Sint Maarten's Private Villa Collection
Your group.
Your villa.
No compromises.
A curated portfolio of professionally managed private villas in Sint Maarten. Full concierge, from chef to yacht. For groups who know the difference between a hotel and a home.
3
Private Villas
6-12
Guests Per Stay
5 ⭐️
Managed Standard
Sint Maarten's Private Villa Collection
Why groups choosing villas
rarely go back to hotels.
The Hotel Experience
Shared spaces, no privacy
Crowded pools, lobby noise, strangers at every turn. You paid for a vacation, not a crowd.
10 rooms across 3 floors
Your group is scattered. You planned a trip together to see the hotel hallway?
Restaurant schedules and dress codes
Breakfast at 8. Reservations required. Dressed by 7. Your vacation, on their timeline.
$350–$500 per room, per night
For a group of 10, that's $3,500–$5,000 per night. For less space and less privacy.
The Obsidian Villa
Your pool. Your beach view. Your rules.
A private villa rental means the entire property belongs to your group. No strangers. No shared amenities.
Everyone under one roof
The whole point of a group trip is being together. Communal living spaces, shared meals, one villa.
Breakfast when you wake up. Dinner when you want.
A private chef. Your kitchen fully stocked before arrival. Meals at your pace, not a restaurant's.
Superior experience at comparable cost
Split across a group of 10, a luxury private villa rental in Sint Maarten frequently costs less per person than comparable hotel rooms.
A group of 10 staying 7 nights in hotel rooms pays $24,500–$35,000 – and still shares a pool with strangers. The same group in an Obsidian villa pays a fraction per person, with the entire property to themselves.
÷ 10
Per person. Private villa.
The Portfolio
Why groups choosing villas
rarely go back to hotels.
View All Properties
- Up to 10 guests
Indigo Bay, Sint Maarten
A curated portfolio of professionally managed private villas in Sint Maarten. Full concierge, from chef to yacht. For groups who know the difference between a hotel and a home.
- 5 Bedrooms
- Private Pool
- Ocean Views
- Up to 8 guests
Sint Maarten
Composed for those who have stayed well before. A considered space — light, quiet, and organized around how groups actually live together.
- 4 Bedrooms
- Private Pool
- Garden
- Up to 12 guests
Upper Prince's Quarter, Sint Maarten
Elevated above the island with panoramic views. Private. Arrived at — not stumbled upon. Suited for the group that wants it all, with no one nearby.
- 6 Bedrooms
- Infinity Pool
- Panoramic Views
The Concierge
Every service a five-star hotel offers. Only yours.
This is what separates a private villa rental from a hotel: when you call, we answer for your group only. Not for the lobby. Not for the couple in room 312.
Our concierge team is based in Sint Maarten. We know the island, the vendors, and the experiences that are worth your time.
Private Chef
Caribbean cuisine, dietary preferences respected, served at your table — not a restaurant's.
Yacht Charters
Full-day and half-day charters throughout Sint Maarten and St. Barths. Pre-arranged and confirmed before you arrive.
Spa Services
In-villa massage, beauty treatments, and wellness — without leaving the property.
Grocery Pre-Stocking
Your kitchen ready before you land. Preferences submitted in advance. Open the refrigerator, not a delivery app.
Bespoke Experiences
Island tours, sunset dinners, birthday arrangements, local guides, private events. If it can be done well on Sint Maarten, we know how to do it.
The Portfolio
Three villas. Each selected for a reason.
View All Properties
Our home island. Dutch side, French side, and every cove in between. We know this island the way a local does.
Beyond the Resort
We live here. You vacation here. That difference matters.
A luxury villa Sint Maarten stay is only as good as the team behind it. Every concierge recommendation, charter captain, and chef we work with has been vetted by us — not by a review algorithm.
The island has two sides, dozens of beaches, and one of the best duty-free shopping districts in the Caribbean. We know which experiences are worth your time and which are tourist traps wrapped in good photography.
01
Local vendor relationships, not hotel commissions
We recommend what we trust, not what pays us a referral fee. The best charter on the island may not be the most marketed one.
02
One contact from inquiry to checkout
Your group has a single point of contact. No ticketing systems. No automated responses. A person, who knows your stay.
03
Professional management — not Airbnb
Each property is professionally managed and inspected. What you see in the photos is what you find when you arrive. There is no version where that is not true.
04
First-time Caribbean travelers, guided well
If Sint Maarten is new to your group, we provide destination knowledge that no resort brochure contains.
The Portfolio
Villas were designed for exactly this
Families
Multi-generational trips with children. Space for everyone, no one in each other's way, everyone together.
Friends
Groups of 6–12 who want a real trip, not a hotel hallway. Shared dinners. Late nights on the terrace.
Celebrations
Birthdays, anniversaries, bachelor and bachelorette trips. Occasions that need a setting — not just a room.
First Caribbean Visit
New to the island? We handle the planning, the questions, and the island knowledge. You handle being there.
"The best Caribbean group travel is a private villa with someone who actually knows the island."
What Guests Say
The experience, in their words.
We've done hotel trips with this group for years. This was the first villa, and we spent most of the week asking why we didn't do it sooner. Having the pool to ourselves, cooking together, the space — it changes everything.
We planned a bachelorette weekend and were nervous about something going wrong. The Obsidian team had everything set before we landed — groceries, flowers, the chef confirmed. Nothing required any of us to stress.
Our first time in Sint Maarten and we had no idea what to do beyond the villa. The team gave us recommendations that felt genuinely local — not the tourist list. The charter they arranged was the best day of the trip.
Our first time in Sint Maarten and we had no idea what to do beyond the villa. The team gave us recommendations that felt genuinely local — not the tourist list. The charter they arranged was the best day of the trip.
Beyond the Resort
Your group deserves a private villa. Sint Maarten is waiting.
Tell us your dates, your group size, and what matters to your trip. We’ll match you to the right villa and handle the rest — from concierge to checkout.
- Professionally Managed
- Full Concierge Included
- Local Sint Maarten Experts
- No Hidden Fees