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

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1,168 Holiday homes

Holiday villa in Simpson Bay Beach

Simpson Bay villa

1 bedroom • 1 bathroom • sleeps 4

from £125 / night

£873 / week

1 / 26

Holiday condo with shared pool in Simpson Bay

Simpson Bay condo

2 bedrooms • 2 bathrooms • sleeps 6

from £329 / night

£2,298 / week

1 / 13

Holiday condo rental

Simpson Bay condo

1 bedroom • 1 bathroom • sleeps 4

from £180 / night

£1,257 / week

1 / 7

Simpson Bay holiday apartment rental

Simpson Bay apartment

1 bedroom • 1 bathroom • sleeps 4

from £108 / night

£752 / week

1 / 11

Simpson Bay holiday villa rental

Simpson Bay villa

6 bedrooms • 5 bathrooms • sleeps 12

from £468 / night

£3,272 - £7,053 / week

1 / 43

Holiday villa rental

Simpson Bay villa

2 bedrooms • 3 bathrooms • sleeps 4

from £183 / night

£1,280 / week

1 / 38

Apartment rental in Simpson Bay with shared pool

Simpson Bay apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £449 / night

£3,121 / week

1 / 18

Simpson Bay holiday villa rental

Simpson Bay villa

3 bedrooms • 3 bathrooms • sleeps 6

from £405 / night

£2,836 - £4,726 / week

1 / 16

Holiday villa rental

Simpson Bay villa

3 bedrooms • 3 bathrooms • sleeps 6

“"Wonderful week in St Maarten"” My wife and I travelled to St Maarten with another couple. It was our first visit to this truly wonderful island. the other couple we travelled with were seasoned vsitors and really knew their way around. We enjoyed a specatular new beach destination every day, each was magnificent, all a little different, and every one felt like a new adventure. The hospitality of the locals most top notch and the food delicious. We toured a delicious selection of restaurants at night, some were a bit fancy, others not so much but in each instance the food was delicious. Loved the island. Our Villa was perfect, great location, close to airport and a good jumping off point for our daily travels. The Villa is large, clean, and comfortable. each bedroom is quite large, great bed, and most importantly each bedroom has its own bathroom. The weather was perfect so we didn't spend much time inside but I liked the living room with it's white painted high vaulted ceiling. Felt very tropical. The highlight is the back private outdoor area with it's own pool, outside room with a dining table, line-up of chaise lounges, and the most spectacular ocean views you can imagine. This villa is the last or end unit in the small gated community of Villa's so there is an un-obstructed view that is breathtaking, particularily at night when the sun is setting. My favourite meal was actulaly in the villa. We went to a local grocery store, picked up a selection of meats and cheeses and a baguette, and enjoyed that with a chilled bottle of sauvignon blanc while watching the sun set and a cruise ship slowly move by. the only downside was I stubbed and broke my toe at one of the beaches. Never-the-less we'll be back to St Maarten and this villa!!

from £333 / night

£2,327 - £3,490 / week

1 / 65

Holiday villa in Simpson Bay

Simpson Bay villa

5 bedrooms • 5 bathrooms • sleeps 10

from £478 / night

£3,345 - £5,744 / week

1 / 47

Holiday home in Simpson Bay

Simpson Bay house

2 bedrooms • 1 bathroom • sleeps 5

from £107 / night

£745 / week

1 / 12

Apartment rental in Simpson Bay with shared pool

Simpson Bay apartment

1 bedroom • 1 bathroom • sleeps 5

from £229 / night

£1,412 / week

1 / 11

Simpson Bay holiday apartment rental

Simpson Bay apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £234 / night

£1,632 / week

1 / 21

Simpson Bay holiday home rental

Simpson Bay house

5 bedrooms • 6 bathrooms • sleeps 10

from £618 / night

£4,326 - £18,177 / week

1 / 33

Holiday apartment accommodation

Simpson Bay apartment

3 bedrooms • 4 bathrooms • sleeps 6

from £343 / night

£2,400 - £4,290 / week

1 / 70

Simpson Bay holiday villa rental

Simpson Bay villa

3 bedrooms • 3 bathrooms • sleeps 6

from £480 / night

£3,359 / week

1 / 32

Holiday villa in Simpson Bay

Simpson Bay villa

6 bedrooms • 6 bathrooms • sleeps 12

from £1,032 / night

£7,219 / week

1 / 35

Holiday condo rental

Simpson Bay condo

1 bedroom • 1 bathroom • sleeps 4

from £154 / night

£1,077 / week

1 / 21

Villa rental in Simpson Bay with swimming pool

Simpson Bay villa

7 bedrooms • 8 bathrooms • sleeps 14

from £1,611 / night

£11,270 - £25,447 / week

1 / 69

Holiday condo with shared pool in Simpson Bay

Simpson Bay condo

2 bedrooms • 3 bathrooms • sleeps 4

from £428 / night

£2,996 / week

1 / 9

Holiday apartment with shared pool in Simpson Bay

Simpson Bay apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £239 / night

£1,673 - £2,545 / week

1 / 41

Holiday apartment with shared pool in Simpson Bay

Simpson Bay apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £255 / night

£1,782 - £3,345 / week

1 / 40

Holiday condo with shared pool in Simpson Bay

Simpson Bay condo

3 bedrooms • 3 bathrooms • sleeps 6

from £250 / night

£1,745 - £3,054 / week

1 / 24

Holiday apartment in Simpson Bay

Simpson Bay apartment

3 bedrooms • 4 bathrooms • sleeps 6

from £245 / night

£1,709 - £2,909 / week

1 / 40

Simpson Bay holiday condo rental

Simpson Bay condo

1 bedroom • 1 bathroom • sleeps 4

from £159 / night

£1,111 / week

1 / 13

Holiday condo rental

Simpson Bay condo

2 bedrooms • 3 bathrooms • sleeps 4

from £428 / night

£2,996 / week

1 / 17

Holiday yacht in Simpson Bay

Simpson Bay yacht

3 bedrooms • 3 bathrooms • sleeps 6

from £1,455 / night

£10,179 / week

1 / 21

Home rental in Simpson Bay with swimming pool

Simpson Bay house

3 bedrooms • 2 bathrooms • sleeps 6

from £291 / night

£2,036 - £2,909 / week

1 / 29

Holiday villa in Simpson Bay

Simpson Bay villa

2 bedrooms • 2 bathrooms • sleeps 4

from £211 / night

£1,475 / week

1 / 17

Holiday condo in Simpson Bay

Simpson Bay condo

1 bedroom • 1 bathroom • sleeps 2

from £143 / night

£1,001 / week

1 / 16

Holiday apartment letting

Simpson Bay apartment

1 bedroom • 2 bathrooms • sleeps 2

from £187 / night

£1,455 / week

1 / 33

Simpson Bay holiday studio rental

Simpson Bay studio

Studio • 1 bathroom • sleeps 4

from £77 / night

£539 - £1,739 / week

1 / 39

Villa rental in Simpson Bay with swimming pool

Simpson Bay villa

5 bedrooms • 4 bathrooms • sleeps 12

from £1,089 / night

£7,620 - £13,087 / week

1 / 34

Simpson Bay holiday condo rental

Simpson Bay condo

2 bedrooms • 3 bathrooms • sleeps 6

from £200 / night

£1,429 - £2,659 / week

1 / 14

Simpson Bay holiday condo rental

Simpson Bay condo

1 bedroom • 1 bathroom • sleeps 4

from £154 / night

£1,077 / week

1 / 16

Studio rental in Simpson Bay

Simpson Bay studio

Studio • 1 bathroom • sleeps 4

from £84 / night

£590 - £1,923 / week

1 / 42

Holiday apartment in Simpson Bay

Simpson Bay apartment

1 bedroom • 1 bathroom • sleeps 2

from £198 / night

£1,382 - £2,182 / week

1 / 36

Simpson Bay holiday apartment rental

Simpson Bay apartment

3 bedrooms • 4 bathrooms • sleeps 8

from £408 / night

£2,851 - £7,189 / week

1 / 41

Simpson Bay holiday condo rental

Simpson Bay condo

1 bedroom • 1 bathroom • sleeps 4

from £143 / night

£1,001 / week

1 / 15

Simpson Bay holiday apartment rental

Simpson Bay apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £468 / night

£3,272 / week

1 / 14

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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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