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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 171 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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    2BR-Oceanfront-Royal Palm1 / 10
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Le Papillon - Modern Beachfront Unit, stunning view, great amenities1 / 24
    (4)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 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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    • Grill
    • Satellite TV
    • DVD Player
    • Ocean Views
    • Patio
    • Wi-Fi
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 12, 2017
    Lovely hostess - Eve Marie!!! We were greeted with two cold Heineken and a bottle of wine in the refrigerator. Thank you! Our rental was a studio. My husband and I had a short 5...
    Reviewed August 7, 2017
    My husband and I spent a wonderful 5 days vacation at Francois and Eve Marie's studio apartment in Pelican Key, St Maarten. Thank you Eve for the ice cold Heineken beers and...
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    About this property
    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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    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
    • 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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    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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
    • 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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    Le Papillon Penthouse - Stunning, modern beachfront unit with private roof top1 / 24
    (6)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Ocean Views
    • 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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    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
    • 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.<BR>Come stay and enjoy the beautiful sunsets and relax on the beach!<BR>Surrounded by top rated restaurants, bars, supermarkets, casino's and nightlife.<BR>Private car parking.<BR>Child friendly.<BR>Fully equipped apartment,...
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    Simpson Bay, Sint Maarten 11111
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Grill
    • Ocean Views
    • DVD Player
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 8, 2014
    Apartment is private, has all new appliances, including washer and dryer and dish washer. Hot water is freely available (not always true on every island we've stayed at...
    Reviewed January 17, 2014
    This private residence is located in a quiet residential area with a wonderful host. It has everything you need and is centrally located close to a large grocery store and...
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    About this property
    Modern 1 bedroom apartment newly built. Marble floors through out. All stainless steel appliances in kitchen and granite counter top. Hi speed WiFi internet. Dish Network Satellite TV in living room and bedroom. Air conditioning in all areas. Very private due it being a single detached apartment...
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    Simpson Bay, Sint Maarten NA
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Villa Balaclava - Luxury villa " MAGNIFIQUE & Full Privacy "1 / 96
    (2)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Ocean Views
    • Waterfront
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 22, 2016
    This beautiful Villa is close to all of the places that we like to go, You are close to the bars and restauraunts in Simpson's Bay, The airport and Maho are a short drive. The...
    Reviewed January 17, 2016
    What a great place Michael was amazing We had a small problem we called Michael and he was shortly and had it fixed and followed to make sure everything was working well
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    About this property
    A modern tropical retreat in an enclave of privacy offering breathtaking views over the Caribbean sea. Located a few minutes drive away from: - Hollywood Casino - Buccaneer Beach Bar BBQ - Supermarket - French Bakery serving breakfast all day and lunch, Take a stroll on the beach, shopping...
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    Location Information
    Simpson Bay, Sint Maarten 00000
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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
    • 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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    El Zafiro: Ruby Suite - Unforgettable Getaway!1 / 23
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Housekeeping Included
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As with every guest in an El Zafiro suite, you are our VIP, and the Ruby suite will remind you of this every day. A passion for detail in design not only provides the foundation of El Zafiro but is the basis for every experience created and memory made here. The contemporary El Zafiro suite...
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    Simpson Bay, Sint Maarten
    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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    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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    Beachfront gated Condo directly on Simpson Bay1 / 17
    (4)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Waterfront
    • Grill
    • Air Conditioning
    • Washer
    • Ocean Views
    • 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
    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 designed to give...
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    Simpson Bay, Sint Maarten 00000
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Patio
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • DVD Player
    • Hot Tub
    • 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!Marisol is a light and airy St. Maarten vacation rental at Point Blue in Pelican Key Estate. With 2 bedrooms and 3 full bathrooms, this immaculate two storey townhouse provides a quiet and peaceful tropical oasis for your stay in...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    El Zafiro: Pearl Suite - Peace of mind!1 / 22
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Housekeeping Included
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 3, 2016
    Nice and clean! Good location right on the beach and also located near alot of other beaches, restaurants, bars and the airport. Nicole was very friendly and accommodating! She...
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    About this property
    Watch the sun rise and set from your own private patio or terrace, while enjoying the sunny warm weather and peaceful surrounding of St. Maarten. The contemporary design and facilities will serve your needs and desires during your stay with us. Queen sized bed provides a restful end of days spent...
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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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    • 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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    Simpson Bay, Sint Maarten SXM
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable and stylish with a beautiful view overlooking the pool area and marina of Porto Cupecoy, the apartment is air-conditioned throughout and has a spacious living room with elegant furniture and dining area with seating for 6. There is satellite TV, internet and a European-style kitchen...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • 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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
    • Housekeeping Included
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A perfect base for exploring the Maho and Simpson Bay area. Close enough to all the action but tucked away and secluded from it all. Watch the sun rise and set from your own private patio or terrace, while enjoying the sunny warm weather and peaceful surrounding of St. Maarten. The contemporary...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Coco Beach Club #16, a true beach front condo, located on the famous Simpson Bay Beach, near Maho and the famous night life that awaits! Imagine waking up in the morning and hearing the waves roll onto the beach from your private patio, then take in a walk right out onto the beach (you are 20 steps...
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    Simpson Bay, Sint Maarten SXM
    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
    • Satellite TV
    • DVD Player
    • Hot Tub
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Cool Bay Villa St Maarten1 / 21
    (16)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Grill
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • 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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    Simpson Bay, Sint Maarten 97150
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Washer
    • Satellite TV
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5 Bedroom Villa can be rented as a 2 or 3 Bedroom Villa at special rates! In a stunning waterfront location on the Simpson Bay lagoon, Villa Amaryllis is a luxurious fully air-conditioned, 5 bedroom residence, with its own boat dock and private pool overlooking the lagoon and the French...
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    Simpson Bay, Sint Maarten
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Simpson Bay Yacht Club Condo - Unit 61 / 18
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Satellite TV
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 17, 2017
    This is our 2nd time staying in Unit 6. We love the location, so close to a lot of good food and fun. Having a parking spot is a major plus, the pool area is nice and always...
    Reviewed February 8, 2015
    Very nice condo and better location. Clean with two nice bedrooms. Nice balcony and shared pool. Sam did great job with any question and the secure grounds are a nice feel good...
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    About this property
    WELCOME to Simpson Bay Yacht Club, our vacation home on beautiful St. Maarten island. Is this the right property for you? We understand that choosing the 'right' rental can be difficult and overwhelming. Here are some reasons why we enjoy staying in our unit. Location - Location - Location! Our...
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    Simpson Bay, Sint Maarten SXM
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located right on the beach in prestigious Pelican Key area on the Dutch side of St. Maarten lays IL Punto Blu. Convenience, spaciousness and panoramic views are the distinct advantages along with outstanding amenities at IL Punto Blu. Does the thought of crowded hotels and time-share sound...
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    Simpson Bay, Sint Maarten 97700
    Condo/Apartment - 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
    • 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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    Simpson Bay, Sint Maarten 00090
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Coral Breeze - STM1 / 16
    (3)Average
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 2, 2017
    I don't often write reviews like this but almost cried when I saw comments about "unit 8" on here, That review cannot be related to Coral Breeze as a long time yearly...
    Reviewed April 29, 2012
    This pair of houses is at a beautiful rocky beach just on the other side of the airport. We were worried that the close vicinity would be a problem, but remarkably it's not at...
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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 seagrape 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 11111
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Waterfront
    • Air Conditioning
    • Washer
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    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 open...
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    Simpson Bay, Sint Maarten 78866
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Caribbean Sun1 / 33
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Waterfront
    • 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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    • Ocean Views
    • Washer
    • Wi-Fi
    • DVD Player
    • Housekeeping Included
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Belle Villa at La Siesta Residence is an oceanfront, ground floor, 1 bedroom condo directly on Simpson Bay beach. It is on the Dutch side of St. Maarten/SXM in a quiet residential neighborhood conveniently located to restaurants, grocery stores, bakeries, shopping, water sports, casinos and the...
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    Simpson Bay, Sint Maarten SXM
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 97700
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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
    • 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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    Location Information
    Simpson Bay, Sint Maarten 00000
    Rental Home - 1 Bedroom, 1 Bathroom, 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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    Pet friendly
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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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    • Internet Access
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Directly on Sint Maarten’s Simpson Bay beaches, this luxurious studio guest house has everything you need for your vacation. This large studio is fully equipped with a full kitchen including a full size electric stove, microwave, refrigerator, dishwasher and Keurig coffee maker. A large walk in...
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    Simpson Bay, Sint Maarten
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    SIMPSON BAY BEACH CONDO #3...right on the beach at Simpson Bay1 / 14
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SBBC #3 is a 2 bedroom, 2 bath St. Maarten vacation rental located right on the beach at beautiful Simpson Bay. One of only 12 units in it's development, it offers quiet and comfortable surroundings, and the ocean just footsteps away in Dutch St. Maarten. The condo is located in a local...
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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Washer
    • Housekeeping Included
    • Grill
    • 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. The beach is...
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    Location Information
    Simpson Bay, Sint Maarten 1179
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • DVD Player
    • Housekeeping Included
    • Satellite TV
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury two bedroom unit at the prestigious Aqualina Beach Club directly on beautiful Simpson Bay beach. Unit 101 is the ideal property for one or two couples that love outdoor living and easy access to the beach and the turquoise Caribbean Sea. The unit is one of three in the complex of ten units...
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    Location Information
    Simpson Bay, Sint Maarten 99999
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful three bedroom, 3 ½ bath condo located in the Cupecoy area development known as Porto Cupecoy St. Maarten, close to French St. Martin-2 minutes drive to the border. Breathtaking view of Simpson Bay Lagoon and of romantic village marina and seaside piazza to the wide open panoramas of...
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    Simpson Bay, Sint Maarten 97700
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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
    Kid friendly
    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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Patio
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One Free Night (7 nights or more) - Travel from Aug 10 - Dec 15, 2017!Please inquire about lower rates offered for less than full occupancy.Villa 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...
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    Simpson Bay, Sint Maarten
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    Provence at Pelican Key, Saint Maarten - Ocean View, Pool, Lovely Outdoor1 / 39
    (1)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • DVD Player
    • Internet Access
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 28, 2015
    The excellent location in terms the security of Pelican Key, the views of this unit and its large size to accommodate large groups as ours made this a good choice.Even though...
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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
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for that one of a kind romantic hideaway on a fabulous beach without the huge price tag? You’ve found it! The Guest Cottage of Colony Manor Goldendaze sits directly on Sint Maarten’s beautiful soft white sandy beach, Simpson Bay. This luxurious, and oh so charming studio guest cottage has...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    5 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Satellite TV
    • Waterfront
    • Hot Tub
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    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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    Location Information
    Simpson Bay, Sint Maarten 78866
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Waterfront
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Washer
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Parking
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5 Bedroom Villa can be rented as a 2 or 3 Bedroom Villa at special rates! In a stunning waterfront location on the Simpson Bay lagoon, Villa Amaryllis is a luxurious fully air-conditioned, 5 bedroom residence, with its own boat dock and private pool overlooking the lagoon and the French...
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    Location Information
    Simpson Bay, Sint Maarten
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Waterfront
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Barefoot is an intimate, beachfront condo located on the water's edge of Simpson Bay Beach! This is a new, beautifully decorated 2 bedroom, 2.5 bath villa located directly on Simpson Bay Beach at Palm Beach Condos - a new intimate and well designed gated community of only twenty-four units, all...
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    Location Information
    Simpson Bay, Sint Maarten SX
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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