Vacation Rentals & Villas in Simpson Bay

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138 villas

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

Simpson Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Mountain Views

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Price per night from

$501

Match: Mountain Views

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Price per night from

$673

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

Simpson Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Mountain Views

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Price per night from

$216

Beach Heaven

Simpson Bay penthouse

  • 2 bedrooms
  • 6 bathrooms
  • sleeps 4

Match: Mountain Views

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Price per night from

$345

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

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Mountain Views

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Price per night from

$390

Popular Beachfront property/ Barefoot in SXM

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Mountain Views

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Price per night from

$304

Emerald Suite - Cocovaa Beach Resort, Beachfront Private Balcony Suite

Simpson Bay private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Mountain Views

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Price per night from

$172

Infinity Views Villa SXM

Simpson Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Mountain Views

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Price per night from

$195

Match: Mountain Views

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Price per night from

$1,795

Sapphire Suite - Cocovaa Beach Resort

Simpson Bay private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Mountain Views

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Price per night from

$138

Hamaka condo, a beachfront retreat on Simpson Bay Beach

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Mountain Views

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Price per night from

$229

Great rentals within 20 miles that match your search

AZUR DREAM... 7 BR private, tropical, tranquill... great vacation villa for thos

Terres Basses villa

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Mountain Views

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Price per night from

$1,575

CASA SAND... Gorgeous tropical hideaway! Very private and quiet!

Anse Marcel house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Mountain Views

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Price per night from

$541

FALAISE DES OISEAUX... Perfect for couples, privacy, stunning views!

Terres Basses house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Excellent” Wonderful home for 2-4 people. Excellent staff at house. Close to beach, stores, etc. Views of ocean, island and anquilla are the best. Total privacy within 5 acre property. St Martin Reservation Center are by far the best we have ever dealt with on any vacation. We have rented this property for 9 straight years and Ted and his staff do it all. They arrange for pickup at airport, delivery of rental car to house and make sure our vacation is worry free. They have also recomended new restaurants over the years. Joann, at reservation center recomended this property after I viewed 5 in 2004. Joann guided me to chose this one based on her expierence with the properties. We have not been disapointed. Highly recomend the property and St Martin Reservation Center.

Match: Mountain Views

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Price per night from

$702

CALLISTO... Full AC, lovely sunset views!

Terres Basses house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

“Gorgeous, but do not forget your bug spray.” We absolutely loved Callisto...a gorgeous property that is nicely designed with 3 "Master" bedrooms.Very clean and comfort! Everything was perfect but be forewarned...there are tons of tiny mosquitos and this is open living! The wall of sliders opens the entire villa to the gorgeous outdoor living area and the infinity pool...with spectacular views. I'll book Callisto again. Lovely property.You can't beat this place...just bring your bug spray!

Match: Mountain Views

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Price per night from

$559

SOL E LUNA... Beautifully appointed, comfortable and very priva, huge pool!

Terres Basses house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Mountain Views

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Price per night from

$645

LA NINA... Includes Tennis Court & Gym for 2 lucky couples or small family

Terres Basses villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Mountain Views

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Price per night from

$496

NO LIMIT...3 equal master suites, luxury, views, great for couples!

Terres Basses house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Mountain Views

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Price per night from

$645

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

Terres Basses house

  • 9 bedrooms
  • 12 bathrooms
  • sleeps 24

Match: Mountain Views

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Price per night from

$2,792

CAYE BLANCHE... elegant updated 7BR villa with lovely views

Anse Marcel house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

Match: Mountain Views

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Price per night from

$1,799

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

Anse Marcel villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

Match: Mountain Views

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Price per night from

$3,578

LA SALAMANDRE... Fabulous Waterfront Villa, Private Beach, Heated Pool!

Terres Basses house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Match: Mountain Views

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Price per night from

$1,804

LA JOSEPHINE...6 BR Family Villa... Huge Pool & Outdoor Entertainment Area!

Terres Basses house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Mountain Views

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Price per night from

$1,323

BOUGAINVILLEA...Fabulous views overlooking Dawn Beach & St. Barths

Oyster Pond villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Mountain Views

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Price per night from

$937

BELLE FONTAINE... 5 master suites, huge gazebo, the perfect couples villa!

Terres Basses house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

“Favorite Yearly Family Vacation--St Maarten” Belle Fontaine was great and is perfect for a large family or friends to get together. We spent most of our time in the Pool & Gazebo. The house is large enough that you don't feel crowded and can go off by yourself for some quite time alone. We always felt safe since the villa is in an area that is gated and you could not get in without identification. Thanks to Ted from Odrc, this was another wonderful vacation with exceptional service.

Match: Mountain Views

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Price per night from

$1,133

Lighthouse 3C...Featuring beautiful views of the ocean and Dawn Beach

Oyster Pond farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Mountain Views

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Price per night from

$501

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

Terres Basses villa

  • 14 bedrooms
  • 13 bathrooms
  • sleeps 26

Match: Mountain Views

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Price per night from

$5,010

Match: Mountain Views

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Price per night from

$351

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

Oyster Pond villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Mountain Views

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Price per night from

$597

Match: Mountain Views

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Price per night from

$1,303

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: Mountain Views

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Price per night from

$802

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

Oyster Pond villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Mountain Views

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Price per night from

$476

ALEXINAS DREAM... Lovely villa overlooking pristine Happy Bay Beach!

La Savane villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Mountain Views

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Price per night from

$716

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

Match: Mountain Views

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Price per night from

$1,146

SEACHEST...Spacious, full AC, gorgeous views of Simpson Bay Lagoon

Cupecoy Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Mountain Views

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Price per night from

$674

Match: Mountain Views

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Price per night from

$473

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

Terres Basses house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Mountain Views

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Price per night from

$1,400

SYRIANA... Penthouse in Porto Cupecoy, ocean, marina & lagoon views from private

Cupecoy Bay apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Mountain Views

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Price per night from

$401

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rentals in Simpson Bay

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