Simpson Bay Beach Rentals

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27 Houses

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studio pinel

Cul de Sac apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$150

CORFU... Penthouse w/ Private Pool at Porto Cupecoy, St Maarten

Cupecoy Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$452

lovely home on the beach

Baie Nettle villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Amazing villa” We had such great time ...No word to describe it: just amazing... the villa was clean, cute as the pictures, we had every thing that we needed. We will recommend it to our family and friend for sure.. We will come back again and again. Thank you for the owner who gave us great advice on where to go... I certainly give it a 5 on 5 ...

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Price per night from

$118

Between lagoon and Caribbean Ocean, large studio

Marigot apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$144

MAEVA... Affordable, modern, completely new after Irma! Steps to beach!

Orient Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$121

MARINA 360......Porto Cupecoy, overlooking Simpson Bay and the Marina, St Maarte

Cupecoy Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$402

AQUA VUE... Rare 4BR at Porto Cupecoy!..Huge Gym, Heated Pool, Tennis Courts, be

Cupecoy Bay apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$517

AGUA AZUL... Gorgeous 2BR at Porto Cupecoy, great location on the Gold Coast!

Cupecoy Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$288

The Embellie Villa and Cottage

The Valley villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

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Price per night from

$114,967

ARTIMINO...3 BR condo, located in Porto Cupecoy, St Maarten

Cupecoy Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$452

VILLA MAPAI... Stunning oceanfront home, heated pool, full AC, kayaks!

Cul de Sac house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$2,009

VILLA ALABASTER ~ LITERALLY BEACHFRONT ON DAWN BEACH w private pool

Oyster Pond villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$719

SYRIANA... Penthouse in Porto Cupecoy, ocean, marina & lagoon views from private

Cupecoy Bay apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$402

BAMBOO... Modern and Romantic, 2 Master Suites, Very Private, Full AC, Jacuzzi!

Terres Basses villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$717

VENEZ PROFITER D'UN SEJOUR INOUBLIABLE

Dawn Beach apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$430

Paradise on Earth!

Cul de Sac villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

Inquire for Rates

West Indies Luxurious Suite SPA 5* (8 pax) St Maarten front of St Barth island

Oyster Pond apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$237

SPINNAKER #1432... Oceanfront at Oyster Bay Beach Resort on Dawn Beach

Oyster Pond condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$251

Private Boat, 40ft Modern Catamaran on on Turquise water

Grand Case boathouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$491

Sand Villa at Long Bay Villas Anguilla: 5-Star Service on a Secluded Beach

Long Bay Village villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$5,174

LES PALMIERS BLEUS... 5BR - Plum Baie beach, Private Tennis, Gym, heated pool!

Terres Basses villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$1,291

Sea Villa at Long Bay Villas on Long Bay Beach. Ultra-Luxury Staffed Villa

Long Bay Village villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 11

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Price per night from

$5,634

LE CAPRICE... Spacious 7BR on Elevated Beachfront Lot, Breathtaking Views!

Terres Basses villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$2,511

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Price per night from

$1,803

LA SAMANNA VILLAS... Private, Luxurious 5 Star Resort Amenities & Service!

Terres Basses villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$4,810

Your all-inclusive one-week private cruise

Grand Case boathouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$1,382

SIVIEW APARTMENT... Sweet beachfront condo on Orient beach

Orient Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$253

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