Windward Rentals

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562 Houses

❤ BelAmour - Luxurious & Romantic Villa for 2 ❤

Pointe Milou villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$1,148

Great rentals within 20 miles that match your search

1 Bed Luxury Condo

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

Tichka (TCK)

St. Barthelemy villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$1,933

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

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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Price per night from

$410

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

$402

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

$525

Gd studio dans résidence Mont Vernon vue montagne

Orient Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$74

The Source

Marigot, Saint Martin villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$741

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

Dawn Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$493

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

$867

Panoramic Ocean View Condo on Orient Bay

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 3

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Price per night from

$138

COME SPEND HOLIDAY SUPER FACING THE SEA

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$530

3BR 2Bath Gorgeous condo, Fully Equipped

Oyster Pond condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$493

Paradise on Earth!

Cul de Sac villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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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

$938

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

Oyster Pond farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$501

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

Simpson Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$501

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Price per night from

$1,303

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$351

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

$597

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

MANGO... Modern, Full AC, gorgeous views of Orient Bay!

Orient Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$989

FIVE MINUTES MORE... Fabulous contemporary villa overlooking Oyster Pond

Oyster Pond house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Amazing Villa!” 7 of us stayed at this villa. Amazingly clean and the web photos don't do it justice. Re/max did a great job addressing a couple of minor issues. We would definitely stay here again!

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Price per night from

$803

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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$673

“great locations,,, great villa” loved the villa... better than we had hoped for,,,

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Price per night from

$1,147

CORALITA...4 BR casual villa in French St Martin on Oyster Pond

Oyster Pond villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$477

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Price per night from

$799

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

$216

PARADISO... Stunning modern 6 BR villa with huge blue views!!

Oyster Pond villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$1,333

ARCADIA...Charming hillside 3BR villa... wonderful sea & marina views

Oyster Pond house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

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$504

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$516

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

HOPE ESTATE...4 BR Deluxe Villa Overlooking Orient Bay

Orient Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$923

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

$431

BEACH HOUSE YOUNES.. Oceanfront 2BR villa just steps from Dawn Beach

Oyster Pond villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Nice oceanfront villa” ???????? ????? ?? ??? ???? ??? ????? ? ?????? ? ???????? ???????. ???????? ??? ? ???????????? ??? ??????. ???????? ?????????? ? ??????? ??????????. ? ???? ???? ??? ??????????? ???????????? ? ??????????????. ???? Wifi ? ??????? ???????.????????? ???????? ?????? ???? ????? ?? ? ??. ?? ??????? ????? ????????? ???-?? ???????, ??? ?? ? ???????. ?????????? ?? ??????????? ??????? ? 30-40 ??????? ?? ????????? ? ? 10-15 ??????? ?? ??????????? ,???????? ?? ??????????? ???????. ???? Dawn beach ????? ??? ??????, ???? ??????? ??????, ????????? 3 ??????. ?? ?????? ??????? ????? ? OysterPond ???? ????????? ??????????. ? ???????? ????? ???? ? ????????,?????????????? ? ?????????. ?????? ????? ? ?????? ???????????, ?? ??????? ?????????? ????? ?????? ? ????????.

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Price per night from

$458

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Price per night from

$474

Viewing 38 of 562
rentals in Windward

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