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Simpson Bay Villas

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    Travellers to Simpson Bay are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    74 Matching Rentals in Simpson BayView all 155 rentals
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Coral Breeze - STM1 / 16
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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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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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    “La Vista Grande” ( 4 bedroom villa) is a paradise found on an island paradise. Sitting atop the cliffs of the Beacon Hill peninsula La Vista Grande lives out it’s name ” The Grand View”. Majestic mountains, white sand beaches and the sparkling turquoise sea are only the beginning of your...
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    Simpson Bay, Sint Maarten 97700
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    You can snorkel or swim straight from your breakfast table or bedroom. You can sit in the shade of the sea grape trees or relax by the pool in a hammock while watching the spectacular sunsets. The ever present trade winds provide cool breezes while viewing the neighboring islands from the large...
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    Simpson Bay, Sint Maarten 97700
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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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 97700
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    About this property
    A modern 3-bedroom, 2-bathroom beauty overlooking beach/vast views of the ocean in new Indigo Bay development. Sunset viewing on the deck, dipping your feet in the private pool or walking down to the beach, this house has it all! Centrally located. All the bedrooms have a view of Kokomo Beach and...
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    Simpson Bay, Sint Maarten 97700
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Villa is located in Pelican Cove, a private gated community in Pelican Key located in the Simpson Bay area. This private villa is located directly on the water, has two bedrooms and an open living concept. Additionally, it has a large patio with a completely private pool. You can enjoy the...
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    Simpson Bay, Sint Maarten COLE BAY
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Ocean Views
    • Terrace
    • Balcony
    • Housekeeping Included
    • Patio
    • DVD Player
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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, 6 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Air Conditioning
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    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 97700
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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)
    • Housekeeping Included
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    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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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Waterfront
    • Internet Access
    • Cable/satellite TV
    • DVD Player
    • Parking
    Suitability
    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 00000
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Horizon says it all in the name... Come enjoy the views that will absolutely mesmerize you!  This immaculate contemporary villa will be your sanctuary away from it all. Located hillside in Almond Grove Estates, a 24-hour secured gated community in Dutch St. Maarten. You'll be just 2 minutes...
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    Simpson Bay, Sint Maarten 97700
    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
    • Cable/satellite TV
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    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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    Location Information
    Simpson Bay, Sint Maarten 000
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Grill
    • Balcony
    • Internet Access
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Tevaa, an amazing location for this villa in Sint Maarten (Pointe Pirouette) near Maho and Mullet Bay. Villa Tevaa 3 bedrooms, feet in the water, has everything to make you spend an unforgettable stay in Sint Maarten. The layout and vegetation will preserve your privacy. The villa can host 6...
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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 10 Quick View
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    • Wi-Fi
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    • Patio
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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 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 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Hot Tub
    • Washer
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7th Night Free! Apr 15 - Dec 15, 2017Sol Y Mar, a charming second-level private penthouse villa, nestled between a vibrant collection of favorite eateries, bars, branch style bakeries and the lapping turquoise waters of Simpson Bay – the heartbeat of the Dutch side. As the saying goes, “location,...
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    Simpson Bay, Sint Maarten 99999
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Internet Access
    • Washer
    • Parking
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 equipped with flat screen TV, a dining area with seating for 10 and a fully equipped kitchen....
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    Location Information
    Simpson Bay, Sint Maarten 00000
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Washer
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The villa offers amazing colors in the morning and unique sunsets and is located within walking distance to casinos and nightlife and some great restaurants including Bamboo Bernies and Le Moulin Fou. The villa features 2 levels with 4 of the bedrooms situated on the ground floor and a master suite...
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    Location Information
    Simpson Bay, Sint Maarten 00000
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Cable/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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