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221 Houses

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❤ BelAmour - Luxurious & Romantic Villa for 2 ❤

Pointe Milou villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$1,145

Great rentals within 20 miles that match your search

NEW LISTING Anse Marcel Beach

Anse Marcel townhouse

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$155

VILLA TINTAMARE, 3 bedrooms, private pool and sea view!!!

Orient Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$628

VILLA GOYAVE, beautiful villa with 2 bedrooms, pool and amazing views!

Orient Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$554

On the famous Orient Bay Beach - garden level 4p

Orient Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$314

POINT OF VIEW... Charming, Affordable 3BR Villa in Orient Bay with Views!

Orient Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$432

KOKOMO... Super Nice Modern Condo! Pool, Short Walk to Oreint Beach!

Orient Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$227

VILLA NUMA... very, Very, VERY COOL 6BR in Beautiful Indigo Bay, St Maarten!

Little Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$1,699

LODGE POUR 2 PERSONNES AVEC PISCINE PRIVEE

Orient Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$191

Infinity Views Villa SXM

Simpson Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$195

Immaculate 1-Bed Apartment in Sint Maarten

Pointe Blanche apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$169

Villa Francais

Pelican Key villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$857

Seagrape, new 3 bedroom townhouse, private pool, steps to beach

Orient Bay townhouse

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

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$344

LAS BRISAS VILLA... Directly waterfront, private pool, very modern

Cole Bay condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$640

GRENOUILLE... Gorgeous Modern Villa in Orient Bay w/ Heated Pool!

Orient Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$750

OCEANS ONE... Sleek, Modern, Very Cool Villa with Heated Pool & Ocean Views

Orient Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$797

VILLA KANOA... Luxurious, Modern, Heated Pool & Gym!

Upper Prince's Quarter villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$629

Blue Door Villa and Little Blue Villa

Philipsburg villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$212

Luxury Luxury Rentals

Philipsburg villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,944

LA MAISON LILE... Affordable, Comfortable Family Villa, Great Ocean Views!

Oyster Pond villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$715

SABA BRISE... Charming, Tropical, Modern Villa in Picturesque Anse Marcel

Anse Marcel villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$685

Very Private Villa with Awesome Views overlooking Simpson Bay

Cole Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$795

SPINNAKER 1322... Oceanfront at Oyster Bay Beach Resort, Dawn Beach

Oyster Pond condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$250

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Price per night from

$234

BRIGHT WATERS... Romantic, Luxurious, Affordable!! Perfect for 2 Couples!

Oyster Pond villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$400

ALIZEA... Chic, Modern 4BR with Stunning Views of Oyster Pond and Dawn Beach!

Oyster Pond villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$475

AQUA DREAM... Amazingly Gorgeous, Modern 6BR Villa in Indigo Bay

Little Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$2,099

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Price per night from

$286

CHEZ MARTINE... Charming Oceanfront Villa with dock and Kayaks!

Cul de Sac villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$504

Appartement Orient Bay-Ti Paradise

Orient Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$154

Stunning 2 bedroom View condo in Maho

Dutch Cul de Sac apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$320

AQUA VISTA... Stunning Modern Oceanfront 6 Bedroom Villa in Indigo Bay

Little Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$2,096

LA CASA DEL JEFE... Modern, Great Views, Close to Orient Bay & Grand Case!

Orient Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$674

Superbe Appartement Villa avec Terrasse et Jacuzzi privé à Orient Baie

Orient Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$160

Modern 2br/2bath cottage in Dawn Beach area at discounted rate

Oyster Pond house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$137

Searulean, a stylish 3 bedroom abode in Orient Bay, steps to beach, private pool

Orient Bay townhouse

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

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Price per night from

$343

On the famous Orient bay Beach, condo 4p

Orient Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$314

Lot 4 Le Clos de lAnse Anse Marcel

Cul de Sac house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$338

Viewing 38 of 221
rentals in Windward

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