Vacation Rentals & Villas in Simpson Bay

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Sapphire Ruby Suite - Unforgettable Getaway!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$212

BEACHFRONTBLISS

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$344

TARA... Affordable oceanfront villa, walk to beach

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$658

The Sapphire: Pearl Suite - Peace of mind!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$197

1 Bed Luxury Condo

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$172

The Sapphire: Aquamarine Suite- Breathtaking views!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

$229

CARIBBEAN BLUE... 5BR beachfront home in Pelican Key

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$915

Steps to Caribbean, pool and 2 mile-long beach

Simpson Bay apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Price per night from

$258

Studio in Pelican Key Paradise

Simpson Bay apartment

  • 1 bathroom
  • sleeps 2

Price per night from

$172

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

Price per night from

$558

BISOU DU SOLEIL... beautiful, immaculate, affordable villa in Pelican Key

Simpson Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$500

WITENBLAUW... Magical Beach Front Estate on Pelican Key

Simpson Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 17

Price per night from

$3,000

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

Modern Luxury Directly on the Beach

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$315

Price per night from

$671

1Bedroom in Pelican Key

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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

$215

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

$429

The Sapphire: Turquoise Suite - Tranquility!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

$442

Ocean Front with Private Pool

Simpson Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$287

Beach Heaven

Simpson Bay penthouse

  • 2 bedrooms
  • 6 bathrooms
  • sleeps 4

Price per night from

$344

EL Zafiro: Emerald Suite - A Gem within a Gem!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$390

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

$215

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

$508

LUXURIOUS 2 BEDROOM CONDO ON SIMPSON BAY

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$630

Sapphire Suite - Indulgent retreat!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$219

Price per night from

$229

Sapphire: Peridot Suite - Iconic Views

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$197

Beach view

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$585

SEAS THE PARADISE... Fabulous Beachfront Condo at Las Arenas on Simpson Bay!

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$386

Ocean View Studio w/ WiFi, Beach Access, Resort Pool & More!

Simpson Bay studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 49 minutes

Price per night from

$243

Price per night from

$357

the beacon

Simpson Bay house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$147

Viewing 38 of 1,054
rentals in Simpson Bay

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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!

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