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

$660

1 Bed Luxury Condo

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

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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Price per night from

$230

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

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$917

Studio in Pelican Key Paradise

Simpson Bay apartment

  • 1 bathroom
  • sleeps 2

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Price per night from

$172

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Price per night from

$559

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

Simpson Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$501

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

$2,434

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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Price per night from

$230

Modern Luxury Directly on the Beach

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 28 minutes

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Price per night from

$316

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Price per night from

$673

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

Simpson Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$216

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

$431

Beach Heaven

Simpson Bay penthouse

  • 2 bedrooms
  • 6 bathrooms
  • sleeps 4

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Price per night from

$345

Popular Beachfront property/ Barefoot in SXM

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$304

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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Price per night from

$230

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

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$273

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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Price per night from

$286

Ocean View Studio w/ WiFi, Beach Access, Resort Pool & More!

Simpson Bay studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

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Price per night from

$243

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Price per night from

$358

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

$316

Coco Beach House

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$447

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

Simpson Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$746

Comfy Studio w/ WiFi, Beach Access, Resort Pool & More!

Simpson Bay studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

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Price per night from

$234

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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Price per night from

$1,149

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Price per night from

$1,796

Coco Beach Duplex

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$263

Caribbean Stunner On the Beach w/ Resort Pool & Close to Nightlife!

Simpson Bay house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

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Price per night from

$274

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

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Price per night from

$1,276

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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Price per night from

$559

BELLA VITA... Stunning Super Deluxe 7BR, Breathtaking Views, Heated Pool!

Simpson Bay villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

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Price per night from

$2,806

COCO BEACH HOUSE... Charming refurbished 2BR on Simpson Bay Beach

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$391

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Price per night from

$483

Great rentals within 20 miles that match your search

THE ROCK 1 New Seaview Duplex Condo with Jacuzzi !

Orient Bay apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 32 minutes

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Price per night from

$186

THE ROCK 2 New Seaview Duplex Condo with Jacuzzi !

Orient Bay apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 32 minutes

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Price per night from

$186

Viewing 38 of 624
rentals in Simpson Bay

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