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Spend 4 Nights in Sint Maarten from $458 — Award-Winning 5⭐️ Beach Resort & Flights Included
From $458
Step 2: Book FlightsCheapest FlightsPirates, we rarely find such cheap rates on a Sint Maarten vacation! From $458 per person, you can fly out and spend four nights at the award-winning 5-star Simpson Bay Resort, Marina & Spa (4.1/5 on TripAdvisor & winner of the 2026 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 plenty of dates through January.
We found some dates with the best rates for you, but many others are available.
Be sure to avoid flights with long overnight layovers, which may be cheaper.
🔻 Departing Toronto
🔻 Departing Washington, DC
🔻 Departing NYC
🔻 Departing Montreal
🔻 Departing Boston
🔻 Departing New Orleans
🔻 Departing Austin
🔻 Departing Fort Lauderdale
🔻 Departing Atlanta
🔻 Departing Chicago
🔻 Departing Philadelphia
🔻 Departing Dallas
🔻 Departing Houston
Pirate Tip 🏴☠️️: To unlock a Trivago Member Price, all you need to do is sign up for a free Trivago member account. It only takes around 2 minutes!
*That's $198 per person!
Hotel Price per Person = $198
Flight Price = $260
TOTAL = $458 [Based on Two Guests]