Vacation Rentals & Villas in Simpson Bay

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285 villas

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TARA... Affordable oceanfront villa, walk to beach

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Waterfront

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Price per night from

$660

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: Waterfront

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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

$915

Steps to Caribbean, pool and 2 mile-long beach

Simpson Bay apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Match: Waterfront

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Price per night from

$259

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

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Waterfront

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Price per night from

$229

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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

Match: Waterfront

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Price per night from

$500

WITENBLAUW... Magical Beach Front Estate on Pelican Key

Simpson Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 17

Match: Waterfront

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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: Waterfront

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Price per night from

$230

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

Simpson Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Waterfront

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Price per night from

$430

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

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Waterfront

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Price per night from

$442

Beach Heaven

Simpson Bay penthouse

  • 2 bedrooms
  • 6 bathrooms
  • sleeps 4

Match: Waterfront

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Price per night from

$345

Popular Beachfront property/ Barefoot in SXM

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Waterfront

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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

Match: Waterfront

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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: Waterfront

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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

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Price per night from

$215

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

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Price per night from

$357

Beautiful 1-bedroom rental apartment in Simpson Bay

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Waterfront

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Price per night from

$316

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

Simpson Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Waterfront

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Price per night from

$1,682

Beachfront Retreat. Newly renovated modern apartment on the beach side

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Waterfront

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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: Waterfront

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Price per night from

$172

Infinity Views Villa SXM

Simpson Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Waterfront

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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

Match: Waterfront

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Price per night from

$1,149

Coco Beach Duplex

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Waterfront

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Price per night from

$263

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Price per night from

$1,796

Match: Waterfront

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Price per night from

$1,318

Hamaka condo, a beachfront retreat on Simpson Bay Beach

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Waterfront

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Price per night from

$229

Sunset Villa Beacon Hill Sint Maarten

Simpson Bay villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

Match: Waterfront

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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

Match: Waterfront

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Price per night from

$557

Sapphire Suite - Cocovaa Beach Resort

Simpson Bay private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Waterfront

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Price per night from

$138

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

Simpson Bay villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

Match: Waterfront

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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

Match: Waterfront

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Price per night from

$390

Match: Waterfront

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Price per night from

$483

Great rentals within 20 miles that match your search

Studio design bord de mer vue imprenable

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

Match: Waterfront

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Price per night from

$136

Ocean View Apartment at Captain's Ridge (view from every room)

Island Harbour apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Waterfront

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Price per night from

$161

Viewing 38 of 285
rentals in Simpson Bay

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