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623 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

THE ROCK 1 New Seaview Duplex Condo with Jacuzzi !

Orient Bay apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 32 minutes

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$184

Suite luxueuse Saint-Martin

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$526

Studio design bord de mer vue imprenable

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

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$135

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$643

Premier VRBO & Airbnb Villa ★ Very Private, Breathtaking Views & Serene ★

Oyster Pond villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$808

Orient beach Premium view Frontsea Studio

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 4

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$100

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$705

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

$2,429

3 bedroom Lux apartment in Dawn beach Club with private beach and infinity pool

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$409

Best rated: SXM Panoramic Ocean View private villa w/exclusive private pool.

Philipsburg villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$401

Dawn Beach Club

Oyster Pond condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$654

SUITE 6/8 PEOPLE DAWN BEACH CLUB

Dawn Beach hotel apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$521

Dawn Beach Resort, Westin Penthouse for 8 Guests!

Oyster Pond penthouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$490

Mount Vernon Villas

Cul de Sac apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$298

The Source

Marigot, Saint Martin villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$735

Loue appartement de luxe 6/8 personnes(DBC) refait à neuf .Balcon vue mer.

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$573

TAK

Colombier villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$1,195

NEW CONSTRUCTION -OCEANFRONT PROPERTY - 3 KING BEDROOMS - SLEEPS 8

Dawn Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$492

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$309

Suite 5* 3 BD 2 BA Westin Dawn Beach Sint Maarten res. saturday to saturday

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$860

KARUKERA...4 BR Luxe Villa Over looking Orient Bay

Orient Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,072

Amazing villa 500 m away from the beach for 8 ppl. with swimming-pool

Gustavia villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 50 minutes

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Price per night from

$1,865

Villa Moorea Saint-Barthelemy

Marigot house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$484

Beautiful apartment on St Martin

Oyster Pond apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Paradise on Earth!

Cul de Sac villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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LE PRIVILEGE...Huge 7BR Villa - Stunning Views of Marcel Cove

Anse Marcel villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

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Price per night from

$3,571

BOUGAINVILLEA...Fabulous views overlooking Dawn Beach & St. Barths

Oyster Pond villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$935

TRES CHIC... fabulous modern beachfront condo at Caribbean Riviera on Orient Bay

Orient Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$310

ESTHER... charming, new, affordable townhome with private pool, walk to Orient b

Orient Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect!!” We stayed at Villa Esther just last week. It's in a excellent location with walking access to Bikini Beach as well as La Playa which provides a free chair and umbrella, with drink purchase. The plunge pool is perfect for a cooling down after the beach. Wifi keeps you connected with home without massive cell charges, and the entire place is clean and functional. A/C works great on hot nights. Best part is your walking distance to some of the best cuisine on the island. It's all here at Villa Esther, as well as an outstanding staff to welcome you.

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Price per night from

$225

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

$2,800

Lighthouse 3C...Featuring beautiful views of the ocean and Dawn Beach

Oyster Pond farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$500

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$350

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Price per night from

$1,300

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

$500

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

VICTORIA...3 BR affordable St Martin rental villa, panoramic views

Oyster Pond villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$595

HOPE COTTAGE... charming, romantic hideaway w/ breathtaking views!

Oyster Pond villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$215

Viewing 38 of 623
rentals in Windward

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