Updating...
Price per night from
$212
TARA... Affordable oceanfront villa, walk to beach
Simpson Bay villa
- 5 bedrooms
- 5 bathrooms
- sleeps 10
Price per night from
$659
Price per night from
$197
Simpson Bay Beach Modern Luxury Ocean View Private Roof Deck 360° views WIFI
Simpson Bay apartment
- 1 bedroom
- 1 bathroom
- sleeps 4
Price per night from
$143
Price per night from
$212
COCO BEACH CLUB #5.... Located on the soft white powdery sand of Simpson Bay be
Simpson Bay apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Price per night from
$272
CARIBBEAN BLUE... 5BR beachfront home in Pelican Key
Simpson Bay villa
- 5 bedrooms
- 5 bathrooms
- sleeps 10
Price per night from
$916
Price per night from
$258
Price per night from
$148
MARISOL... Light and airy townhouse at Point Blue in Pelican Key Estate
Simpson Bay apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Price per night from
$229
SOL Y MAR... fabulous beachfront penthouse on Kimsha Beach! Private pool, Walk t
Simpson Bay villa
- 3 bedrooms
- 3 bathrooms
- sleeps 8
Price per night from
$559
BISOU DU SOLEIL... beautiful, immaculate, affordable villa in Pelican Key
Simpson Bay villa
- 3 bedrooms
- 3 bathrooms
- sleeps 6
Price per night from
$499
WITENBLAUW... Magical Beach Front Estate on Pelican Key
Simpson Bay villa
- 6 bedrooms
- 7 bathrooms
- sleeps 17
Price per night from
$2,073
COCO BEACH CLUB 6...walk out onto the sand of Simpson Bay Beach
Simpson Bay condo
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Price per night from
$229
Responds fast! avg. 20 minutes
Price per night from
$315
PROVENCE... Affordable villa, gorgeous views, close to dining, shopping, casinos
Simpson Bay villa
- 6 bedrooms
- 5 bathrooms
- sleeps 12
Price per night from
$642
Price per night from
$315
CASA DE BELLA... Great location at a great price!!
Simpson Bay house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
Price per night from
$258
IL PUNTO BLUE...Located right on the beach in prestigious Pelican Key
Simpson Bay apartment
- 3 bedrooms
- 4 bathrooms
- sleeps 6
Price per night from
$428
Price per night from
$212
RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit on a great beach!
Simpson Bay apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Price per night from
$441
Price per night from
$287
The Blue Frenchie: Gorgeous 2-story townhouse in Pelican Key, St. Maarten
Simpson Bay house
- 2 bedrooms
- 3 bathrooms
- sleeps 5
Price per night from
$344
Price per night from
$390
Price per night from
$304
Catamaran - Fully-Crewed & All-Inclusive - St. Martin, Caribbean
Simpson Bay yacht
- 3 bedrooms
- 3 bathrooms
- sleeps 6
Price per night from
$2,000
COLONY MANOR GUEST COTTAGE II... Romantic hideaway right on Simpson Bay Beach!
Simpson Bay apartment
- 1 bedroom
- 1 bathroom
- sleeps 2
Price per night from
$200
ATLANTIS... Beachfront on Simpson Bay - totally redone after Irma!
Simpson Bay apartment
- 1 bedroom
- 1 bathroom
- sleeps 2
Price per night from
$272
UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!
Simpson Bay apartment
- 2 bedrooms
- 3 bathrooms
- sleeps 4
Price per night from
$509
Price per night from
$630
Price per night from
$219
SUNSHINE VILLA... Huge, affordable beachfront villa, full AC, walk to restaurant
Simpson Bay house
- 5 bedrooms
- 6 bathrooms
- sleeps 10
Price per night from
$773
Viewing 38 of 1,251
rentals in Simpson Bay
About Simpson Bay
The beach at Simpson Bay is wide, and over a mile long—a stretch of glorious, uninterrupted sand. The blue waters of the Caribbean lap the shore, providing the perfect backdrop for a relaxing vacation.
But it’s not all relaxation—the main streets of Simpson Bay are bustling hives of activity with bars, restaurants and stores. Why not start searching FlipKey for the perfect vacation rental and plan your perfect trip?
About Simpson Bay, St. Maarten-St. Martin
Many years ago, Simpson Bay was home to the fishermen of the island and their families. Now, it's a popular tourist destination, although the fishermen still ply their trade. The first inhabitants of Simpson Bay and the surrounding area were the Arawaks, from the Amazon basin.
Named after St Martin of Tours, it first appeared on a map in 1516 as Sam Mtim. It was already a Spanish territory by then, though it wasn't a colony. The island has been in the hands of the Spanish, Dutch and French. Today, the island is shared by the Dutch and French whose cultures still influence life on the island.
The cuisine on the island is international, but you can find some traditional food if you look hard enough. Ask a local for their recommendations to discover some authentic places to eat.
Simpson Bay has a vibrant nightlife which contrasts with the peace you can find on Simpson Bay beach. You'll get the best of both worlds here!
What to do in Simpson Bay, St. Maarten-St. Martin
As Saint Maarten-St Martin is an island, water sports are very popular. Why not try some?
If you're looking for a more calming vacation, swim in the clear blue waters, or relax on the beach.
Try a Rhino Safari excursion on a Rhino Rider—an inflatable motorboat. Pilot your own craft and go snorkeling with a guide.
Charter a yacht for a sunset cruise, or hire a 4x4 and go in a guided convoy to see the sights on both the French and Dutch side of the island. This tour will take you to Oyster Pond, Maho Beach and you'll have two hours to laze on Orient Beach.
Traveling with the kids? If the beach is too hot for them, head to the Butterfly farm—it's a great day out.
Happy Bay Beach is for nudists. If you're feeling adventurous, go there for an all-over tan.
Top travel tips for St. Marteen-St. Martin
It's best to rent a car on St. Maarten-St Martin as you'll have the freedom to explore the island in our own time. That being said, there are taxis and local buses if you don't want to bother.
If you do drive, watch out for potholes! If you can find an all-terrain vehicle to rent, do. It'll definitely be worth it!
You will probably find, on both the French and Dutch sides of the island, that a service charge is included in your restaurant bills. Of course, if the service was very good, you can leave an extra cash tip.
There's plenty to do and see on St. Maarten-St. Martin, whichever side of the island you visit, the Dutch or French. Go around the island and see it all!
For a wide choice of accommodation, search the rental properties available here on FlipKey and book your next trip. You won’t be disappointed!
Top Destination reviews
Also consider
- Oyster Pond 66 properties
- Cupecoy Bay 55 properties
- Philipsburg 50 properties
- Maho 20 properties
- Cole Bay 11 properties
- Pelican Key 9 properties
- Dawn Beach 6 properties
- Sint Maarten 304 properties
- Dominican Republic 4,822 properties
- Jamaica 1,988 properties
- Martinique 1,200 properties
- Barbados 1,027 properties
- Puerto Rico 891 properties
- St. Barthelemy 836 properties
- St. Martin Sint Maarten 831 properties
- Bahamas 681 properties
- St. Lucia 490 properties
- Aruba 483 properties
- US Virgin Isles 426 properties
- Curacao 365 properties
- Turks and Caicos Islands 305 properties
- Cayman Islands 217 properties
- Antigua and Barbuda 195 properties
- Dominica 177 properties
- Bonaire 128 properties
- St. Vincent and the Grenadines 118 properties
- Anguilla 75 properties
- Haiti 45 properties
- Bermuda 34 properties
- Montserrat 19 properties
- Saba 6 properties