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Simpson Bay Villas

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    €631 Average
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    Travellers to Simpson Bay are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 40
    5 Bedrooms, 7 Bathrooms, Sleeps 10 | Quick View
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    1 / 25
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 13
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    €320
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    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 well-appointed... View all property information
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    Simpson Bay, Sint Maarten
    1 / 21
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    €205
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    • DVD Player
    • Parking
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    • Shared Garden
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    About this property
    This Exceptional, Exotic and Spacious 1,700 sq ft two bedroom duplex, very cozy and tastefully decorated with large private beach front terrace, is located in Simpson bay. Enjoy LUXURY and Total PRIVACY with spacious suites and a large living room that not even a suite at the best hotel in town can... View all property information
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    Simpson Bay, Sint Maarten
    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    €256
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    • Internet Access
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    • Pet-friendly
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    • x
    • x
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    • x
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    About this property
    Your Caribbean vacation begins on one of the prettiest unspoiled beaches on all of St. Maarten / St. Martin. Quiet, calm, lined with sea grapes and palms... and no one to interrupt the peace and tranquility. CocoBelle is situated on the southern end of Simpson Bay Beach, within the beachfront... View all property information
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    Simpson Bay, Sint Maarten
    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    €4,214
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    • DVD Player
    • Waterfront
    • Air Conditioning
    • Private Outdoor...
    • Hot Tub
    • Washer
    • Satellite TV
    • Wi-Fi
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    7th Night Free! Jan 5 - Dec 15, 2016Restrictions Apply!This property may accept holiday stays of less than 14 nights.Rates may vary depending on # of bedrooms rented. Please see rate table or call for details.St Tropez sits high up on the hill in Pelican Key in Dutch St Maarten and offers... View all property information
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    Simpson Bay, Sint Maarten
    1 / 23
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    €3,855
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    • Wi-Fi
    • Satellite TV
    • Private Outdoor...
    • Balcony
    • Terrace
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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.... View all property information
    Location Information
    Simpson Bay, Sint Maarten 97000
    1 / 21
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
    From
    €473
    / Night
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    • DVD Player
    • Internet Access
    • Grill
    • Parking
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Seachest is a 4 bedroom, 4 bathroom villa located in the Cote d Azur Marina, in the Dutch Lowlands of Sint Maarten. This spacious home sits right on the Simpson Bay Lagoon, and has a terrific view of the water and across to the French Lowlands. There is a boat dock available for use by the renter.... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 39
    4 of 5 stars (1) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    From
    €577
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    • Internet Access
    • Satellite TV
    • Private Outdoor...
    • Outdoor Dining Area
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
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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... View all property information
    Location Information
    Simpson Bay, Sint Maarten
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    From
    €489
    / Night
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    • Satellite TV
    • Air Conditioning
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    • Pet-friendly
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    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Villa LaLuna is one of the few homes on this wonderful island of Sint Maarten that is located on the beach. The inviting home has 4 of its 5 bedrooms that give you spectacular ocean views. The villa is also in a great location because you are within walking distance to great entertainment ,... View all property information
    Location Information
    Simpson Bay, Sint Maarten 97150
    1 / 16
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    From
    €628
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    • Washer
    • DVD Player
    • Grill
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful Alizes enjoys a stunning view over the water of Simpson Bay lagoon and the Caribbean in the distance. This 5 bedroom villa is located in Terres Basses within a community of only 6 villas featuring a private tennis court. Interior spaces include a spacious comfortable living room with lots... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €256
    / Night
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    • Washer
    • DVD Player
    • Satellite TV
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Villa Casella is a beautiful 3 bedroom and 2.5 bath condo overlooking the Simpson Bay Lagoon. It is conveniently located minutes away from shopping, beaches, casinos and restaurants. Here you get the feeling of a home away from home. This newly built unit, sleeps 6 people, comes fully furnished... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 23
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    €192
    / Night
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    • Washer
    • Satellite TV
    • DVD Player
    • Patio
    • Waterfront
    • Internet Access
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    'Tree Frog Villa' - Deluxe Oceanfront in Coral Shores Beautiful, pristine oceanfront villa, 25 feet from the sea. Two bedrooms, two baths, and a 42 foot covered porch facing the ocean and the sunsets. This is a gorgeous, guarded community of 27 private villas in a lush garden setting, in Pelican... View all property information
    Location Information
    Simpson Bay, Sint Maarten 00000
    1 / 25
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    From
    €1,793
    / Night
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    • Waterfront
    • Terrace
    • Private Outdoor...
    • Wi-Fi
    • Balcony
    • Grill
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 22
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
    From
    €3,138
    / Week
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    • Wi-Fi
    • Grill
    • Private Outdoor...
    • Air Conditioning
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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 in... View all property information
    Location Information
    Simpson Bay, Sint Maarten 97000
    1 / 61
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    €640
    / Night
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    • Grill
    • Balcony
    • Internet Access
    • Shared Garden
    • Terrace
    • Parking
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #50020221. (http://www.tico.ca/) Our Service Guarantee ensures you the best villa experience. (http://www.privatevillarentals.com/service-guarantee)... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 24
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
    From
    €11,656
    / Week
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    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor...
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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... View all property information
    Location Information
    Simpson Bay, Sint Maarten 97000
    1 / 23
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    From
    €576
    / Night
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    Amenities & Details
    • Grill
    • DVD Player
    • Internet Access
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to Villa dAcquario located in Point Pirouette, St. Maarten's most exclusive gated community adjacent to the Mullet Bay Golf Course. This waterfront Villa has four large bedrooms with five full bathrooms and can comfortably sleep eight people. An entertainment center and high-speed internet... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 23
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
    From
    €769
    / Night
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    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Internet Access
    • Outdoor Dining Area
    • Private Outdoor...
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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... View all property information
    Location Information
    Simpson Bay, Sint Maarten
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    1 / 10
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    €448
    / Night
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    • Patio
    • DVD Player
    • Satellite TV
    • Washer
    • Internet Access
    • Grill
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    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... View all property information
    Location Information
    Simpson Bay, Sint Maarten N A
    1 / 32
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    From
    €576
    / Night
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 4 or 5 bedrooms. The deck at Caribbean Blue is the perfect spot for enjoying the sun and sea, and has... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 22
    5 Bedrooms, 6 Bathrooms, Sleeps 2 | Quick View
    From
    €5,290
    / Week
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    • Private Outdoor...
    • Grill
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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... View all property information
    Location Information
    Simpson Bay, Sint Maarten 97700
    1 / 28
    7 Bedrooms, 9 Bathrooms, Sleeps 14 | Quick View
    From
    €9,414
    / Week
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    • Wi-Fi
    • Balcony
    • Private Outdoor...
    • DVD Player
    • Terrace
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    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 proclaimed as one of the Leading Estates of the World. This... View all property information
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    Simpson Bay, Sint Maarten 97000
    1 / 22
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    From
    €3,586
    / Week
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    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    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... View all property information
    Location Information
    Simpson Bay, Sint Maarten 97000
    1 / 19
    5 of 5 stars (3) Excellent
    7 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    From
    €807
    / Night
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    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Washer
    • Patio
    • Internet Access
    • Balcony
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    VILLA BELLA VITA - Where the amenities of Five Star Resort luxury meet with the casualness and privacy each guest desires. Named for the 'Beautiful Life' it represents, this property is renowned as one of the pre-eminent homes on the island of St. Maarten/St. Martin, and is a unique and... View all property information
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    Simpson Bay, Sint Maarten 99999
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    €282
    / Night
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Fabulous brand new apartment located at the Blue Residence in Cupecoy. With 2 bedrooms, the apartment occupies 2 floors with an impressive 180 degree view stretching from the ocean and Baie Longue beach over Porto Cupecoy and all the way across Simpson Bay lagoon. The first floor houses a spacious... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 10
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    From
    €6,724
    / Week
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    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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 the... View all property information
    Location Information
    Simpson Bay, Sint Maarten 97700
    1 / 46
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Grill
    • Washer
    • Private Outdoor...
    • Satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Rates may vary depending on # of bedrooms rented. Please see rate table or call for details.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 set with a delicious local cocktail in hand... View all property information
    Location Information
    Simpson Bay, Sint Maarten