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Vacation Rentals & Villas in Simpson Bay

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Vacation Rentals & Villas in Simpson Bay

About Simpson Bay

2,321 villas

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 55 minutes

Price per night from

$299

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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

Price per night from

$144

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Coco Beach #5 ON THE BEACH

Simpson Bay apartment

2 bedrooms / 5 bathrooms / sleeps 6

Price per night from

$372

1 / 9

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

Simpson Bay apartment

1 bedroom / 1 bathroom / sleeps 2

“Excellent place to stay.” The pre-trip information was perfect and the welcome "meet and greet" was perfect and thorough too. We stayed in Villa #2. Essentially, you couldn't wish for more on the inside - serious attention has been paid to detail and

Responds fast! avg. 2 hours 46 minutes

Price per night from

$169

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Beachfront gated Condo directly on Simpson Bay

Simpson Bay apartment

2 bedrooms / 3 bathrooms / sleeps 5

“Right on the beach. Best location on Simpson Beach” On our 7th trip to St. Maarten, my husband and I decided to break free from the typical hotel experience, we booked a week at this condo on Simpson Bay Beach... and I'm so glad we did! The condo itse

Responds fast! avg. 2 hours 4 minutes

Price per night from

$250

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BEACHFRONTBLISS

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$300

1 / 15

Carisma on the beach

Simpson Bay villa

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 27 minutes

Price per night from

$230

1 / 22

2BR-Oceanfront-Royal Palm

Simpson Bay condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$350

1 / 10

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

Simpson Bay villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$243

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Le Papillon Penthouse - The most amazing beachfront property

Simpson Bay apartment

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 55 minutes

Price per night from

$399

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Cool Bay Villa St Maarten

Simpson Bay house

2 bedrooms / 1 bathroom / sleeps 4

“Quiet and relaxing” We spent 20 days of vacation with my whole family,Valerie and Philippe offered a good service, the house is friendly and perfect for a family,the place is safe and there is a private car park. We had a good time and would recommend

Price per night from

$89

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2 BEDR townhouse overlooking OCEAN ST- MAARTEN

Simpson Bay house

2 bedrooms / 1 bathroom / sleeps 4

“Fabulous resort living with a tropical breeze!” A most wonderful place to enjoy all St Maarten has to offer! Beautiful, airy, spotless accommodations with a contemporary Carribean decor and all the amenities you need for a wondrous vacation! Centrally

Price per night from

$214

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Villa Sapphire - Ideal for Couples and Families, Beautiful Pool and Beach

Simpson Bay villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$358

1 / 14

Belle Amour - Ideal for Couples and Families, Beautiful Pool and Beach

Simpson Bay villa

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$543

1 / 16

Contemporary penthouse at La Brisas

Simpson Bay apartment

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$454

1 / 26

Unrivaled Luxury Villa with beach access

Simpson Bay house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$645

1 / 18

Caribbean Blue - Ideal for Couples and Families, Beautiful Pool and Beach

Simpson Bay villa

5 bedrooms / 6 bathrooms / sleeps 2

Price per night from

$642

1 / 22

1 Bed Luxury Condo

Simpson Bay condo

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$150

1 / 14

Steps to Caribbean, pool and 2 mile-long beach

Simpson Bay apartment

1 bedroom / 2 bathrooms / sleeps 2

Price per night from

$225

1 / 33

PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW

Simpson Bay apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 59 minutes

Price per night from

$120

1 / 12

BISOU DU SOLEIL ... IRMA Survivor !! (Formerly Riviera) 3 BR hillside villa Pel

Simpson Bay villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$671

1 / 50

Pelican Key 1Bedroom For Rent

Simpson Bay hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$230

1 / 9

Riviera - Ideal for Couples and Families, Beautiful Pool and Beach

Simpson Bay villa

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$415

1 / 22

SEA BEACH TREASURE...Irma Survivor!! Gorgeous 2BR Penthouse on Simpson Bay Beach

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$570

1 / 40

Faja Lobie - Ideal for Couples and Families, Beautiful Pool and Beach

Simpson Bay villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$412

1 / 25

VILLA BEAUTIFUL LOVE SXM

Simpson Bay villa

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$720

1 / 28

Beachfront Retreat. Newly renovated modern apartment on the beach side

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$260

1 / 10

Condo Danielle

Simpson Bay condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 26 minutes

Price per night from

$129

1 / 13

Sapphire Ruby Suite - Unforgettable Getaway!

Simpson Bay condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$185

1 / 23

Beautiful Studio in Pelican Key /Simpson Bay

Simpson Bay apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$90

1 / 9

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

Price per night from

$500

1 / 29

La Vista Grande - Ideal for Couples and Families, Beautiful Pool and Beach

Simpson Bay villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$529

1 / 24

SIMPSON BAY BEACH CONDO #2...located right on the beach at beautiful Simpson Bay

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$514

1 / 22

The Sapphire: Pearl Suite - Peace of mind!

Simpson Bay condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$172

1 / 22

Modern Luxury Directly on the Beach

Simpson Bay condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 59 minutes

Price per night from

$275

1 / 17

Caribbean Sun

Simpson Bay condo

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$300

1 / 34

Price per night from

$179

1 / 22

1Bedroom in Pelican Key

Simpson Bay apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$275

1 / 11
Viewing 38 of 2,321

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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