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4-Night Cayman Islands Vacation with a Beachfront Holiday Inn Resort & Flights from $514 Per Person
From $514
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 $514 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 January.
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 (unless otherwise specified), which may be cheaper.
🔻 Departing From Toronto
🔻 Departing From Miami
🔻 Departing From Tampa
🔻 Departing From Washington, DC
🔻 Departing From Pittsburgh
🔻 Departing From New Orleans
🔻 Departing From Austin
🔻 Departing From Nashville
🔻 Departing From Boston
🔻 Departing From Indianapolis
🔻 Departing From Raleigh
🔻 Departing From NYC
🔻 Departing From Los Angeles (5 Nights Including an Overnight Flight)
That's $272 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 = $272
Flight Price = $242 Round Trip
TOTAL = $514 Per Person [Flights + 4-Night Stay Included]