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Vacation Rentals & Villas in Simpson Bay

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Vacation Rentals & Villas in Simpson Bay

About Simpson Bay

2,243 villas

Beachfront gated Condo directly on Simpson Bay

Simpson Bay apartment

2 bedrooms / 3 bathrooms / sleeps 5

Responds fast! avg. 2 hours 9 minutes

1 / 16

2BR-Oceanfront-Royal Palm

Simpson Bay condo

2 bedrooms / 2 bathrooms / sleeps 6

1 / 10

Sapphire Ruby Suite - Unforgettable Getaway!

Simpson Bay condo

1 bedroom / 1 bathroom / sleeps 4

1 / 23

The Atrium Beach Resort and Spa - Two Bedroom

Simpson Bay house

2 bedrooms / 2 bathrooms / sleeps 4

1 / 18

Coral Breeze - STM

Simpson Bay villa

5 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 37 minutes

1 / 16

Villa Casa Carib, Luxuary 2 Bedroom/2 Bath on Simpson Bay Beach

Simpson Bay villa

2 bedrooms / 2 bathrooms / sleeps 4

1 / 20

Le Papillon - REOPENED AFTER IRMA - Modern Beachfront Unit with great view

Simpson Bay apartment

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 13 minutes

1 / 28

BEACHFRONTBLISS

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

1 / 15

Tropical Paradise Villa at Coral Shores in Pelican

Simpson Bay villa

2 bedrooms / 2 bathrooms / sleeps 4

1 / 22

1 Bed Luxury Condo

Simpson Bay condo

1 bedroom / 1 bathroom / sleeps 2

1 / 14

Coco Beach #5 ON THE BEACH

Simpson Bay apartment

2 bedrooms / 5 bathrooms / sleeps 6

1 / 9

The Sapphire: Pearl Suite - Peace of mind!

Simpson Bay condo

1 bedroom / 1 bathroom / sleeps 4

1 / 22

2 BEDR townhouse overlooking OCEAN ST- MAARTEN

Simpson Bay house

2 bedrooms / 1 bathroom / sleeps 4

1 / 20

Le Papillon Penthouse - The most amazing beachfront property

Simpson Bay apartment

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 13 minutes

1 / 23

Simpson Bay Beach Modern Luxury Ocean View Private Roof Deck 360° views WIFI

Simpson Bay apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 38 minutes

1 / 32

SAPPHIRE... A casual, comfortable villa with ocean views in Pelican Key!

Simpson Bay villa

3 bedrooms / 3 bathrooms / sleeps 6

1 / 13

BEACHSIDE CONDO... You can't get much closer to the beach than this!!

Simpson Bay apartment

3 bedrooms / 3 bathrooms / sleeps 6

1 / 18

Blue Pelican Luxury Villas - Featured on HGTV!!!!!

Simpson Bay apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 4 minutes

1 / 14

TARA... Affordable oceanfront villa, walk to beach

Simpson Bay villa

5 bedrooms / 5 bathrooms / sleeps 10

1 / 47

Amazing View Penthouse apartment on Simpson Bay Beach WE ARE BACK AFTER IRMA

Simpson Bay apartment

2 bedrooms / 3 bathrooms / sleeps 4

1 / 13

SIMPSON BAY BEACH CONDO #3...right on the beach at Simpson Bay

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

1 / 14

Condo Danielle

Simpson Bay condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 23 minutes

1 / 13

COCO BEACH CLUB #5.... step out the door on to the soft white powdery sand of S

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

1 / 29

Studio in Pelican Key Paradise

Simpson Bay apartment

/ 1 bathroom / sleeps 2

1 / 11

Carisma on the beach

Simpson Bay villa

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 46 minutes

1 / 22

The Sapphire: Aquamarine Suite- Breathtaking views!

Simpson Bay condo

1 bedroom / 1 bathroom / sleeps 4

1 / 22

VILLA BEAUTIFUL LOVE SXM

Simpson Bay villa

5 bedrooms / 4 bathrooms / sleeps 12

1 / 28

Beachfront Condo

Simpson Bay condo

2 bedrooms / 3 bathrooms / sleeps 4

1 / 9

Unrivaled Luxury Villa with beach access

Simpson Bay house

5 bedrooms / 5 bathrooms / sleeps 10

1 / 18

Modern Luxury Directly on the Beach

Simpson Bay condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 59 minutes

1 / 17

COLONY MANOR GUEST COTTAGE... Romantic hideaway right on Simpson Bay Beach!

Simpson Bay studio

Studio / 1 bathroom / sleeps 2

1 / 13

WITENBLAUW... Magical Beach Front Estate on Pelican Key

Simpson Bay villa

6 bedrooms / 6 bathrooms / sleeps 12

1 / 61

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

Simpson Bay villa

5 bedrooms / 5 bathrooms / sleeps 10

1 / 38

IL PUNTO BLUE...Located right on the beach in prestigious Pelican Key

Simpson Bay apartment

3 bedrooms / 4 bathrooms / sleeps 6

1 / 40

Coco Beach Duplex

Simpson Bay villa

2 bedrooms / 3 bathrooms / sleeps 4

Responds fast! avg. 37 minutes

1 / 21

Beautiful Studio in Pelican Key /Simpson Bay

Simpson Bay apartment

1 bedroom / 1 bathroom / sleeps 2

1 / 9

SUNSHINE VILLA... Huge, affordable beachfront villa, full AC, walk to restaurant

Simpson Bay house

5 bedrooms / 6 bathrooms / sleeps 10

1 / 39

Beach Front Property - Spectacular Sunset

Simpson Bay villa

5 bedrooms / 5 bathrooms / sleeps 16

1 / 22
Viewing 38 of 2,243

About Simpson Bay

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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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