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Spend 4 Nights in Sint Maarten from $436 Each — Award-Winning 5-Star Beach Resort & Flights Included!
From $436
Book FlightsCheapest FlightsPirates, we rarely find such cheap rates on a Sint Maarten vacation! From $436 each, 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) in a suite for four guests. Enjoy a private beach, five pools, a spa, live entertainment, and more.
Sint Maarten getaways are notoriously expensive, with similar group vacations costing over $1,000 each, so you can save over 50% off today! We've found these excellent-value prices on summer and fall dates through November.
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 Washington, DC
🔻 Departing New Orleans
🔻 Departing Chicago
🔻 Departing Houston
🔻 Departing Dallas
🔻 Departing NYC
🔻 Departing Toronto
🔻 Departing Atlanta
🔻 Departing Philadelphia
🔻 Departing Montreal
🔻 Departing Boston
Pirate Tip 🏴☠️️: select the lowest price option on Trivago to get the best deal.
*That's $131 per person when split between four guests!
Hotel Price per Person = $131
Flight Price = $305
TOTAL = $436 [Based on Four Guests]