Simpson Bay Beach Rentals

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42 Houses

Dawn Beach Resort, Westin Penthouse for 8 Guests!

Oyster Pond penthouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Games room

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Price per night from

$491

3 bedroom Lux apartment in Dawn beach Club with private beach and infinity pool

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Games room

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Price per night from

$410

Orient Beach Luxury Villa Belle Mer

Orient Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“The most wonderful time of the year!” Our family vacation in St. Martin ended in august, after our 6th year being guests at Villa Belle Mer. Now we are counting the days until next summer to return to the beautiful Island and our second home, Villa Belle Mer. Upon each return new and wonderful things happen at the villa, this year all new outdoor furniture, spacious area for 8 - 10 persons to sit in comfort. I was the queen in the gourmet kitchen until the arrival of a large weber gasgrill, then the men took over cooking the dinners. Our boys spent hours with friends in the upstairs library, playing one of the many games available for the guests, as well about 200 books. The friendly cross breezes and ceiling fans makes this a wonderful get away with the views over to St. Barts. Thank you for letting us share your Villa.

Match: Games room

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Price per night from

$967

Alegria Villa: Barefoot elegant luxury villa with effortless beach access

Blowing Point villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Games room

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Price per night from

$1,653

Large Time Share Rental

Philipsburg condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Games room

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Price per night from

$590

AMANDARA... 20% OFF Apr, May, Jun 2024, Breathtaking Views, Heated Pool! Wow!!

Terres Basses house

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 10

Match: Games room

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Price per night from

$2,234

Dream Villa - 5 bedrooms - Magnificent infinity pool - sea view

Cul de Sac villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Games room

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Price per night from

$788

Suite 5* 3 BD 2 BA Westin Dawn Beach Sint Maarten res. saturday to saturday

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Games room

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Price per night from

$863

VENEZ PROFITER D'UN SEJOUR INOUBLIABLE

Dawn Beach apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Games room

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Price per night from

$431

Your Paradise Villa

Orient Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Games room

All filters match

Price per night from

$638

Dream Villa - 3 bedrooms - Magnificent infinity pool - sea view

Cul de Sac villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Games room

All filters match

Price per night from

$640

Dream Villa - 2 bedrooms - Magnificent infinity pool - sea view

Cul de Sac villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Games room

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Price per night from

$579

Dream Villa - 1 bedroom - Magnificent pool - sea view

Cul de Sac villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Match: Games room

All filters match

Price per night from

$517

West Indies Luxurious Suite SPA 5* (8 pax) St Maarten front of St Barth island

Oyster Pond apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Games room

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Price per night from

$238

Deluxe Studio, Sea view, Jacuzzi

Cupecoy Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Games room

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Price per night from

$386

Stunning Studio at Oyster Pond near Dawn Beach

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Games room

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Price per night from

$154

Ocean View Studio w/ WiFi, Beach Access, Resort Pool & More!

Simpson Bay studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

Match: Games room

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Price per night from

$243

Oyster Pond w Gym & Pool. Explore Your Destination

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Games room

All filters match

Price per night from

$154

VILLA PLUMERIA... PAY for 5 NTS STAY for 7 NTS!!! Heated Pool, Gym & Rec Room!

Terres Basses villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Games room

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Price per night from

$917

Original Studio with Balcony at Oyster Pond

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Games room

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: Games room

All filters match

Price per night from

$154

LE REVE... Spectacular Beachfront Estate, Luxurious Amenities, Chef Included!

Terres Basses villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 13

Match: Games room

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Price per night from

$6,441

Luxury 4 Bedroom, 7 Bathroom Villa on Shoal Bay, Anguilla

Shoal Bay Village villa

  • 4 bedrooms
  • 7 bathrooms
  • sleeps 10

Match: Games room

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Price per night from

$1,606

LA ROSE DU DSERT... Lovely, comfortable villa at a very competitive price!

Terres Basses villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Games room

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Price per night from

$937

Comfy Studio w/ WiFi, Beach Access, Resort Pool & More!

Simpson Bay studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

Match: Games room

All filters match

Price per night from

$234

Match: Games room

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Price per night from

$1,795

Cozy Condo w/ Beach Access, Resort Pool, WiFi & More!

Cole Bay house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

Match: Games room

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Price per night from

$253

CARIBBEAN STONE... Let the FUN begin! Family Villa with Pool, Jacuzzi, Disco!

Terres Basses villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Games room

All filters match

Price per night from

$1,074

ESCAPADE... Amazing Views, Total Privacy, Cool Vibe on the Lagoon!

Terres Basses villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Games room

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Price per night from

$922

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: Games room

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: Games room

All filters match

Price per night from

$154

BRAND NEW 3 BEDROOM OCEANFRONT CONDO!

Oyster Pond condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Games room

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Price per night from

$320

Ideal Family Vacation at Oyster Pond: Beach & Pool

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Games room

All filters match

Price per night from

$154

Villa Francais

Pelican Key villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Games room

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Price per night from

$859

Escape to paradise at Oyster Bay Beach Resort

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 15 minutes

Match: Games room

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: Games room

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: Games room

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: Games room

All filters match

Price per night from

$154

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rentals in Simpson Bay Beach

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