Simpson Bay Rentals with Pools

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757 villas in Simpson Bay with pools

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TARA... Affordable oceanfront villa, walk to beach

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Swimming pool

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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: Swimming pool

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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: Swimming pool

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Price per night from

$918

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

$259

Studio in Pelican Key Paradise

Simpson Bay apartment

  • 1 bathroom
  • sleeps 2

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Price per night from

$173

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

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Swimming pool

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Price per night from

$230

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Price per night from

$560

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

Simpson Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$502

WITENBLAUW... Magical Beach Front Estate on Pelican Key

Simpson Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 17

Match: Swimming pool

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Price per night from

$2,435

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

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Swimming pool

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Price per night from

$230

Match: Swimming pool

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Price per night from

$673

1Bedroom in Pelican Key

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Match: Swimming pool

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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: Swimming pool

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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

Match: Swimming pool

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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: Swimming pool

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Price per night from

$443

Ocean Front with Private Pool

Simpson Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Swimming pool

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Price per night from

$287

Beach Heaven

Simpson Bay penthouse

  • 2 bedrooms
  • 6 bathrooms
  • sleeps 4

Match: Swimming pool

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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: Swimming pool

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Price per night from

$305

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

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Swimming pool

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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: Swimming pool

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Price per night from

$510

Beach view

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$566

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

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$286

Match: Swimming pool

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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

Match: Swimming pool

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Price per night from

$316

Caribbean Breeze SXM

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Swimming pool

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Price per night from

$316

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

Simpson Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Swimming pool

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Price per night from

$746

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

Simpson Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Swimming pool

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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

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Price per night from

$299

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

Simpson Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$1,149

Match: Swimming pool

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Price per night from

$1,800

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Price per night from

$1,318

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

Simpson Bay condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$627

Match: Swimming pool

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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

Match: Swimming pool

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Price per night from

$919

Atrium Beach Resort and Spa 2BR

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$206

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

Simpson Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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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

Match: Swimming pool

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Price per night from

$2,807

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

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Swimming pool

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Price per night from

$391

Viewing 38 of 757
rentals in Simpson Bay

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