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Simpson Bay Villas

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    Travellers to Simpson Bay are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    86 Matching Rentals in Simpson BayView all 172 rentals
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Beachside is a beautifully decorated 3 bedroom, 3 bath located directly on the beach at Palm Beach Condos, a intimate and well designed gated community of only 24 units, all facing the pool and the beach beyond on the Dutch side of Sint Maarten. The layout was designed to give each unit a...
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    Simpson Bay, Sint Maarten 97700
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    SMART VILLA...nestled beachfront at Pelican Key1 / 29
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    One Free Night (7 nights or more) - Travel from Aug 10 - Dec 15, 2017!Please inquire about lower rates offered for less than full occupancy.Villa Smart is nestled beachfront at Pelican Key and offers a totally tropical, affordable family St. Maarten vacation rental with direct beach access and...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Ocean Views
    • Terrace
    • Balcony
    • Housekeeping Included
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    Pet friendly
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    About this property
    RENTAL 2/11/2017 2/18/2017 Week 6 Simpson Bay Resort Beautiful 1 bedroom with 2 murphy beds comfortably sleeps 4. Newly renovated, in Caladium Building, features King Bedroom with flat screen TV, free internet, large closets, full kitchen with large counter space and full size appliances, dining...
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    Simpson Bay, Sint Maarten NONE
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    About this property
    Welcome to Diamond Hill Estate and Villa Diamond Chateau...This villa offers unparalleled privacy, breathtaking views of Simpson Bay Lagoon, Juliana Airport, the Caribbean Sea and Anguilla in the distance. The villa is at a central location overlooking the Simpson Bay harbor with easy access to...
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    Simpson Bay, Sint Maarten 97700
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    About this property
    Built on a cliff, directly above the tropical blue sea. The Luxury Rental Villa Tara offers vacationers a ‘one of a kind’ experience. The backyard of this home is the majestic Caribbean Sea, and it can be admired from almost every room in this villa. Cleverly designed pocket doors, allow you to...
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    Simpson Bay, Sint Maarten 97700
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Tres Belle Villa1 / 16
    (10)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    We offer privacy in this safe, romantic, Coral Shore setting at the outside edge of Pelican Key, where you are so close to beaches, shopping, restaurants, casinos and water sports activities. Swim, fish, and snorkel right in front of your own villa. Large pool with lounging areas, too. We...
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    Simpson Bay, Sint Maarten 00000
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    WITENBLAUW... Magical Beach Front Estate on Pelican Key1 / 61
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    Witenblauw Estate is a magnificent, sprawling 6 bedroom paradise built for entertaining and relaxation! If a picture is worth a thousand words then Witenblauw speaks volumes when it comes to making memories of a lifetime. This ocean side retreat redefines the traditional get-a-way vacation...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Diamond Hill Estate and Villa Diamond Chateau...This villa offers unparalleled privacy, breathtaking views of Simpson Bay Lagoon, Juliana Airport, the Caribbean Sea and Anguilla in the distance. The villa is at a central location overlooking the Simpson Bay harbor with easy access to...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    6 Bedrooms, 7 Bathrooms, Sleeps 22 Quick View
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    • Air Conditioning
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    • Waterfront
    • Private Outdoor Pool (Unheated)
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    They say a picture is worth a thousand words… That being said, Witenblauw speaks volumes when it comes to making memories of a lifetime. This ocean side paradise redefines the traditional get-a-way vacation experience. This is a true escape from reality into a living fantasy. To experience...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 22
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    They say a picture is worth a thousand words… That being said, Witenblauw speaks volumes when it comes to making memories of a lifetime. This ocean side paradise redefines the traditional get-a-way vacation experience. This is a true escape from reality into a living fantasy. To experience...
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    Simpson Bay, Sint Maarten 97700
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    About this property
    Located over the hill on the sea at Pelican Key, Daffodil is a luxurious,5 bedrooms, 5 bath villa, whose unique glistening cerulean blue tile roof promises a memorable vacation experience. It’s Dutch flavour is showcased by colourful furnishings from international designers, and represents...
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    Simpson Bay, Sint Maarten 97700
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful, Newly remodeled 3 Bedroom, 3 Bath Villa. Breath Taking Views of of the Ocean with an entrance right to the Beach. Very Spacious,with an open floor plan, great for Family and Entertaining groups. Romantic Patio with Jacuzzi and Views of the Sunset Also Make this the Perfect Romantic...
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    Simpson Bay, Sint Maarten N A
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Satellite TV
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please inquire about lower rates offered for less than full occupancy.VILLA BELLA VITA – Where the amenities of a Five-Star Resort luxury meet with the serenity, the privacy and the personalized service that each guest deserves.Named for the “Beautiful Life” it represents, Villa Bella Vita was once...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    Surround yourself with lush tropical gardens and the breathtaking views of the ocean. The large covered terrace overlooks the sparkling oval shaped pool and the beautiful Caribbean Sea. Perfect place for a romantic dinner, cocktails, coffee or just relaxing with a backdrop of aqua waters,...
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    Simpson Bay, Sint Maarten 00000
    Holiday Rental House - 2 Bedrooms, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
    • Wi-Fi
    • Ocean Views
    • Private Outdoor Pool (Unheated)
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    • Satellite TV
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled on the beautiful Burgeaux Bay beach. Villa Sunset is a wonderful, spacious 6 bedrooms 6-bathroom home located in the Beacon Hill area. This beach front property comes with great amenities such as kayaks and paddle boards that will allow its guest to fully enjoy the ocean fun. The bedrooms...
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    Simpson Bay, Sint Maarten 9999 XX
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Beachfront Property - You've discovered a place where piercing turquoise waters meet the deeper blue of the sky, and where elegance meets simplicity, and style meets perfect function. Welcome to Villa Bahari, a luxury Caribbean 3 Bedroom, 3.5 Bathroom villa at Shore Pointe at Cupecoy Beach, on the...
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    Simpson Bay, Sint Maarten 97700
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
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    • Waterfront
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built on 3 levels, the villa’s immaculate interior spaces include a ground floor, well-equipped and welcoming kitchen, a spacious dining area with a long table easily able to seat 10/12 people and an impressive home cinema with seating for 8. The 2nd floor houses 3 large bedroom suites with king...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    LaLuna at Beacon Hill Road, Simpson Bay - Beach Front, Pool1 / 22
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
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    • Shared Outdoor Pool (Unheated)
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Laluna is a beautiful two level property located in the quiet area called Beacon Hill. The villa is composed of 4+1 bedrooms and 5 bathrooms and offers a comfortable and bright interior with large windows and plenty of natural light. The main level consists of an open-plan living area...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Villa Speranza 3 Bedroom (This Three Bedroom Contemporary Villa Is Located On A1 / 61
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Speranza, this three bedroom contemporary villa is located on a hillside facing the Simpson Bay lagoon, and the Dutch side of St. Maarten, with captivating views both day and night. Spend your days poolside on the outside terrace that extends the width of the villa featuring an oversized pool, and...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Internet Access
    • Washer
    • Grill
    • Satellite TV
    • Terrace
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautiful oceanfront 5 bedroom, 4 bathroom property that is located in a nice quiet area of Beacon Hill overlooking Burgeaux Bay on Dutch, St. Maarten.This villa offers amazing colours in the morning and unique sunsets. The villa is located within walking distance to great restaurants...
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    Simpson Bay, Sint Maarten 000
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Villa Amaryllis 2 Bedroom (In A Stunning Waterfront Location On The Simpson Bay1 / 34
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5 Bedroom Villa can be rented as a 2 or 3 Bedroom Villa at special rates! In a stunning waterfront location on the Simpson Bay lagoon, Villa Amaryllis is a luxurious fully air-conditioned, 5 bedroom residence, with its own boat dock and private pool overlooking the lagoon and the French...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    This 6 Bedroom Villa can be rented as a 2, 3, 4 or 5 Bedroom Villa at special rates! La-di-da is a gorgeous, contemporary 4 bedroom, 4 bath villa with a 2 bedroom apartment located below the main part of the villa that sits high atop a hill at the mouth of Pelican Key. This setting provides...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 6 Bathrooms, Sleeps 2 Quick View
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    • Wi-Fi
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    Caribbean Blue is a beach front villa in Pelican Key. With five bedrooms and five and an half bathrooms, it is a perfect house for a family vacation. Caribbean Blue may be rented with use of either 3, 4 or 5 bedrooms. The deck with a private pool at Caribbean Blue is the perfect spot for...
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    Simpson Bay, Sint Maarten 97700
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    This 6 Bedroom Villa can be rented as a 2, 3, 4 or 5 Bedroom Villa at special rates! La-di-da is a gorgeous, contemporary 4 bedroom, 4 bath villa with a 2 bedroom apartment located below the main part of the villa that sits high atop a hill at the mouth of Pelican Key. This setting provides...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Your private bit of heaven in the Caribbean…Just 10 minutes drive from Princess Juliana Airport, Villa Francesca is located in beautiful Pelican Keys and offers the luxury of space and privacy that you can not experience in a hotel…It is your home away from home. Tastefully decorated in...
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    Simpson Bay, Sint Maarten 97700
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Villa Amaryllis 3 Bedroom (Built On 3 Levels Offering Dazzling White Interiors1 / 34
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5 Bedroom Villa can be rented as a 2 or 3 Bedroom Villa at special rates! In a stunning waterfront location on the Simpson Bay lagoon, Villa Amaryllis is a luxurious fully air-conditioned, 5 bedroom residence, with its own boat dock and private pool overlooking the lagoon and the French...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Satellite TV
    • Grill
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    • Private Outdoor Pool (Unheated)
    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Speranza, this three bedroom contemporary villa is located on a hillside facing the Simpson Bay lagoon, and the Dutch side of St. Maarten, with captivating views both day and night. Spend your days poolside on the outside terrace that extends the width of the villa featuring an oversized pool, and...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Air Conditioning
    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One Free Night (7 nights or more) - Travel from Aug 10 - Dec 15, 2017!Please inquire about lower rates offered for less than full occupancy. Villa Provence enjoys a majestic view from its elevated location up on the Pelican Key and offers breathtaking sunsets every evening. Imagine watching the sun...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Satellite TV
    • Parking
    • Balcony
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5 Bedroom Villa can be rented as a 2 or 3 Bedroom Villa at special rates! In a stunning waterfront location on the Simpson Bay lagoon, Villa Amaryllis is a luxurious fully air-conditioned, 5 bedroom residence, with its own boat dock and private pool overlooking the lagoon and the French...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Parking
    • Balcony
    • Washer
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5 Bedroom Villa can be rented as a 2 or 3 Bedroom Villa at special rates! In a stunning waterfront location on the Simpson Bay lagoon, Villa Amaryllis is a luxurious fully air-conditioned, 5 bedroom residence, with its own boat dock and private pool overlooking the lagoon and the French...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Housekeeping Included
    • Waterfront
    • Ocean Views
    • Satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Laluna is a beautiful two level property located in the quiet area called Beacon Hill. The villa is composed of 4+1 bedrooms and 5 bathrooms. This spectacular beach front property offer great morning views with the parade of cruise ships, yachts and sail boats and at night great colorful...
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    Simpson Bay, Sint Maarten 97064
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • Parking
    • Washer
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5 Bedroom Villa can be rented as a 2 or 3 Bedroom Villa at special rates! In a stunning waterfront location on the Simpson Bay lagoon, Villa Amaryllis is a luxurious fully air-conditioned, 5 bedroom residence, with its own boat dock and private pool overlooking the lagoon and the French...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Villa Casa Carib, Luxuary 2 Bedroom/2 Bath on Simpson Bay Beach1 / 19
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Carib, a new spacious 2 bedroom, 2 bath beachfront Villa of 1700 sq. ft. is located directly on one of the most beautiful (2 1/2 mile ) beaches found anywhere in the Caribbean. Often referred to as the “best kept secret” on the island, Simpson Bay Beach is truly a “jewel” amongst St. Maarten’s...
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    Location Information
    Simpson Bay, Sint Maarten N A
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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