Windward Rentals

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179 Houses

❤ BelAmour - Luxurious & Romantic Villa for 2 ❤

Pointe Milou villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Match: Sea view

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Price per night from

$1,145

Great rentals within 20 miles that match your search

Studio design bord de mer vue imprenable

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

Match: Sea view

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Price per night from

$135

Orient beach Premium view Frontsea Studio

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 4

Match: Sea view

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Price per night from

$100

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

Anse Marcel villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

Match: Sea view

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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

Match: Sea view

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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

Match: Sea view

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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.

Match: Sea view

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Price per night from

$225

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

Simpson Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$500

Match: Sea view

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Price per night from

$350

BELLA VITA... Stunning Super Deluxe 7BR, Breathtaking Views, Heated Pool!

Simpson Bay villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

Match: Sea view

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Price per night from

$2,800

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

Oyster Pond villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Sea view

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Price per night from

$215

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

Oyster Pond villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$595

Match: Sea view

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Price per night from

$1,300

CARIBBEAN BLUE... 5BR beachfront home in Pelican Key

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Sea view

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Price per night from

$915

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!

Match: Sea view

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Price per night from

$800

Match: Sea view

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Price per night from

$671

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

Orient Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Sea view

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Price per night from

$986

MARISOL... Light and airy townhouse at Point Blue in Pelican Key Estate

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Sea view

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Price per night from

$229

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

Oyster Pond villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Sea view

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Price per night from

$475

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

Match: Sea view

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Price per night from

$1,143

IL PUNTO BLUE...Located right on the beach in prestigious Pelican Key

Simpson Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$429

Match: Sea view

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Price per night from

$515

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

Oyster Pond house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$503

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

Oyster Pond villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Sea view

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Price per night from

$1,329

CASA DE BELLA... Great location at a great price!!

Simpson Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$215

MACASSI 4... Sooo Cute & Affordable!! Walk To Orient Beach!

Orient Bay apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$268

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 ???? ????????? ??????????. ? ???????? ????? ???? ? ????????,?????????????? ? ?????????. ?????? ????? ? ?????? ???????????, ?? ??????? ?????????? ????? ?????? ? ????????.

Match: Sea view

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Price per night from

$457

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

Orient Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Sea view

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Price per night from

$920

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Price per night from

$472

ORIENT SUNRISE... Amazing Views of Orient Bay From This Contemporary Villa

Orient Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$700

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Price per night from

$488

COSTA TURQUOISE... charming, very affordable, directly ON BEACH!

Orient Bay condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Sea view

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Price per night from

$144

VILLA SKY BLUE... Luxurious 5BR ocean view villa - fabulous water views

Oyster Pond house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Sea view

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Price per night from

$856

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Price per night from

$357

Gorgeous Beachfront Villa#9 at 'Villas on Great Bay'

Philipsburg apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view

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Price per night from

$385

MYSTIQUE - LUXURY VILLA AT THE HEART OF THE ISLAND 5B

St. Jean villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Sea view

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Price per night from

$3,516

DAWN BEACH CLUB ST. MAARTEN 3 BEDROOM CONDO

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Sea view

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Price per night from

$654

1 or 2 weeks in condo 5 * St. Marteen seaview

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Sea view

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Price per night from

$210

Viewing 38 of 179
rentals in Windward

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