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Spend 4 Nights in Sint Maarten from $530 — Award-Winning 5⭐️ Beach Resort & Flights Included
From $530
Step 2: Book FlightsCheapest FlightsPirates, we rarely find such cheap rates on a Sint Maarten vacation! From $482 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 $1,200, so you can save over 50% off today! We've found these excellent-value prices on plenty of dates through December.
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 Washington, DC
🔻 Departing Fort Lauderdale
🔻 Departing Toronto
🔻 Departing Montreal
🔻 Departing NYC
🔻 Departing New Orleans
🔻 Departing Dallas
🔻 Departing Boston
🔻 Departing Atlanta
🔻 Departing Philadelphia
🔻 Departing Chicago
🔻 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 $225 per person!
Hotel Price per Person = $225
Flight Price = $305
TOTAL = $530 [Based on Two Guests]