Simpson Bay villas
We found 1,209 villas — enter your dates for availability
Explore Simpson Bay villa rentals

One Hundred Million Dollar Yacht On Land 5 star Beachhoiuse on the Ocean
Sleeps 6 · 3 bedrooms · 3 bathrooms

Oceanfront amazing 2 BR Villa - 2 min from the beach
Sleeps 4 · 2 bedrooms · 2 bathrooms

3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT & PRIVATE POOL! From 250/nt!!
Sleeps 6 · 3 bedrooms · 3 bathrooms

4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea
Sleeps 8 · 4 bedrooms · 3 bathrooms

Luxurious Villa " Sea La Vie" in Pelican Key
Sleeps 6 · 3 bedrooms · 3 bathrooms

Stunning Beach Front Villa With Infinity Pool
Sleeps 10 · 4 bedrooms · 5 bathrooms
Find spaces that suit your style
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- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
Are there any holiday villa rentals in Simpson Bay?
You can choose from 1,209 villa rentals in Simpson Bay that have more space for your next group or family escape, and plenty of old-world appeal. Browse Bookabach's villas in sought-after areas such as Pelican Key, Cay Bay and Almond Grove.
How much does it cost to stay in a villa rental in Simpson Bay?
Prices vary according to length of stay, season and exact property location, so key in your trip details to find out what's available. Whatever your plans or budget, Bookabach has villa rentals in Simpson Bay suited to guests of all types.
When is the best time to rent a villa in Simpson Bay?
With average temperatures ranging between 25ºC and 26ºC, March is when the majority of our guests book a villa rental in this corner of Saint Martin. If you'd like to travel to Simpson Bay at this busy time, book in advance to get the best availability.
Where can I rent a Simpson Bay villa with great views?
If you want your break to come with scenic beach views, we've got some villa rentals in Simpson Bay that'll check all your boxes. Browse for a villa with a view by using our "Highly rated for location" filter under "Property reviews" and see what pops up.
Can I book a luxury villa in Simpson Bay?
Book a villa rental and make your trip to Simpson Bay truly unforgettable. These stays usually feature upmarket amenities, like private terraces, a spa or hot tub and ultra-modern kitchens. With loads of room to accommodate large groups, they're a perfect choice for family reunions and corporate retreats. You'll find some incredible options in the neighbourhood of Pelican Key.
What are the top things to do in Simpson Bay?
Get your Simpson Bay escape off to an amazing start by visiting popular sights like Maho Beach, Mullet Bay Beach and Simpson Bay Beach. Stay in a Bookabach villa rental with the family and then uncover this destination's wonders together.
Why should I book my villa holiday with Bookabach?
With 24-hour customer support, your peace of mind is guaranteed when you book through Bookabach. From the minute you lock in your villa rental to even after your holiday is over, we're with you at every turn. It's all part of our Book with Confidence Guarantee. Plus, we also have an easy and secure payment process and flexible cancellation policies
