersports provider for quick access to Stingray City boat tours, jet skis, snorkeling, and kayaks
Adjacent to North Sound Golf Club, the island's only 18-hole championship golf course
Spacious suite options featuring fully equipped kitchens and private balconies for a comfortable, flexible stay
Fresh Caribbean dining at the Driftwood Bar & Grill right beside the resort's ocean-side freshwater pool
For Double Occupancy:
Hotel Price per Person = $312
Flight Price = $255 Round-Trip
TOTAL = $567 Per Person [Flights + 4-Night Stay Included]