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Spend 4 Nights in Sint Maarten from $495 — Award-Winning 5⭐️ Beach Resort & Flights Included
From $495
Book FlightsCheapest FlightsPirates, we rarely find such cheap rates on a Sint Maarten vacation! From $495, you can fly out and spend four nights at the award-winning 5-star Simpson Bay Resort, Marina & Spa (4/5 on TripAdvisor & winner of the 2025 Travelers' Choice Award). Enjoy a private beach, five pools, a spa, live entertainment, and more.
Sint Maarten getaways are notoriously expensive, with similar vacations costing over $1,000, so you can save over 50% off today! We've found these excellent-value prices on winter and spring dates through May.
We found some dates with the best rates for you, but many others are available.
All prices listed are based on nonstop journeys or short layovers.
🔻 Departing Fort Lauderdale
🔻 Departing Philadelphia
🔻 Departing Atlanta
🔻 Departing Dallas
🔻 Departing Toronto
🔻 Departing NYC
🔻 Departing Houston
🔻 Departing Boston
🔻 Departing Chicago
🔻 Departing Washington, DC
🔻 Departing New Orleans
🔻 Departing Montreal
Pirate Tip 🏴☠️️: select the lowest price option on Trivago to get the best deal.
*That's $267 per person!
Hotel Price per Person = $267
Flight Price = $228
TOTAL = $495 [Based on Two Guests]