Vacation Rentals & Villas in Simpson Bay

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Sapphire Ruby Suite - Unforgettable Getaway!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children under 5

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Price per night from

$212

BEACHFRONTBLISS

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Children under 5

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Price per night from

$345

TARA... Affordable oceanfront villa, walk to beach

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Children under 5

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Price per night from

$660

The Sapphire: Pearl Suite - Peace of mind!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children under 5

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Price per night from

$197

The Sapphire: Aquamarine Suite- Breathtaking views!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children under 5

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Price per night from

$212

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

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Children under 5

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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

Match: Children under 5

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Price per night from

$915

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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Price per night from

$229

Match: Children under 5

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Price per night from

$559

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

Match: Children under 5

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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

Match: Children under 5

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Price per night from

$316

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Price per night from

$671

1Bedroom in Pelican Key

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Match: Children under 5

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Price per night from

$316

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

Simpson Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Children under 5

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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

$430

The Sapphire: Turquoise Suite - Tranquility!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$212

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

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Children under 5

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Price per night from

$442

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

Popular Beachfront property/ Barefoot in SXM

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$304

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

Match: Children under 5

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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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Price per night from

$273

UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Children under 5

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Price per night from

$509

LUXURIOUS 2 BEDROOM CONDO ON SIMPSON BAY

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$631

Sapphire Suite - Indulgent retreat!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$219

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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

Match: Children under 5

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Price per night from

$566

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

Simpson Bay studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

Match: Children under 5

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Price per night from

$243

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Price per night from

$357

the beacon

Simpson Bay house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Children under 5

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Price per night from

$147

Caribbean Breeze SXM

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Children under 5

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Price per night from

$316

Coco Beach House

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Children under 5

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Price per night from

$446

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

Simpson Bay studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

Match: Children under 5

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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

Match: Children under 5

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Price per night from

$298

Emerald Suite - Cocovaa Beach Resort, Beachfront Private Balcony Suite

Simpson Bay private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Children under 5

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Price per night from

$172

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 12 minutes

Match: Children under 5

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Price per night from

$274

Viewing 38 of 1,100
rentals in Simpson Bay

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