Vacation Rentals & Villas in Simpson Bay

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BEACHFRONTBLISS

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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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

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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

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

$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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$230

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$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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$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

$430

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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Price per night from

$443

Beach Heaven

Simpson Bay penthouse

  • 2 bedrooms
  • 6 bathrooms
  • sleeps 4

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Price per night from

$345

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

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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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$631

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$358

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

Simpson Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$1,682

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

Coco Beach Duplex

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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$262

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Price per night from

$1,276

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

$558

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

Great rentals within 20 miles that match your search

Butterfly

Terres Basses villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$902

Now

Terres Basses villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,041

My friends

Terres Basses villa

  • 14 bedrooms
  • 15 bathrooms
  • sleeps 28

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Price per night from

$5,010

The Blue Palms

St Martin / St Maarten villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$1,288

Tichka (TCK)

St. Barthelemy villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$1,933

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

Island Harbour apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$161

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$645

Dreamcatcher - luxury villa, stunning views over turquoise seas

Shoal Bay Village villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$947

LIFE IN BLUE ... Stunning New 2 BR Luxury Beach Front Villa on Baie Rouge

Terres Basses house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Totally awesome” We stayed a Le Vie En Bleu for 10 days this last July on the advice from Ted at St. Martin Reservation Center. From the moment we stepped into this wonderful villa, we knew Ted's advice was spot on. Everything about this classy home was done with the vacationers enjoyment in mind. Granted, it's a bit small but the floor plan is designed in a way that brought your every glance to the beautiful ocean right in front of you. It had all the modern amenities you'd expect to find in a five star villa rental. My wife used the oceanfront gym each morning and loved it.I could write a novel about this totally private get away in paradise but I'll just say one thing. We plan on returning next summer to Le Vie En Bleu. Thank you Ted !!!

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Price per night from

$1,503

Viewing 38 of 552
rentals in Simpson Bay

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