Holiday Rentals in Simpson Bay
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Unlock member prices with Mates Rates
You could save 10% or more on over 100,000 hotels right now.
Check rental availability in Simpson Bay
Holiday Rentals in Simpson Bay

Hilton Vacation Club Royal Palm St. Maarten

The Hills Residence

Simpson Bay Suites

Tradewinds at Simpson Bay

Oceanfront amazing 2 BR Villa - 2 min from the beach

One Hundred Million Dollar Yacht On Land 5 star Beachhoiuse on the Ocean

4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea

3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at 250/nt!!

Blue Sail Apartments - Two bedroom apartments

Nice and cozy ocean front studio with private terrace. Short walk to beaches.

Dream Beachfront Home : Stunning sea views, private pool and walking distance

Oceanfront amazing 2 bedrooms Condo

Maho Beach House - Spacious 1 Bedroom Suite

Stunning Beach Front Villa With Infinity Pool

Maho Beach Modern 1-Bedroom, Ocean Level

Large 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay
Other types of properties in Simpson Bay you may be interested in

The Morgan Resort Spa Village
Holiday Accommodation Simpson Bay
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Simpson Bay are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Simpson Bay itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Simpson Bay holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Simpson Bay, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Simpson Bay with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
More Destinations
- Maho Hotels
- Maho Reef Hotels
- Apartment Hotels in Sint Maarten
- Hotels with Free Airport Shuttle in Sint Maarten
- Pet Friendly Hotels in Sint Maarten
- Hotels with a Waterpark in Sint Maarten
- Sint Maarten Hotels
- Aparthotels in Sint Maarten
- B&B in Sint Maarten
- Cottages in Sint Maarten
- Hostels in Sint Maarten
- Houseboats in Sint Maarten
- Villas in Sint Maarten
- Cole Bay Hotels
- Hotels near Philipsburg Boardwalk
- Hotels near Indigo Beach
- Tamarind Hill Estates Hotels
- Philipsburg Hotels
- Hotels near Lay Bay Beach
- Oyster Pond Hotels
- Hotels near Princess Juliana Intl.










