Simpson Bay
Simpson Bay
Vacation Rentals in Simpson Bay
The heart of the Dutch side — beach bars, dining, and the island's best nightlife, all within walking distance of your front door.
10 properties available
Simpson Bay is where most visitors discover Sint Maarten first — and where many choose to return. The largest bay on the Dutch side, it stretches from the lagoon bridge to the airport, lined with restaurants, beach bars, and a boardwalk that comes alive after dark.
For vacation rental guests, Simpson Bay offers the widest variety of accommodation on the island: beachfront apartments with direct sand access, penthouses with ocean views, and modern condos within walking distance of dozens of restaurants. It's the most convenient base for first-time visitors and the most energetic for repeat travelers who know exactly where they want to eat tonight.
Why Simpson Bay
What makes it special
Beachfront living
Many of our Simpson Bay rentals sit directly on the sand — step off your terrace and onto the beach. No shuttle, no drive, no compromise.
Dining & boardwalk
Waterfront restaurants, Friday-night boat races, and boardwalk dining from casual to upscale. Simpson Bay has the densest concentration of restaurants on the island.
Nightlife hub
Beach bars transition to cocktail spots by 9 PM. The boardwalk and Maho (10 minutes away) stay lively until late. Live music is common; dress codes are casual.
Central location
Simpson Bay sits at the center of the Dutch side. The airport is 10 minutes, Philipsburg is 15, and the French side is 20. Everything is close.
Our Simpson Bay properties
Rentals in Simpson Bay
Location
What's near Simpson Bay
- Maho Beach & plane-watching (10 min)
- Princess Juliana International Airport (10 min)
- Mullet Bay Beach (15 min)
- Grand Case (20 min)
- Philipsburg & Front Street (15 min)
- Cupecoy Beach & cliffs (15 min)
Common questions
About Simpson Bay
Is Simpson Bay good for families?
Yes. The bay has calm, shallow water perfect for children, and the beach is long and gentle. Several of our apartments are within gated complexes with pools. Restaurants are family-friendly and walkable.
What's the nightlife like?
Simpson Bay is the nightlife center of the Dutch side. Beach bars, live music, waterfront dining, and the nearby Maho casino scene. It's lively but not overwhelming — you can always retreat to your rental.
Can I walk to restaurants from my rental?
In most cases, yes. Simpson Bay has the densest concentration of dining on the island. Many of our rentals are within a 5-10 minute walk of 20+ restaurants.
How far is the airport?
About 10 minutes by car. Simpson Bay is close to Princess Juliana Airport, making arrival and departure effortless.
Find your Simpson Bay rental
Browse our beachfront apartments, penthouses, and condos — or tell us what you're looking for and we'll match you.