CONTEMPORARY OCEANFRONT VILLA WITH PRIVATE POOLN°001
Sint Maarten, Saint Martin
Sea view
From $4,230 per night
Two nations, one island, and the Caribbean at full flavour
Sint Maarten is the Dutch half of the Caribbean's famous two-nation island, sharing its 87 square kilometres with French Saint-Martin. It packs beaches, marinas, casinos and world-class dining into a compact playground, and a private villa above Cupecoy or Simpson Bay gives you pool, sunset and both countries within a twenty-minute drive.
- Cupecoy's cliff-backed coves and sunset-facing luxury villas
- Jets skimming Maho Beach on approach to Princess Juliana Airport
- Simpson Bay Lagoon, a yachting hub with waterside restaurants and bars
- Two countries in one day: Dutch Philipsburg and French Grand Case's gourmet row
- Day sails to Anguilla, St Barts and Saba from the island's marinas
Known forA Dutch-French island split, Maho Beach plane-spotting, Simpson Bay's lagoon and nightlife, Philipsburg's duty-free streets and gourmet Grand Case
Best time to visitDecember to April for the driest, breeziest high season; May and June for value with fine weather
Nearest airportPrincess Juliana International (SXM), one of the Caribbean's main hubs
Ideal forGroups, foodies, sailors and couples wanting beaches with energy, dining and easy island-hopping
ITALIAN-STYLE BEACHFRONT VILLA IN SIMPSON BAY ROADN°002
Sint Maarten, Saint Martin
Sea view
From $2,135 per night
Luxuriously Spacious Villa with Private PoolN°003
Sint Maarten, Saint Martin
Private poolSea view
From $1,510 per night
Ultra Luxe 4 Bedroom Villa with Majestic Sea ViewsN°004
Sint Maarten, Saint Martin
Private poolSea view
From $1,425 per night
GORGEOUS 3BR VILLA IN CUPECOY BEACHN°005
Sint Maarten, Saint Martin
Private poolSea view
From $1,200 per night
Elegant Oceanfront Villa with Contemporary DesignN°006
Sint Maarten, Saint Martin
Private poolSea view
From $1,150 per night
Events not to miss in Sint Maarten
- Early March
St. Maarten Heineken Regatta
One of the Caribbean's largest sailing regattas, drawing hundreds of boats for days of racing followed by legendary shoreside concerts and parties. The island's marinas and bays are at their most spectacular.
- March
SXM Festival
An acclaimed electronic-music festival staged across beaches, jungle and villa venues on both sides of the island, drawing international DJs and a stylish crowd.
- April
Sint Maarten Carnival
Weeks of pageants, soca and steel pan culminate in grand parades and the Carnival Village in Philipsburg around the end of April, the Dutch side's biggest cultural celebration of the year.
Sint Maarten through the seasons
- Winter high season (December – April)
Trade winds, regattas and full swing
The driest, breeziest months bring perfect beach weather and the island's social peak, from the Heineken Regatta to Carnival, with villas booking far ahead for the holidays.
- Late spring (May – June)
High-season weather, low-season calm
Fine, settled days and warm seas continue as the crowds ease, making these the value months for villa stays, sailing days and restaurant-hopping without the waits.
- Summer and early autumn (July – October)
Green hills and empty beaches
Short tropical showers keep the island lush and the beaches quiet; flexible travellers find the calmest prices of the year, with the sea at its warmest.
- Late autumn (November)
The island freshens for the season
Rains taper, restaurants reopen their high-season menus and the marinas fill ahead of December, a rewarding shoulder month for early-bird villa stays.
The Area and Where to Stay
The island has been shared between the Netherlands and France since 1648, and the border is an open, sign-posted formality: two currencies, two cuisines, one easy drive. The Dutch south, Sint Maarten, is the livelier half, holding the international airport, the cruise capital Philipsburg with its duty-free Front Street, and Simpson Bay's lagoon full of yachts and restaurants. The villa heartland is the south-west corner: Cupecoy's low cliffs and coves, neighbouring Beacon Hill and the Simpson Bay hills, where villas take in sunset views towards Saba and Anguilla. Terres Basses, just over the French line, adds famously private beachfront estates. Choose Cupecoy and Simpson Bay for restaurants, marinas and nightlife within minutes, and cross to the French side whenever the mood turns to long lunches and quieter sand.
Things to Do
Beaches set the agenda: Mullet Bay's surf-friendly curve, Cupecoy's cliff-framed coves, family-easy Kim Sha and, over the border, the long sands of Orient Bay. Watch widebody jets skim Maho Beach on final approach, an island signature found nowhere else. The lagoon and marinas make Sint Maarten one of the Caribbean's great sailing bases, with day charters to Anguilla's beaches, chic St Barts or the diving pinnacles of Saba. Snorkel and dive the island's marine park, kitesurf at Le Galion, or hike Pic Paradis, the island's highest point, for a two-nation panorama. Philipsburg offers duty-free shopping and casinos; Marigot, the French capital, answers with harbourside markets and patisseries. Back at the villa, the concierge arranges boat charters, private chefs, provisioning and in-villa spa days.
Food and Local Flavour
This small island is routinely called the culinary capital of the Caribbean, and the claim holds up. Grand Case, a fishing village on the French side, lines its single street with serious restaurants, from creole lolos grilling ribs and lobster to refined French dining rooms. The Dutch side counters with Simpson Bay's waterside seafood, beach bars and international kitchens, plus Philipsburg's famous johnnycakes and callaloo. Local flavour means conch and dumplings, fresh snapper, guavaberry liqueur, the island's own spirit, and rum in every direction. Villa life fits naturally around it: provisioned kitchens, private chefs mixing French technique with Caribbean produce, and the concierge holding the tables that matter in season.
When to Visit
High season runs December to April, when trade winds keep the heat perfect, rain is scarce and the island's social calendar, regattas, festivals, beach parties, is in full swing; villas book earliest around Christmas and New Year. May and June are excellent value with fine weather and warm seas. The wetter months from July to October bring short tropical showers, lush hillsides and quiet beaches; this is also the Atlantic hurricane season, so flexible travellers are rewarded with space and the calmest prices. November freshens the island for the season ahead. The sea stays swimmably warm every month of the year, and sunsets from a west-facing villa terrace are dependable in all of them.
Getting There
Princess Juliana International (SXM) is one of the Caribbean's principal gateways, with direct flights from North America and Europe, including long-standing links to Amsterdam and Paris. The airport sits beside Maho and Simpson Bay, so many villas are under fifteen minutes from the runway, an unusually painless Caribbean arrival. SXM is also the region's hub for hops to St Barts, Anguilla, Saba and Statia by small plane or ferry, making multi-island trips simple. A hire car is worth having to roam both sides of the border freely. The concierge arranges private transfers, car delivery to the villa and onward island connections.