Simpson Bay Vacation Rentals, House Rentals & More


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Areas near Simpson Bay

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1 / 43

Caribbean Blue at Pelican Key, Saint Maarten - Beachfront, Amazing Sunset View

  • 5
  • 10
  • Min stay varies

$843

Details

1 / 20

Sur Mer is a beachfront condo located in Simpson Bay

  • 3
  • 6
  • 5 nights min

$343

Details

1 / 30

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

  • 3
  • 6
  • Min stay varies

$215

Details

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The Sapphire: Aquamarine Suite- Breathtaking views!

  • 1
  • 4
  • 3 nights min

$149

Details

1 / 24

CARISMA on the BEACH... Totally charming beachfront 2BR in great location!

  • 2
  • 6
  • Min stay varies

$258

Details

1 / 13

★ BRAND NEW CONDO A FEW STEPS FROM SIMPSON BAY BEACH ★

  • 3
  • 6
  • Min stay varies

$370

Details

2
1 / 14

RENDEZVOUS... at Las Arenas.., a fabulous 2 BR contemporary 2 BR condo unit on

  • 2
  • 4
  • Min stay varies

$340

Details

9
1 / 65

WOW WOW WOW, STUNNING INSIDE AND OUT! VILLA LIBRE`

  • 3
  • 7
  • Min stay varies

$400

Details

1
1 / 61

WITENBLAUW... Magical Beach Front Estate on Pelican Key

  • 6
  • 12
  • Min stay varies

$1800

Details

6
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Le Papillon Penthouse - Stunning, modern beachfront unit with private roof top

  • 3
  • 8
  • Min stay varies

$450

Details

2
1 / 22

The Sapphire: Pearl Suite - Peace of mind!

  • 1
  • 4
  • 3 nights min

$139

Details

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ST TROPEZ... amazing views of Heineken Regatta from this beautiful villa in

  • 3
  • 6
  • Min stay varies

$500

Details

1 / 45

RIVIERA... 3 BR hillside villa in Pelican Key, St Maarten

  • 3
  • 6
  • Min stay varies

$358

Details

1
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Provence at Pelican Key, Saint Maarten - Ocean View, Pool, Lovely Outdoor

  • 6
  • 12
  • Min stay varies

$643

Details

2
1 / 18

Anchorage Apartment

  • 1
  • 4
  • Min stay varies

$139

Details

1 / 9

Coco Beach #5 ON THE BEACH

  • 2
  • 6
  • 1 night min

$372

Details

1 / 41

The Reef at Simpson Bay, Saint Maarten - Private Pool, Ocean Views, Modern

  • 5
  • 10
  • Min stay varies

$1143

Details

1 / 10

Great Romantic Condo

  • 1
  • 3
  • 5 nights min

$140

Details

1 / 35

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

  • 5
  • 10
  • Min stay varies

$429

Details

5
1 / 17

Perfect Pelican Escape -- Spectacular Views & Best Sunset Happy Hour

  • 2
  • 4
  • Min stay varies

$125

Details

2
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Villa Balaclava - Luxury villa " MAGNIFIQUE & Full Privacy "

  • 5
  • 10
  • Min stay varies

$515

Details

1
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CARIBBEAN BLUE... 5BR beachfront home in Pelican Key

  • 5
  • 10
  • Min stay varies

$643

Details

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LA DI DA...St Maarten villa high atop a mountain at the mouth of Pelican Key

  • 6
  • 12
  • Min stay varies

$500

Details

2
1 / 23

CASA DE BELLA (formally known as CASELLA)...beautifully furnished, lots of

  • 3
  • 6
  • Min stay varies

$279

Details

1 / 11

Colony Manor

  • 1
  • 2
  • Min stay varies

$200

Details

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Beach Front Property - Amazing Sunset

  • 5
  • 12
  • Min stay varies

$700

Details

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2 Bedrooms 2 Bathrooms Cliffside Villa - Bay Views

  • 2
  • 4
  • Min stay varies

$280

Details

1 / 23

Villa La-Di-Da at Pelican Key, Saint Maarten - Spectacular Ocean View, Infinity

  • 6
  • 12
  • Min stay varies

$857

Details

1
1 / 28

SMART VILLA...nestled beachfront at Pelican Key

  • 3
  • 6
  • Min stay varies

$258

Details

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Steps to Caribbean, pool and 2 mile-long beach

  • 1
  • 2
  • 7 nights min

$225

Details

3
1 / 33

Villa Vita on the beach St Maarten,Caribbean

  • 3
  • 6
  • Min stay varies

$495

Details

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PROVENCE... affordable 6BR villa w/ gorgeous views, close to lots of dining

  • 6
  • 12
  • Min stay varies

$572

Details

1 / 9

Beachfront Condo

  • 2
  • 4
  • 5 nights min

$515

Details

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Villa La Di Da 4 Bedroom SPECIAL OFFER

  • 4
  • 8
  • Min stay varies

$643

Details

1 / 17

Modern Luxury Directly on the Beach

  • 2
  • 4
  • Min stay varies

$250

Details

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Barefoot Oceanfront Condo St Maarten

  • 2
  • 6
  • 4 nights min

$305

Details

1 / 22

Tropical Paradise Villa at Coral Shores in Pelican

  • 2
  • 4
  • 5 nights min

$234

Details

1 / 23

5 Bed 5 Bathrooms Beach Front - Spectacular Sunset

  • 5
  • 12
  • Min stay varies

$700

Details

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