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Simpson Bay Vacation Rentals

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    Travelers to Simpson Bay are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 153 Rentals in Simpson Bay
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    Blue Pelican Luxury Villas - Featured on HGTV!!!!!1 / 12
    (29)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Simpson Bay Beach Modern Luxury Ocean View 1 BR1 / 32
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW1 / 12
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Carisma on the beach1 / 22
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Housekeeping Included
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 20, 2017
    Thank you Paul and Carmen! Villa Carisma was the perfect choice for our family; such a beautiful beach front property.Our experience: We wanted a beach front property with...
    Reviewed June 27, 2017
    My wife and I stayed at Carisma to celebrate our 10 year wedding anniversary. The villa was absolutely amazing. Paul and Carmen could not have been better hosts and the villa is...
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    About this property
    An instant feeling of genuine coziness and warmth overcomes you upon entering Charisma. Tucked away she is, in a little maze of precious ocean front properties in the peaceful Pelican Key area. Overlooking the spectacular aquatic azure Caribbean Sea, this friendly two bedroom condo, truly will...
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    Simpson Bay, Sint Maarten 00000
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 BEDR townhouse overlooking OCEAN  ST- MAARTEN1 / 20
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 2, 2014
    I stayed at this villa with my family over the Christmas break. We had a fantastic time. My kids (10 and 7) enjoyed it very much. The place is very spacious and beatifully...
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    About this property
    Stylish , furnished 2 bedrooms, townhouse in quiet, residential area in Pelican, Rancho cielo Estates, Bathroom newly renovated with bath and rain shower, large master bedroom with furnished veranda with unobstructed ocean view. Walk-in closet. Very large open plan kitchen, courtyard with exotic...
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    Simpson Bay, Sint Maarten 000000
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Le Papillon Penthouse - REOPENED AFTER IRMA - roof top jacuzzi with great view1 / 24
    (6)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Ocean Views
    • Cable/satellite TV
    • Mountain Views
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 17, 2017
    We have been coming to St. Martin for the past 14 years and this time we brought the whole family with us. We rented both the penthouse and the 2 bedroom unit at the same time...
    Reviewed April 25, 2017
    Just returned home from a fantastic 10 night stay at the beautiful Le Papillion penthouse. Everything was perfect! We arrived at the villa and we were greeted by Simona, our...
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    About this property
    Welcome in Le Papillon Penthouse, the best experience on Simpson Bay beach. - Gated, private & secure community - 3 floor penthouse - 4560 sq. feet unit - Cleaning service every second day - Roof terrace with long chairs, dining area, summer kitchen and 360 degrees view - Private jacuzzi on the...
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    Simpson Bay, Sint Maarten 00000
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    2BR-Oceanfront-Royal Palm1 / 20
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Ocean Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 15, 2017
    This was our first time staying at the Royal Palm. We usually stay over in Maho, but due to a scheduling mix up, we ended up at the Royal Palm. Both my mom and I have been to St...
    Reviewed February 14, 2017
    Friendly staff will help any way they can, from front desk to housekeeping. Clean rooms with full kitchen setup. Free WIFI in rooms although not very dependable.Great view from...
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    About this property
    Royal Palm Beach Resort in Simpson Bay is one of the most liked resorts on the island. All units face the ocean and are 2 bedrooms with a king size bed in each, and a living room with a queen size sleeper sofa. Units have full kitchens, dining room table, seating for 6, and a balcony with a table...
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    Simpson Bay, Sint Maarten 00SXM
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Le Papillon - REOPENED AFTER IRMA - Modern Beachfront Unit with great view1 / 24
    (4)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 25, 2017
    Pros: -View from apartment balcony is spectacular. The pictures are really not photoshopped. - Apartment is very modern, very clean and very well equipped- Apartment is...
    Reviewed May 17, 2017
    We have been coming to St. Martin for the past 14 years and this time we brought the whole family with us. We rented both the penthouse and the 2 bedroom unit at the same time...
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    About this property
    Welcome in Le Papillon, the best experience on Simpson Bay beach. -Gated, private and secure community -2150 sq. feet unit -Cleaning service every third day -Private parking inside the property -40“ smart TV in each bedroom with Netflix and satellite -48“ high definition smart TV in the living...
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    Simpson Bay, Sint Maarten 00000
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Studio in Pelican Key Paradise1 / 11
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 18, 2014
    We stayed in Jackies Appartement for 10 days. The Appartement is new renovated and has a nice littel Balkony surrounded by palm trees. It has a brand new shower with different...
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    About this property
    Newly renovated studio features a kitchenette with full fridge, 4 burner glass stove top, microwave, toaster oven, and coffee maker. King size, very comfy bed, flat screen cable tv, and sofa, bathroom with multi jets including rain shower head, and a balcony with seating for 4 overlooking the...
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    Simpson Bay, Sint Maarten 00014
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Anchorage Apartment1 / 18
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Ocean Views
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 30, 2016
    Loved Martine's apartment! It is right across the road from the beach and close to all the sights and ammenities in Simpson Bay. Martine was excellent to deal with and she made...
    Reviewed April 12, 2015
    This is a return trip to this apartment, that is how much we have liked it in the past. This trip again, we had a wonderful time. The apartment is is big enough for 4, with all...
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    About this property
    Beautiful beach side apartment with spectacular ocean view in Simpson Bay. Come stay and enjoy the beautiful sunsets and relax on the beach! Surrounded by top rated restaurants, bars, supermarkets, casino's and nightlife. Private car parking. Child friendly. Fully equipped apartment, come over and...
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    Location Information
    Simpson Bay, Sint Maarten 11111
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Cool Bay Villa St Maarten1 / 21
    (16)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 10, 2016
    We rented this adorable villa with our two teenage kids for a Caribbean Christmas Vacation. The beginning of our vacation didn't start off so well. The owners were out of town...
    Reviewed September 17, 2014
    Go!! For tomorrow is later. Near there supermarket, and drugs. The Maho Beach is near in car too. Near there Dominican food, no is so expensive.
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    About this property
    Rigth next to St Maarten' s Lagoon - A lovely setting, surrounded by trees and plants. Just a short 2 miles hop to the beach, this traditional Caribbean (65m2) villa is ideal for a family. Fully air-conditionned,it has a terrace and a balcony with garden furniture, including hammock, parasol and...
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    Location Information
    Simpson Bay, Sint Maarten 97150
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Vacation Villa at Simpson's bay and Marina1 / 26
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Ocean Views
    • Housekeeping Included
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 23, 2016
    I have stayed here 3 times and I am going back in Oct 2016 for TWO weeks! I am so thrilled w/this resort and rooms to stay in. The food is awesome and reasonably priced. The...
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    About this property
    Your home away from home on the Caribbean island of St. Maarten, is ideally positioned on the beach, midway between the island's most popular night spots and shopping. Fine Restaurants abound to tempt your pallet and an Activity Center makes it convenient for excursions to dive/snorkel spots along...
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    Simpson Bay, Sint Maarten 00000
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    El Zafiro: Aquamarine Suite- Breathtaking views!1 / 22
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Housekeeping Included
    • Terrace
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Secure Parking
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 7, 2017
    El Zafiro is simply an amazing place to stay. We rented the aquamarine suite. The room was very clean and nice and the beach is directly outside of the room. Maho Bay is a...
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    About this property
    El Zafiro will lay world class luxury at your feet, your choice of a suite guarantees you an unforgettable experience the moment you walk through the gates. The lavish interior and beautiful sandy beach will transport you to another world and melt away your cares and stress. The Aquamarine suite...
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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Patio
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect location between Simpson Bay & Philipsburg,in the new gated community of'Indigo Bay Beach'. This brand new exquisite residence, very well modern decorated & equipped. Beautiful living area, lots of glass doors that open to a private pool, wrapped by a huge deck offering incredible panoramic...
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    Simpson Bay, Sint Maarten NA
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Pelican Key 1Bedroom For Rent1 / 9
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Internet Access
    • Cable/satellite TV
    • Balcony
    • Terrace
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1 bedroom/1bath unit is located in Pelican Key/Simpson Bay' next to LaVista Resort. Within walking distance to many restaurants, bars, grocery store and casino. The unit has a full kitchen with all the comforts of home, a futon sleeper sofa and cot downstairs for 2 and a bedroom with a king...
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    Location Information
    Simpson Bay, Sint Maarten 00090
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Balcony
    • Housekeeping Included
    • DVD Player
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful brand new residence was built atop the cliffs in Beacon Hill overlooking Simpson Bay and only a few steps to the beach ; The condo has everything from contemporary design to high end bedding and a spacious gourmet kitchen one would want for a luxury tropical vacation. A short 2...
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    Simpson Bay, Sint Maarten 1744
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Survived Irma!!  Beachfront gated Condo directly on Simpson Bay1 / 16
    (4)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Waterfront
    • Grill
    • Air Conditioning
    • Washer
    • Ocean Views
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 14, 2017
    We spent a week at Kelly and EJs beautiful condo at The Palms.This condo is spacious, bright and inviting. There is everything from a full kitchen, beach towels, information...
    Reviewed January 7, 2015
    We recently rented a 1 bedroom at Simpson Bay Resort. Although we were in the older building that was in need of some updating we were very pleased with the size of our room...
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    About this property
    Survived Irma!! Beautifully decorated 2 bedroom, 2.5 bath villa located directly on Simpson Bay Beach at Palm Beach Condos on the Dutch Side of St. Maarten, a new intimate and well designed gated community of only twenty-four units, all facing both the pool and the beach beyond. The layout was...
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    Location Information
    Simpson Bay, Sint Maarten 00000
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely ocean edge condominium is located in a nice and peaceful neighborhood of Beacon Hill. Within 10 min walking distance from all attractions of the famous MAHO bay: beaches, restaurants, bars, casinos, nightclubs, grocery stores and druggist. Enjoy the sunrise on the front porch, sunset...
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    Simpson Bay, Sint Maarten 97150
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    BEACHFRONTBLISS1 / 15
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Ocean Views
    • Terrace
    • Patio
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ◾first floor direct access to the pool and beachfront ◾amazing 3 ½ mile crescent of powdery white sand beach with gentle waves ◾private pool front lanai accessible from the master bedroom and living area ◾large, fully functional kitchen, all granite ,new, top grade appliances and all kitchen...
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    Simpson Bay, Sint Maarten NONE
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Housekeeping Included
    • Washer
    • DVD Player
    • Grill
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This third floor end unit ON THE BEACH offers plenty of privacy along with magnificent ocean views. The intimate 12-unit complex has gated private parking as well as its own pool just steps from the sand. It sits beachfront just a short walk from restaurants and shopping of Simpson Bay. Karakter...
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    Simpson Bay, Sint Maarten SX
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Balcony
    • Washer
    • Patio
    • Terrace
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely ocean edge condominium is located in a nice and peaceful neighborhood of Beacon Hill. Within 10 min walking distance from all attractions of the famous MAHO bay: beaches, restaurants, bars, casinos, nightclubs, grocery stores and druggist. Enjoy the sunrise on the front porch, sunset...
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    Simpson Bay, Sint Maarten 97150
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Caribbean Sun1 / 33
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 31, 2016
    The entire property is very well maintained (pool and grounds were great, nice beach), and our condo had everything we needed. Terrific grocery shopping literally five minutes...
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    About this property
    This is a great property if you if you like low key with a fantastic view. Being in the middle of Simpson Bay you can walk a mile in either direction. The property has a great pool and the beach in front is never crowded. The owner has outfitted the unit with most everything to make your stay very...
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    Simpson Bay, Sint Maarten SAINT MARTIN
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Ocean Views
    • Balcony
    • Grill
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful 1 bedroom Condo is set high up on Pelican key. It is Quiet secluded and only 5 minutes walk from the beach. Its very modern, clean and luxurious. A perfect quiet secluded hideaway! All amenities are close by, shops, casino and the beach.... not too far from all the great restaurants...
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    Location Information
    Simpson Bay, Sint Maarten SXM
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This one bedroom condo unit is located in beacon hill on the ocean with views from both sides of the unit. You are within shorts distance and even walking distance should I say to great beaches such as the simpson bay beach or mullet bay beach, to restaurants, casinos, bars and any other...
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    Location Information
    Simpson Bay, Sint Maarten 97150
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This one bedroom townhouse is in one of the most desired areas on St Maarten. Pelican Key has bars, restaurants, beaches, and a casino, all within a 10 minute walk. The unit sets on the 2nd and 3rd floor of a small condo complex, with a shared swimming poo. The unit has some nice views from the...
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    Location Information
    Simpson Bay, Sint Maarten 000NA
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Waterfront
    • Wi-Fi
    • Housekeeping Included
    • Air Conditioning
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This brand new 2 bedrooms, 2 bath villa is located in Beacon Hill on the Cliffside overlooking the stunning Simpson Bay Beach. This villa has a very private pool area with mazing views on the ocean. The Front part of the property is great at night to enjoy the colorful sunsets.  The property is...
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    Location Information
    Simpson Bay, Sint Maarten 9999 XX
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 5 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Waterfront
    • Housekeeping Included
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coco's Beach #5 is a beautiful location for your vacation or stay in St. Maarten! Located right on the beach in Simpson Bay, you will wake every morning to the sights and sounds of the ocean. Living room and master bedroom have full ocean access with a large outdoor private deck. Enjoy the clean...
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    Location Information
    Simpson Bay, Sint Maarten 0000
    Condo/Apartment - 2 Bedrooms, 5 Bathrooms, Sleeps 6
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    WITENBLAUW... Irma Survivor, 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
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 14, 2015
    Well worth the money!! Not only was the estate exactly as pictured, the housekeeping and grounds staff was terrific as well. We will definitely be returning.....
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    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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    Location Information
    Simpson Bay, Sint Maarten
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Hot Tub
    • Wi-Fi
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    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Simpson Bay Beach Condo #2 is a beautiful ground floor, well equipped, fully air-conditioned condo located directly on Simpson Bay Beach. Walk off your patio and onto a wonderful soft sandy beach! Enjoy quiet mornings with the birds singing or take an early morning stroll or dip on beautiful, two...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    RENDEZVOUS... IRMA Survivor!! A fabulous 2 BR contemporary 2 BR condo unit  on1 / 14
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 14, 2017
    An outstandingly property with an infinity pool overlooking Simpson Bay beach. The entire complex of 12 units is meticously maintained and has its own water tank and generator...
    Reviewed December 20, 2016
    Very well appointed, tastefully furnished, fully equipped condo right on the beach at Simpson Bay. Beautiful terrace to eat outside or lounge with stunning view and the...
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    7th Night Free! Aug 10 - Dec 15, 2017 Maid Service offered 2x p/week when booking the 7th Night Free Promo RatesPlease inquire about lower rates offered for less than full occupancy.Rendezvous, from the moment you set foot inside the luxurious St. Maarten vacation rental, gated courtyard of Las...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Washer
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Sauna
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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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
    Rental Home - 2 Bedrooms, Sleeps 4
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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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    • Patio
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    Suitability
    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
    Rental Home - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    Paradise Found at Las Arenas - Beachfront Luxury!1 / 18
    (10)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Ocean Views
    • Housekeeping Included
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 4, 2017
    This luxury condo is better than described. Easy to find, safe, beautiful and peaceful. The beds were extremely comfortable. The view is amazing. We are early risers and...
    Reviewed November 30, 2015
    What a great find. We stayed at this beautiful property the 2nd week of November and couldn't of asked for a nicer place that was centrally located. The condo was immaculate...
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    HURRICANE IRMA UPDATE (September 30, 2017) Miraculously, Paradise Found was virtually unscathed but the building and grounds sustained some damage so I'm unable to take reservations at this time. I'm confident and optimistic that Las Arenas will return to it's elegant beauty by February 2018 and...
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    Simpson Bay, Sint Maarten 00000
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Villa Vita on the beach St Maarten,Caribbean1 / 33
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Internet Access
    • Cable/satellite TV
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 9, 2017
    We had very high expectations for our trip since we had visited St. Maarten before and we were not disappointed. We had read it was in a new development with some construction...
    Reviewed January 5, 2017
    We brought our family (4 children, 2 adults) to St Maarten and elected to rent a Villa instead of staying at the Royal Palm (we have stayed here many times). We have been to...
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    About this property
    A beautiful new house in a new development, within a quiet gated community, with security onsite. Yet it is just a few minutes to great restaurants, duty free shopping, casinos, spas and grocery stores. And only 10 minutes from Princess Julianna Airport. Our 3 bedroom house comfortably sleeps 6...
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    Simpson Bay, Sint Maarten NA
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
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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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Parking
    • Washer
    • Cable/satellite TV
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • 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.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...
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    Simpson Bay, Sint Maarten
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Coco Beach Duplex1 / 21
    (3)Average
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 11, 2015
    This was our second stay at Cocos Beach Duplex on Simpson Bay. You simply cannot beat the location and convenience of this comfortable townhouse/duplex - we love it. We...
    Reviewed September 6, 2013
    Great private villa on beautiful screen saver white sand beach 20 feet to Caribbean sea quiet .private patio luxury in & out villa with unbelievable view's great for familys...
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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...
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    Simpson Bay, Sint Maarten 11111
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Housekeeping Included
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    Pet friendly
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    Smoking allowed
    About this property
    Located a mile away from the airport, El Zafiro flawlessly blends St Maarten style with fabled glamour. As with every guest in an El Zafiro suite, you are our VIP guest and the turquoise suite will remind you of this every day. With adornments of green and blue, delicate fabric and contemporary...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Wi-Fi
    • Housekeeping Included
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique, romantic, comfortable STUDIO in beautiful residential area completely equipped with linens, AC, TV, cable, Wi-Fi, kitchenette, pool, parking right in front. Quiet location with easy access to restaurants, entertainment, beach, casino. water sports, <BR>Airport is within 10...
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    Simpson Bay, Sint Maarten 0000
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
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    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wow! Sur Mer is one of those rare affordable 3 bedrooms, 3 bath condos on a gorgeous white sandy beach! This spacious, well-furnished beachfront condo is located smack dab on Simpson Bay Beach in the lovely gated community of Coco's Beach Club! Walk up a flight of stairs to heaven on the beach!...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Air Conditioning
    • DVD Player
    • Grill
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    • Private Outdoor Pool (Unheated)
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7th Night Free! Apr 15 - Dec 15, 2017Restrictions Apply!Pleas inquire about lower rates offered or less than full occupancy.La-Di-Da is a gorgeous 6 bedroom, 6 bath St. Maarten vacation villa that sits high atop a mountain at the mouth of Pelican Key. This mountain top setting provides wonderful...
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    Simpson Bay, Sint Maarten
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Terrace
    • Balcony
    • Patio
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This one bedroom condo unit is located in beacon hill on the ocean with views from both sides of the unit with view that only one could dream about. You are within shorts distance and even walking distance should I say to great beaches such as the simpson bay beach or mullet bay beach. The condo...
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    Simpson Bay, Sint Maarten 97150
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    The Blue Frenchie: Gorgeous 2-story townhouse in Pelican Key, St. Maarten1 / 19
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • Mountain Views
    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 11, 2017
    Loved being able to meet with Astrid, who was very welcoming and answered all of our questions and gave us great suggestions as to where to go and what to see. But, we mostly...
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    About this property
    Elegant townhouse in highly desired Pelican Key address, conveniently located central to everything in St. Maarten and only a 12 minute drive from SXM airport. Fully remodeled 2-story townhouse in privately gated community with ocean view and within walking distance of the most popular restaurants...
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    Simpson Bay, Sint Maarten PELICAN KEY ST MAARTEN
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    COCO BEACH CLUB 6...walk right out onto the beach at Simpson Bay1 / 20
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 27, 2017
    We've been vacationing in St. Maarten for over 25 years and have had the pleasure of staying in many beautiful villas and hotels. We were back for the 2nd time to Coco Beach...
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    A Wonderful Place!!! Coco Beach Club #6 beach front St. Maarten vacation rental, Dutch St Maarten , Simpson Bay Beach, near Maho night life.Wake up in the morning and walk right out onto the beach at Simpson Bay when you stay at this new 2 bedroom 2 bath St Maarten rental condo. Coco Beach #6 has...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Aqualina 102 - Ideal for Couples and Families, Beautiful Pool and Beach1 / 15
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Reviewed July 7, 2016
    Just stayed a Aqualina for 6 amazing night that never dissappointed us! The views are incredible-steps to the beautiful turquoise sea. Condo was gated with security and nicely...
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    About this property
    Crystal clear turquoise sea flecked with dazzling tropical sun, powdery white sands stretching along one of St. Maarten’s longest beaches; Lush exotic foliage surrounding an elegant building of architectural beauty. All of this belongs to Aqualina, St. Maarten’s newest luxury beach front...
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    Simpson Bay, Sint Maarten 97700
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Washer
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'At Seaside' is our dream...make it yours too! Serene Caribbean views can be enjoyed from the terrace. She is one of 20 units in a gated community surrounding a pool with views of the Caribbean. The grounds are lush and well tended. There is a king-sized bed and master bath off the bedroom. There...
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    Simpson Bay, Sint Maarten 000
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Ocean Views
    • Cable/satellite TV
    • Housekeeping Included
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom, 2.5 Bath On The Water. Luxury At Its Best!!! This contemporary 5 star resort condo is now available for your enjoyment. Located on the ground floor this unit has an amazing spacious deck just steps from the waters' edge. Feel the breeze as you sip your coffee in the morning or enjoy a...
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    Location Information
    Simpson Bay, Sint Maarten 33023
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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