Windward Rentals

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259 Houses

❤ BelAmour - Luxurious & Romantic Villa for 2 ❤

Pointe Milou villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$1,141

Great rentals within 20 miles that match your search

COME SPEND HOLIDAY SUPER FACING THE SEA

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$527

The ONLY 5-Star on Dutch side: 3BR, 2BA, Full ktch

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$978

3BR 2Bath Gorgeous condo, Fully Equipped

Oyster Pond condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$490

1 Bed Luxury Condo

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

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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Price per night from

$185

Suite luxueuse Saint-Martin

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$527

Studio design bord de mer vue imprenable

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$135

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Price per night from

$641

Orient beach Premium view Frontsea Studio

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 4

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Price per night from

$100

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

$3,558

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

$932

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

$309

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

$2,790

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

Oyster Pond farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$499

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Price per night from

$349

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

$499

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Price per night from

$1,296

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

$912

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

$593

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

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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$797

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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Price per night from

$229

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

$983

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Price per night from

$669

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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$474

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$513

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$794

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

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Price per night from

$1,139

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

$428

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

Oyster Pond house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$502

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

$456

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

$215

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

$1,324

MATISSE... fully refurbished beachfront on Orient Bay!

Orient Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

“Perfect” My concern about rating this property so well is that we will not be able to find an open week the next time we want to rent. The success of our vacation must be credited to the patient assistance from the St Martin Reservation Center.

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Price per night from

$314

Viewing 38 of 259
rentals in Windward

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