Windward Rentals

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321 Houses

❤ BelAmour - Luxurious & Romantic Villa for 2 ❤

Pointe Milou villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Match: Heated pool

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Price per night from

$1,145

Great rentals within 20 miles that match your search

GRENOUILLE... Gorgeous Modern Villa in Orient Bay w/ Heated Pool!

Orient Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Heated pool

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Price per night from

$750

OCEANS ONE... Sleek, Modern, Very Cool Villa with Heated Pool & Ocean Views

Orient Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$797

Villa Nagabaaja

Gustavia villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$1,970

Villa avec piscine, idéalement située- 2 chambres

St. Jean villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Heated pool

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Price per night from

$1,169

COME SPEND HOLIDAY SUPER FACING THE SEA

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$529

CONFORTABLE SUITE AT HOSTEL

Oyster Pond hotel apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$617

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

Simpson Bay villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

Match: Heated pool

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Price per night from

$2,800

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

Orient Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Heated pool

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Price per night from

$700

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.

Match: Heated pool

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Price per night from

$490

Beautiful 3 Bedroom Ocean view Condo

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$524

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

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$211

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!!

Match: Heated pool

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Price per night from

$679

Belle Bague - Stunning Sea Views - 4 Bedroom

Colombier villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$2,857

st martin oceanfront condo

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$492

Match: Heated pool

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Price per night from

$705

WITENBLAUW... Magical Beach Front Estate on Pelican Key

Simpson Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 17

Match: Heated pool

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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

Match: Heated pool

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Price per night from

$409

Dawn Beach Club

Oyster Pond condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$654

Spacious Studio at Oyster Bay Beach: Experience it

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Heated pool

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Price per night from

$154

Original Studio with Balcony at Oyster Pond

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Heated pool

All filters match

Price per night from

$154

Escape to paradise at Oyster Bay Beach Resort

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Heated pool

All filters match

Price per night from

$154

Oyster Bay Beach Resort w Pool: Relax & Rejuvenate

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Heated pool

All filters match

Price per night from

$154

Impeccable Studio w Gym and Hot Tub at Oyster Pond

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Heated pool

All filters match

Price per night from

$154

Oyster Pond Cozy Studio w Pool for Weekend Getaway

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Heated pool

All filters match

Price per night from

$154

Oyster Pond near Dawn Beach: Escape to Paradise

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Heated pool

All filters match

Price per night from

$154

Cozy Studio w Balcony in Oyster Bay Beach Resort

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Heated pool

All filters match

Price per night from

$154

Oyster Bay Beach Resort w Pool and Gym: Enjoy it

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Heated pool

All filters match

Price per night from

$154

Stunning Studio at Oyster Pond near Dawn Beach

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Heated pool

All filters match

Price per night from

$154

Oyster Pond Ideal Studio w Balcony: Unwind & Relax

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Heated pool

All filters match

Price per night from

$154

Oyster Pond Ideal Studio w Balcony. Enjoy Your Day

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Heated pool

All filters match

Price per night from

$154

Oyster Pond w Gym & Pool. Explore Your Destination

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Heated pool

All filters match

Price per night from

$154

Ideal Family Vacation at Oyster Pond: Beach & Pool

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Heated pool

All filters match

Price per night from

$154

Magnificent Studio with Hot Tub at Oyster Pond

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Heated pool

All filters match

Price per night from

$154

Villa Le Roc Saint Barthélemy

Petit Cul de Sac villa

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 6

Match: Heated pool

All filters match

Price per night from

Inquire for Rates

Suite sea view Condo Westin St Martin

Oyster Pond condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Heated pool

All filters match

Price per night from

$177

VENEZ PROFITER D'UN SEJOUR INOUBLIABLE

Dawn Beach apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Heated pool

All filters match

Price per night from

$432

VILLA MAPAI... Stunning oceanfront home, heated pool, full AC, kayaks!

Cul de Sac house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Heated pool

All filters match

Price per night from

$2,000

Viewing 38 of 321
rentals in Windward

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