Vacation Rentals & Villas in Simpson Bay

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780 villas

2BR-Oceanfront-Royal Palm

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$443

Sapphire Ruby Suite - Unforgettable Getaway!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$210

BEACHFRONTBLISS

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$337

TARA... Affordable oceanfront villa, walk to beach

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$644

The Sapphire: Pearl Suite - Peace of mind!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$196

1 Bed Luxury Condo

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$168

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

$140

TOP OF THE ART PENTHOUSE

Simpson Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 4 minutes

Price per night from

$608

The Sapphire: Aquamarine Suite- Breathtaking views!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$210

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

$267

Steps to Caribbean, pool and 2 mile-long beach

Simpson Bay apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Price per night from

$253

Studio in Pelican Key Paradise

Simpson Bay apartment

  • 1 bathroom
  • sleeps 2

Price per night from

$168

15 steps away from the beach

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$145

Pearl on the Beach

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$577

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

$225

Price per night from

$554

Beachfront Condo

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$577

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

Simpson Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$490

WITENBLAUW... Magical Beach Front Estate on Pelican Key

Simpson Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 17

Price per night from

$2,028

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

Responds fast! avg. 20 minutes

Price per night from

$309

Price per night from

$630

1Bedroom in Pelican Key

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Price per night from

$309

CASA DE BELLA... Great location at a great price!!

Simpson Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$253

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

$329

The Sapphire: Turquoise Suite - Tranquility!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$210

Pelican Key 1Bedroom For Rent

Simpson Bay hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$258

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

$390

Ocean Front with Private Pool

Simpson Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$281

Beach Heaven

Simpson Bay penthouse

  • 2 bedrooms
  • 6 bathrooms
  • sleeps 4

Price per night from

$337

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

$337

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

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$386

Popular Beachfront property/ Barefoot in SXM

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$297

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

$196

ATLANTIS... Beachfront on Simpson Bay - totally redone after Irma!

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$267

LUXURIOUS 2 BEDROOM CONDO ON SIMPSON BAY

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$617

Sapphire Suite - Indulgent retreat!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$217

Viewing 38 of 780
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!

Top Destination reviews

ATLANTIS... Beachfront on Simpson Bay - totally redone after Irma!
Cant get closer to the beach!

location was fantastic. apartment was plenty roomy. kitchen was well appointed. easy walk for groceries & to bakery for baguettes and croissants. nice music from mary's Boon just 2 doors down. couple of lovely spots to eat or drink an easy walk down the beach. We also walked to many restaurants along Welfare road simpson bay, easy 5-10 min walk. Driving over to Maho took only about 10 minutes. Room for improvement: need a better mattress. would be really nice to have lounge chair to take to beach and maybe one more chair in the living room, currently there is only a futon.see more
Pelican Key 1Bedroom For Rent
Great location, great resort, great service!

Just wanted to give a quick thank you and let folks know what a great time we had on our July, 2012 vacation in St Maarten at the atrium Beach Resort. Jackie (the lady who booked our condo) told us the place was being renovated and couldn't say if we would be in a new or "old" unit, oceanfront or non oceanfront, but for the price, we were totally fine with any 1BR. We ended up in a renovated room, oceanfront and of course thought we would owe more because the unit was worth way more than what we paid. Everyone at the resort was great. The pool was great. The location was great. Be sure to go to the Greenhouse downstairs for some great prime rib on Mondays and Crab Legs on Wed (I think I have the nights right, but check to be sure). And the Buccaneer Beach Bar is great on Fri nights for a fire on the beach which is actually in a ball with sculptured cut outs all around. I will definitely return to the atrium and will definitely use Jackie again for all my future bookings.see more
2 BEDR townhouse overlooking OCEAN ST- MAARTEN
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 located; walk to local French bakery , intimate Piano Bar, beautiful white sand beaches, beachside coctail bars, restaurants, shopping, etc! Parking for a rental car so you can hop all around the island. We enjoyed an absolutely fabulous time here..and at the end of the day a relaxing time gazing out at the turquoise ocean from our veranda!see more
Cool Bay Villa St Maarten
Very good first Time in st marteen

Nothing else to say but excellent!! Valérie and Philippe are so kind with their tourists. Everything was so easy with them. Lovely Island and so many beaches "We will go again and again" according to my kids!! … see more

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