Simpson Bay Beach Rentals

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95 Houses

Mangrove Villa at Indigo Reef

The Valley villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Responds fast! avg. 42 minutes

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Price per night from

$1,259

Sapphire Ruby Suite - Unforgettable Getaway!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$212

Shrimpys Hostel and Crew Quarters

Marigot b&b

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$68

DAWN BEACH CLUB ST. MAARTEN 3 BEDROOM CONDO

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$655

Grand Case Beach, fully renovated

Grand Case apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$350

The Sapphire: Pearl Suite - Peace of mind!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$197

MES AMIS...Spectacular Ultra Deluxe cliffside masterpiece! Breathtaking views! A

Terres Basses villa

  • 14 bedrooms
  • 13 bathrooms
  • sleeps 26

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Price per night from

$5,010

Villa MOJITO, charming 2 bedrooms, steps from the beach, private pool

Orient Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$311

Oceana Villa Anguilla - Private Panoramic View with Heated Pool

The Valley villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

“Just a very lovely clean home - nothing you will find to complai” We just stayed there for 10 nights for our honeymoon and it was very lovely. So many nice details around the house, very clean, nothing seems to be old or used too much. Everything you will need .. you will find it there. We used the kitchen for breakfast, lunch and dinner. There is a supermarket with a 7 min. drive - you will find everything there. Our favorite beach was at Cap Juluca hotel - it is approx. 20-25 min drive by car. The view from the house is beautiful. If this was not our honeymoon, we would have loved to bring frieds as this house is really big for two. Shelah came about every other day to clean the whole house, put new towels and clean sheets. She did a really good job - nothing to complain about. She also took care of our laundry once and helped us with a trip to Sandy Island. We had a chef one night cooking delicious crayfish - he knew where to find everything. It was a great evening. If you have any questions, you can contact me! Too sad I have to write this review now as it means that this wonderful vacation is over already :-( but I loved every minute of it! Will never forget it and hopefully come back one day!

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Price per night from

$517

Villa Kai

Sandy Hill Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$916

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

Philipsburg apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$386

Sea Side Paradise, Charming 2 bedrooms duplex, beach front, ocean view, pool

Orient Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$311

Coconut Palm Villa -Twin Palms Villas at Meads Bay

Long Bay Village villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$1,661

Orient beach Premium view Frontsea Studio

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 4

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Price per night from

$100

3BDRM Beautiful Condo at Westin Dawn Beach Club

Philipsburg condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$615

Beach Palm Villa - Twin Palms Villas at Meads Bay

Long Bay Village villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$1,025

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

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$410

Enchanting, Family Friendly 3bdr, adjustable fee for more or less bedrooms

East End Village house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 11

Responds fast! avg. 1 hour 43 minutes

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Price per night from

$1,262

Twin Palms Villas at Meads Bay

Long Bay Village villa

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 10

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Price per night from

$1,661

Westin Dawn Beach Resort & Spa

Philipsburg condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$493

C EST LA VIE... WOW!! Spectacular Beachfront Estate, Heated Pool, Chef!

Terres Basses house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$5,572

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Price per night from

$311

Three Dolphins Lockrum Bay, Anguilla BWI

Little Harbour villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

“Wife's Birthday getaway” After extensive research into renting a property in the islands we found Three Dolphins. Since the trip was for my wife and myself as well as two other couples, the villa was the perfect size. The quality of the villa, the location and the service, not just the staff, but the owner herself was beyond our expectations. The house is spectacular as are the surrounding gardens and grounds. The owner assisted us in procuring a rental car which was waiting for us when we arrived at the villa. Since we arrived late in the day they also, by prior arrangement, helped to have some light provisions in the fridge for our arrival. We will be returning.

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Price per night from

$2,295

LE CHATEAU DES PALMIERS... Consider Yourself Royalty at this Beachfront Estate!

Terres Basses villa

  • 10 bedrooms
  • 13 bathrooms
  • sleeps 20

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Price per night from

$6,441

The Embellie Villa and Cottage

The Valley villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

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Price per night from

$114,715

ALWAYS... Hillside 6 BR luxury villa in Terres Basses -

Terres Basses house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$1,400

Gardenia Villa at Indigo Reef

The Valley villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 42 minutes

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Price per night from

$373

LA BELLA CASA... 12BR luxury villa in Terres Basses, St Martin

Terres Basses house

  • 9 bedrooms
  • 12 bathrooms
  • sleeps 24

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Price per night from

$2,792

Dream side, gorgeous 1 bedroom duplex 1st line ocean front

Orient Bay apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$212

SANDYLINE... The Essence of Luxury! 2 Heated Pools, Jacuzzi, Tennis, Gym, Chef!

Terres Basses villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

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Price per night from

$5,224

The Sapphire: Turquoise Suite - Tranquility!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$212

Sea Side Paradise, Charming 1 bedroom duplex, beach front, ocean view, pool

Orient Bay apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$247

NEW CONSTRUCTION -OCEANFRONT PROPERTY - 3 KING BEDROOMS - SLEEPS 8

Dawn Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$493

Round Rock Estate In Anguilla

Blowing Point villa

  • 6 bedrooms
  • 9 bathrooms
  • sleeps 12

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Price per night from

$2,983

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Price per night from

$137

EL Zafiro: Emerald Suite - A Gem within a Gem!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$390

6 Bedroom Luxury Ocean Front Elegant Modern Luxury Villa

Philipsburg villa

  • 6 bedrooms
  • 9 bathrooms
  • sleeps 14

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Price per night from

$3,442

Spectacular St.Maarten Oceanfront Penthouse Condo Private Pool//Roofdeck, OBBR

Oyster Pond condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$517

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