Vacation Rentals & Villas in Simpson Bay

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TARA... Affordable oceanfront villa, walk to beach

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$658

COCO BEACH CLUB #5.... Located on the soft white powdery sand of Simpson Bay be

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$229

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

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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$915

Steps to Caribbean, pool and 2 mile-long beach

Simpson Bay apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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$258

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$558

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

Simpson Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$500

WITENBLAUW... Magical Beach Front Estate on Pelican Key

Simpson Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 17

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Price per night from

$2,429

COCO BEACH CLUB 6...walk out onto the sand of Simpson Bay Beach

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$229

Modern Luxury Directly on the Beach

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 28 minutes

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$315

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$671

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

Simpson Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$215

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

Simpson Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$429

Beach Heaven

Simpson Bay penthouse

  • 2 bedrooms
  • 6 bathrooms
  • sleeps 4

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Price per night from

$344

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

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$390

COLONY MANOR GUEST COTTAGE II... Romantic hideaway right on Simpson Bay Beach!

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$229

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

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$272

UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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$508

LUXURIOUS 2 BEDROOM CONDO ON SIMPSON BAY

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$630

Sapphire Suite - Indulgent retreat!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$219

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$215

Sapphire: Peridot Suite - Iconic Views

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$197

Encanto -2 Bedroom Beachfront Condo in Simpson Bay, Sint Maarten -GORGEOUS VIEW!

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$286

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$357

Beautiful 1-bedroom rental apartment in Simpson Bay

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$315

Coco Beach House

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$446

Villa Ocean Breeze - Private Pool - 2 Masters - Private Courtyard

Simpson Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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$745

SURFSONG... 6BR fall in love again! Breathtaking sunsets, directly on ocean!

Simpson Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

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$1,678

Emerald Suite - Cocovaa Beach Resort, Beachfront Private Balcony Suite

Simpson Bay private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

Infinity Views Villa SXM

Simpson Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$195

BEACH SECRET... Modern 4 BR beauty on Burgeaux Bay, walk to Maho!

Simpson Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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$1,146

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$1,796

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$1,315

Hamaka condo, a beachfront retreat on Simpson Bay Beach

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$229

THE GREAT ESCAPE... Rare 3BR Beachfront on Simpson Bay! Perfect for couples!

Simpson Bay condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$625

C-SCAPE CONDO... Beautiful, Modern, Affordable 2BR Directly on Beach!

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$300

Sunset Villa Beacon Hill Sint Maarten

Simpson Bay villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

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Price per night from

$916

FAJA LOBIE... Completely Updated Beachfront Villa on Burgeoux Bay

Simpson Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$557

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Price per night from

$286

Viewing 38 of 471
rentals in Simpson Bay

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