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

$656

The Sapphire: Aquamarine Suite- Breathtaking views!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$211

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

$229

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

$912

Steps to Caribbean, pool and 2 mile-long beach

Simpson Bay apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$257

Studio in Pelican Key Paradise

Simpson Bay apartment

  • 1 bathroom
  • sleeps 2

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Price per night from

$172

MARISOL... Light and airy townhouse at Point Blue in Pelican Key Estate

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$229

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$556

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

$499

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

$2,420

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

$229

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Price per night from

$669

1Bedroom in Pelican Key

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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Price per night from

$314

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

$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

$428

RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit on a great beach!

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$441

Ocean Front with Private Pool

Simpson Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$286

Beach Heaven

Simpson Bay penthouse

  • 2 bedrooms
  • 6 bathrooms
  • sleeps 4

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Price per night from

$343

Popular Beachfront property/ Barefoot in SXM

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$303

Catamaran - Fully-Crewed & All-Inclusive - St. Martin, Caribbean

Simpson Bay yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$2,000

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

$229

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

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$271

UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$507

LUXURIOUS 2 BEDROOM CONDO ON SIMPSON BAY

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$628

Sapphire Suite - Indulgent retreat!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$218

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Price per night from

$215

Sapphire: Peridot Suite - Iconic Views

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$197

Beach view

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$565

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

$356

the beacon

Simpson Bay house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$146

Caribbean Breeze SXM

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$314

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

Beachfront Retreat. Newly renovated modern apartment on the beach side

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$297

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

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

$623

Atrium Beach Resort and Spa 2BR

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$205

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

$555

Viewing 38 of 989
rentals in Simpson Bay

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