Windward Rentals

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442 Houses

❤ BelAmour - Luxurious & Romantic Villa for 2 ❤

Pointe Milou villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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$1,142

Great rentals within 20 miles that match your search

1 Bdrm Condo with Superlative Views of St. Barts

Philipsburg apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

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$229

Beautiful beachfront at The Villas On Great Bay

Philipsburg villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

“Super holiday at the Great Bay” Unfortunatly we have left Villa nr 2 past sunday after 12 wonderfull days! After the confirmation of our reservation we have never had a single doubt on this piece of heaven on earth, but it even exceeded all expectations!! Verry happy to stay here once more and already looking forward to that. This place is relaxing but has all comforts of a fully equiped villa on the other hand as well. Both Jim and Gina (on-site managers) do their very best to make the stay as comfortable as possible.

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$257

Villa Angelina Amazing Panoramic Views

Oyster Pond villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$318

Luxury Villa with private heated pool and AC in all bedrooms

St Martin / St Maarten villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

“If you are looking for a little piece of paradise Twin Palms is” Twin Palms is a modern villa with large immaculate rooms and a gorgeous view. The large kitchen is very well equipped. The patio is huge with lounges that are so comfortable one hates to leave, and then there is the infinity pool. The friendly maid keeps the place spotless. Our family of five adults filing this villa the ultimate place to relax. It was a home away from home.

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$489

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

St. Jean villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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$3,505

SUNRISE - LUXURY VILLA AT THE HEART OF THE ISLAND

St. Jean villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$2,985

Spacious Private Villa, Ocean Views, Concierge

Oyster Pond house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$490

HOUSE SOLD - PLEASE REMOVE

St Martin / St Maarten house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 2

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Price per night from

$245

Studio in Pelican Key Paradise

Simpson Bay apartment

  • 1 bathroom
  • sleeps 2

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Price per night from

$172

Orient Bay cute private villa, naturist are welcome

Orient Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 58 minutes

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$320

Beautiful Condo for rent in St-Martin / Beautiful condo for rent in St-Martin

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$571

MYSTIQUE SUN - 9 BDRS

St. Jean villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 18

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$7,077

On Island Time: Privacy, Luxury, & Stunning Vistas

St Martin / St Maarten villa

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

“Modern Oasis” This is a beautiful modern house with all of the amenities. The main 2-story living space has a glass wall that opens onto the outdoor terrace and yard. The infinity pool looks out over the ocean and lush green valley. We kept the doors open most of the time so that it really felt like the outdoor areas were part of the living room. The kitchen is well equipped and was perfect for the six of us staying in the house. We enjoyed it so much that we are going back this winter...

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$628

VILLA MANGO SEA VIEW, VERY PRIVATE,

Anse de Lorient villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Private, amazing views, wonderful holiday!” My Fiance and I stayed at the Villa Mango during the March/April Spring Break in 2012. We loved the Villa Mango it was perfect for one or two couples. It is so private and relaxing, I can't describe the experience better than saying - worry free, and idealic. Margali and Loulou are the sweetest hosts, and the Villa is everything you will need and hope for. It is clean, comfortable and with every amenity to either stay in and cook or just spend your days relaxing. The pool is warm and refreshing and the hottub perfect for evenings. The owners have really thought of everything!! We can't wait to go back. Having a car rental is a must as you have to drive around and experience the fabulous beaches, markets and yummy bakeries!!

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Price per night from

$683

VistaRoyale - Private pool and breathtaking view

Philipsburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Amazing view !!” This is our tenth year staying at VistaRoyale and we don't want to go anywhere else. It has to be one of the most spectacular views on the planet. Every morning you wake up to arriving cruise ships, beautiful rainbows after a morning shower, the brilliant color of the waters in the bay. And your own private infinity pool, veranda and palm tree. New cabinets, appliances and countertop this year really upgraded the kitchen. It is a perfect property to get away, relax, and unwind. The new owners are easy to deal with and very accessible. Can't wait to return!

Responds fast! avg. 1 hour 18 minutes

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$257

Orient Beach Luxury Villa Belle Mer

Orient Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Sumptuous Luxury!” We spent a glorious week in February, 2010 at Villa Belle Mer. It couldn't have been more wonderful. The house is beautiful and well appointed with all the luxuries you would expect from a villa of this caliber. The bedrooms were beautiful. The pool and patio area was perfection and the within easy walking distance location to Orient Beach cannot be matched. The private french chef we hired created the most delicious meals for us on several evenings of our visit. The daily housekeeper took excellent care of us! We can't wait to return.

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$963

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$702

Ocean front "colibris" amazing view

Marigot, Saint Martin villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$379

1 Bed Luxury Condo

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

Villa Moorea Saint-Barthelemy

Marigot house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$491

THE ROCK 1 New Seaview Duplex Condo with Jacuzzi !

Orient Bay apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 36 minutes

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Price per night from

$187

THE ROCK 2 New Seaview Duplex Condo with Jacuzzi !

Orient Bay apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 36 minutes

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Price per night from

$187

TAK

Colombier villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$1,210

Panoramic Ocean View Condo on Orient Bay

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 3

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$137

Beachfront Villa Lavinia #9

Philipsburg villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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$229

Creole deilght

Orient Bay bungalow

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$160

Villa Le Roc Saint Barthélemy

Petit Cul de Sac villa

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 6

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VILLA BE SXM 180° SEA VIEW , 3 BEDROOMS, SLEEPS 7

Cul de Sac villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$546

VENEZ PROFITER D'UN SEJOUR INOUBLIABLE

Dawn Beach apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$435

Soleil Blanc, gorgeous 1 bedroom villa with private pool

Orient Bay villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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$261

Villa Flagrantia

Philipsburg house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$223

MYSTIQUE - LUXURY VILLA AT THE HEART OF THE ISLAND- 2B

St. Jean villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$2,922

MYSTIQUE - LUXURY VILLA AT THE HEART OF THE ISLAND 4B

St. Jean villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$3,510

Sabrina’s Caribbean Keys # 2

Quartier D'Orleans apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$75

Caribbean dream, Princess Heights Hotel, Dawn Beach, Oyster Pond, St. Maarten

Oyster Pond apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

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Price per night from

$149

Paradise Rock

Oyster Pond villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$236

Mi casa es tu casa appartament next Orient Bay

Orient Bay house

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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Price per night from

$87

Viewing 38 of 442
rentals in Windward

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