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Holiday Lettings
> North America
> Caribbean
> St. Maarten - Saint Martin
> Sint Maarten
> Condos and Apartments in Simpson Bay

Condos in Simpson Bay and Apartments – Holiday Lettings - Holiday Rentals Simpson Bay

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196 Holiday homes

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Simpson Bay holiday villa rental

Simpson Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £342 / night

£2,388 / week

1 / 30

Holiday condo in Simpson Bay

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £518 / night

£3,622 / week

1 / 23

Holiday condo in Simpson Bay

Simpson Bay condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £525 / night

£3,673 / week

1 / 19

Condo rental in Simpson Bay

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £291 / night

£2,033 / week

1 / 22

Simpson Bay ski villa to rent.

Simpson Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from £890 / night

£6,231 / week

1 / 30

Holiday condo accommodation

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £487 / night

£3,408 / week

1 / 30

Simpson Bay ski condo to rent.

Simpson Bay condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £574 / night

£4,018 / week

1 / 20

Holiday apartment in Simpson Bay

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £129 / night

£899 / week

1 / 11

Ski villa to rent in Simpson Bay

Simpson Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £215 / night

£1,501 / week

1 / 29

Holiday condo rental

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £414 / night

£2,898 / week

1 / 30

Apartment rental in Simpson Bay

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £383 / night

£2,680 / week

1 / 13

Condo rental in Simpson Bay

Simpson Bay condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £383 / night

£2,680 / week

1 / 30

Holiday apartment in Simpson Bay

Simpson Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £696 / night

£4,873 / week

1 / 30

Simpson Bay holiday condo rental

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £579 / night

£4,052 / week

1 / 30

Simpson Bay ski condo to rent.

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £458 / night

£3,203 / week

1 / 30

Holiday home in Simpson Bay

Simpson Bay house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £113 / night

£791 / week

1 / 29

Holiday apartment in Simpson Bay

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £141 / night

£987 / week

1 / 18

Holiday condo in Simpson Bay

Simpson Bay condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £297 / night

£2,079 / week

1 / 15

Ski condo to rent in Simpson Bay

Simpson Bay condo

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

from £405 / night

£2,835 / week

1 / 20

Ski villa to rent in Simpson Bay

Simpson Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £1,267 / night

£8,865 / week

1 / 30

Simpson Bay ski apartment to rent.

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £463 / night

£3,237 / week

1 / 30

Apartment rental in Simpson Bay

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £144 / night

£1,008 / week

1 / 30

Holiday apartment in Simpson Bay

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £123 / night

£861 / week

1 / 26

Condo rental in Simpson Bay

Simpson Bay condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £552 / night

£3,863 / week

1 / 30

Simpson Bay ski condo to rent.

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £205 / night

£1,429 / week

1 / 22

Holiday condo in Simpson Bay

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £222 / night

£1,552 / week

1 / 25

Simpson Bay holiday condo rental

Simpson Bay condo

  • 2 bedrooms
  • 5 bathrooms
  • sleeps 5

from £311 / night

£2,175 / week

1 / 30

Simpson Bay holiday condo rental

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £460 / night

£3,214 / week

1 / 28

Holiday condo in Simpson Bay

Simpson Bay condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

from £325 / night

£2,273 / week

1 / 13

Simpson Bay holiday condo rental

Simpson Bay condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from £379 / night

£2,652 / week

1 / 21

Ski condo to rent in Simpson Bay

Simpson Bay condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £446 / night

£3,121 / week

1 / 30

Holiday condo in Simpson Bay

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £467 / night

£3,265 / week

1 / 25

Condo rental in Simpson Bay

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £330 / night

£2,308 / week

1 / 30

Holiday apartment in Simpson Bay

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £168 / night

£1,171 / week

1 / 27

Simpson Bay ski home to rent.

Simpson Bay house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £233 / night

£1,630 / week

1 / 30

Holiday villa in Simpson Bay

Simpson Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £905 / night

£6,336 / week

1 / 30

Holiday condo in Simpson Bay

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £475 / night

£3,323 / week

1 / 25

Simpson Bay holiday apartment rental

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £136 / night

£953 / week

1 / 30

Holiday apartment in Simpson Bay

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £105 / night

£729 / week

1 / 20

Simpson Bay holiday condo rental

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £306 / night

£2,142 / week

1 / 30

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Simpson Bay holidays

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 holiday.

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 Holiday Lettings for the perfect holiday 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 holiday, 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 snorkelling 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.

Travelling 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 definightly 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 Holiday Lettings and book your next trip. You won’t be disappointed!

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