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Simpson Bay Villas

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    98 Matching Rentals in Simpson BayView all 185 rentals
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    Travellers to Simpson Bay are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    7 Bedrooms, Sleeps 14Quick View
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    3 Bedrooms, Sleeps 7Quick View
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    • Private Outdoor Pool (Unheated)
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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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    • Terrace
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    Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #********. Our Service Guarantee ensures you the best villa experience. This 5 Bedroom Villa can be rented as a 2 or 3 Bedroom Villa at special rates! In...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, Sleeps 10Quick View
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    • Grill
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    Pet friendly
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    About this property
    Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #********. Our Service Guarantee ensures you the best villa experience. This 5 Bedroom Villa can be rented as a 2 or 3 Bedroom Villa at special rates! In...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    St Tropez sits high up on the hill in Pelican Key in Dutch St Maarten and offers outstanding views of the Caribbean Sea and glorious sunsets.  St Tropez is comfortably furnished and well decorated and the spacious living room opens up completely to the pool terrace and the amazing views beyond. ...
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    Simpson Bay, Sint Maarten 97000
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, Sleeps 12Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    Spacious 6 bedroom, 6 bath villa on top of the World with spectacular views of the ocean, Simpson Bay, Lowlands and Saba with additional 2 bedrooms, 2 bath apartment in the lower level of the house! Huge private pool with infinity edge. House has seen a 2 year renovation with upgrade of the...
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    Simpson Bay, Sint Maarten 97000
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, Sleeps 6Quick View
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    • Terrace
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    Pet friendly
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    Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #********. Our Service Guarantee ensures you the best villa experience. Speranza, this three bedroom contemporary villa is located on a hillside facing...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    This beautiful beachfront 5 bedroom, is located in the quiet area of Beacon Hill overlooking Burgaux Bay. Villa Hardman offers great views in the morning of the grand cruise ships and amazing colors during the sunsets. The villa is within walking distance to Maho which is one of the most popular...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, Sleeps 4Quick View
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    • Air Conditioning
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    Pet friendly
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    Ava is 2 bedrooms/2 bathrooms apartment in the luxurious Porto Cupecoy. The spacious open plan living area is fully air conditioned, with a well equipped American style kitchen. This space opens to the sheltered terrace overlooking the moored yachts and the marina. Porto Cupecoy is a secured...
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    Simpson Bay, Sint Maarten 00000
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Review
    3 Bedrooms, Sleeps 6Quick View
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    Villa Smart is nestled beachfront at Pelican Key and offers a totally tropical, affordable family St. Maarten vacation rental with direct beach access and glorious ocean views, does not have a swimming pool....The terrace, full of lush vegetation, is truly a special place of relaxation and...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Pet friendly
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    About this property
    Villa Riviera is a St. Maarten vacation villa rental, located high on the hillside at Pelican Key, with an unobstructed view of the Caribbean Sea from every room.Each room opens to the patio which runs the entire length of the villa. Swim in a private pool overlooking this scenic Caribbean vista....
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Review
    5 Bedrooms, Sleeps 10Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Caribbean Blue is a beachfront home in Pelican Key. With five bedrooms and bathrooms, it is the perfect house for a family vacation. Caribbean Blue may be rented with use of either 3, 4 or 5 bedrooms. The deck at Caribbean Blue is the perfect spot for enjoying the sun and sea, and has wonderful...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    • Grill
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    Pet friendly
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    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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    2 Bedrooms, Sleeps 4Quick View
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    Aqualina 102 St Maarten. Families or groups of four often find it difficult to locate luxury accommodations with the same long lists of amenities that larger villa properties offer. However, Villa Aqualina Beach Club Unit 102 has been created with such groups in mind. With two bedrooms and 2.5...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Beautiful Villa Provence…from its majestic setting up on the Pelican Key to its breathtaking sunsets every evening with a delicious local cocktail in hand with your private pool on the wraparound veranda., in the sun or in the shade. What a lovely way to spend the days on the friendly island…the...
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    Simpson Bay, Sint Maarten 97000
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Sapphire, the perfect vacation home, is a charming Caribbean styled house nestled in lush tropical gardens. Sitting high on a hillside in the exclusive Pelican Key area, the house offers wonderful views of the Caribbean Sea and St. Maarten’s spectacular sunsets. Each of the...
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    Simpson Bay, Sint Maarten 97700
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    La Casita Villa is the perfect destination if you are looking for a romantic getaway or an unforgettable vacation with family or friends. This vacation home is ideal for 2 to 6 people. La Casita is an exceptional 3 bedroom, 3 bathroom private home located on the oceanfront. This villa is...
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    Simpson Bay, Sint Maarten DWI
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    St Tropez sits high up on the hill in Pelican Key in Dutch St Maarten and offers outstanding views of the Caribbean Sea and glorious sunsets.  St Tropez is comfortably furnished and well decorated and the spacious living room opens up completely to the pool terrace and the amazing views beyond....
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    Simpson Bay, Sint Maarten 97000
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Reviews
    5 Bedrooms, Sleeps 10Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Caribbean Blue is a beachfront villa in Pelican Key. With five bedrooms and five and a half bathrooms, it is a perfect house for a family vacation! The deck at Caribbean Blue is the perfect spot for enjoying the sun and sea, and has wonderful views of the island of Saba, and of the sunset. Pelican...
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    Simpson Bay, Sint Maarten 78866
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    • Waterfront
    • Terrace
    • Private Outdoor Pool (Unheated)
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 four or five bedrooms. Maid service daily, except weekend and Holidays. The deck is the perfect...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Feel like you are transported to the Mediterranean at Villa Riviera. Enjoy this splendid villa, located high on the hillside at Pelican Key, with an unobstructed view of the Caribbean Sea from every room.  Each room opens to the enormous patio which runs the entire length of the villa. Swim...
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    Simpson Bay, Sint Maarten 97000
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Rates may vary depending on # of bedrooms rented. Please see rate table or call for details.Daffodil is a multi million dollar beautiful 5 bedroom 5 bath oceanfront St Maarten vacation rental villa that features colorful tropical furnishings and decorations with 5 full king bedrooms and 5 luxurious...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Faja Lobie has become a very popular rental home over the last two years. This beautiful, newly renovated three bedroom, three bath villa sits directly on Bourgeaux Bay beach in the residential area of Beacon Hill on the Dutch side. This home offers a wonderful combination of indoor and outdoor...
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    Simpson Bay, Sint Maarten 78866
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, Sleeps 12Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful beachfront 5 bedroom, is located in the quiet area of Beacon Hill overlooking Burgaux Bay.  Sunset offers great views in the morning of the grand cruise ships and amazing colors during the sunsets.The villa is within walking distance to Maho wihch is one of the most popular tourist...
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    Simpson Bay, Sint Maarten 97700
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    9 Reviews
    2 Bedrooms, Sleeps 5Quick View
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    • Patio
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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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    6 Bedrooms, Sleeps 12Quick View
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    • Patio
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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 97000
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 wonderful privacy at the villa. From the living areas, decks and pool area you are...
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    Simpson Bay, Sint Maarten 78866
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, Sleeps 12Quick View
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    About this property
    Provence is a beautiful 6 bedroom, 4.5 bathroom villa with gorgeous views located in Pelican Key. This villa features a well-equipped kitchen, dining area, air-conditioned bedrooms - 5 bedrooms have king size beds and the 6th has 2 twin beds, 3 ensuite bathrooms, 1.5 shared bathrooms, a pool and...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, Sleeps 10Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Summer Hill is a free standing private villa perched on top of one of the hills of Pelican Key, Dutch St. Maarten.  The villa boasts 200 degree views of the turquoise waters of the Caribbean Sea and on a very clear day you can see the neighboring islands of Saba, Statia, St. Kitts and Nevis....
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    Simpson Bay, Sint Maarten 97000
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, Sleeps 12Quick View
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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 0000 AA
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    About this property
    7th Night Free! Apr 15 - Dec 15, 2017Restrictions Apply!St Tropez sits high up on the hill in Pelican Key in Dutch St Maarten and offers outstanding views of the Caribbean Sea and glorious sunsets. This St. Maarten vacation villa for Heineken Regatta participants or fans. St Tropez is comfortably...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, Sleeps 2Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 97150
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 2
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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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    5 Bedrooms, Sleeps 10Quick View
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    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, Sleeps 6Quick View
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    Sapphire villa, the perfect St. Maarten vacation rental, is a charming Caribbean styled house nestled in lush tropical gardens. Sitting high on a hillside in the exclusive Pelican Key area. The villa offers wonderful views of the Caribbean Sea and Dutch St. Maarten's spectacular sunsets. Each of...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    round floor, 1 bedroom, 2 bath apartment professionally and tastefully decorated throughout. Ceiling windows, bathrooms with deep-soak Jacuzzi tubs and rain shower heads, both bathrooms have granite counter- tops with European style vanities, expansive living room with views of Maho Bay and the...
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    Simpson Bay, Sint Maarten 97000
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    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 open...
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    Simpson Bay, Sint Maarten 78866
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    6 Bedrooms, Sleeps 12Quick View
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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, Sleeps 12
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    Pet friendly
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    About this property
    “The Reef “ is a beautiful 5 bedroom contemporary villa, superbly positioned on the Simpson Bay Lagoon on the Dutch side of the island of St. Martin/St. Maarten. The villa has its own private boat dock, an amazing lounging terrace with very private exterior living areas and a beautiful waterfront,...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    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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    3 Bedrooms, Sleeps 6Quick View
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    Pet friendly
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    St. Tropez sits high up on the hill in Pelican Key in Dutch St. Maarten and offers outstanding views of the Caribbean Sea and glorious sunsets. St Tropez is comfortably furnished and well decorated and the spacious living room opens up completely to the pool terrace and the amazing views beyond....
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    Simpson Bay, Sint Maarten 0000 AA
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Pet friendly
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    Smoking allowed
    About this property
    Located over the hill on the sea at Pelican Key, Daffodil is a luxurious five bedroom, five bath villa, whose unique glistening cerulean blue tile roof promises a memorable vacation experience. Its Dutch flavor is showcased by colorful furnishings from international designers, and represents the...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Pet friendly
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    Smoking allowed
    About this property
    Summer Hill is a free standing private villa perched on top of one of the hills of Pelican Key, Dutch St. Maarten. The villa boasts 200 degree views of the turquoise waters of the Caribbean Sea and on a very clear day you can see the neighboring islands of Saba, Statia, St. Kitts and Nevis. This...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, Sleeps 8Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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 flavor is showcased by colorful furnishings from international designers, and represents the...
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    Simpson Bay, Sint Maarten 78866
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 8
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    6 Bedrooms, Sleeps 12Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled on the beautiful beach of Burgeaux Bay in the area of Beacon Hill in Dutch St. Maarten, Villa Sunshine is a wonderfully spacious 6 bedroom, 6 bathroom home offering beautiful views over the ocean. The villa is constructed on one level providing easy access and movement and has a vibrant...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Travelers Choice Award for 2015 & 2016 and Rated Best Vacation rental in St. Maarten for 2012 - 2014, Blue Pelican Villas is located on the Dutch side of St. Maarten in the exclusive area of Pelican Key. Blue Pelican is a spacious 1 bedroom villa set on an upscale property with a wonderful interior...
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    Simpson Bay, Sint Maarten PELICAN KEY
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Spacious studio apartment with breathtaking views for rent. Located on the island of St. Maarten in the heart of the Caribbean, this fully equipped studio, located a few minutes from all amenities is your perfect tropical getaway.Enjoy our beautiful island at its best and relax at the end of a full...
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    Simpson Bay, Sint Maarten 99999
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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