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Cheap Simpson Bay Holiday Rentals

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    Travellers to Simpson Bay are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    26 Matching Rentals in Simpson BayView all 105 rentals
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    El Zafiro: Ruby Suite - Unforgettable Getaway!1 / 23
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Cool Bay Villa St Maarten1 / 21
    (16)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renewed and fully equipped suite, beautiful furnitures, excellent mattress, terrace view of Simpson Bay and the Caribbean. Good cleaning service. White powder sand & clear water to feel cool all the holidays long. Bath towels. Entièrement rénové et totalement équipée suite, beau mobilier,...
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    Simpson Bay, Sint Maarten 97150
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Saturday Dec 15, 2018 to Saturday Dec 22, 2018 Luxurious one-bedroom villa overlooking Kim Shaw Beach on the 7th floor of The Atrium Beach Resort. Great views day & night .. watch the sunset right from your awesome balcony. Located in Simpson Bay on the Dutch side. Fully equipped kitchen with...
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    Simpson Bay, Sint Maarten 13041
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    • Balcony
    • DVD Player
    • Patio
    • Ocean Views
    • Grill
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 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 7 August 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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated in Simpson Bay you will find this cozy 1 bedroom apartment. This apartment is at 15 steps from the beach and at 10 minutes walking distance of restaurants/bars/casinos/activities. Enjoy all that we offer! The apartment (separate building) has 1 bedroom with a king size bed. There is a...
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    Simpson Bay, Sint Maarten SXM
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    • Private Garden
    • Wi-Fi
    • Children's Pool
    • Washer
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    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renovated condo in Pelican Key. Walk to beach nite life resturants,casino grocery store Pool in back. Safe and quit area in Pelican key. Local contact to help with any special needs. If needed attached newly renovated studio with Queen bed separate ac ,tv/cable and internet. New tiled...
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    Simpson Bay, Sint Maarten 99999
    Condo/Apartment - 1 Bedroom, 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 23 February 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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 30 April 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 12 April 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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    Simpson Bay, Sint Maarten 11111
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful beachfront 5 bedroom, is located in the quiet area of Beacon Hill overlooking Burgaux Bay. Villa Hardman offers great views in the morning of the grand cruise ships and amazing colors during the sunsets. The villa is within walking distance to Maho which is one of the most popular...
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    Simpson Bay, Sint Maarten 0000 AA
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Simpson Bay Beach Modern Luxury Ocean View Private Roof Deck 360° views WIFI1 / 32
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Ocean Views
    • DVD Player
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 February 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 17 January 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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    1 Bed Luxury Condo1 / 14
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Ocean Views
    • Balcony
    • Grill
    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 February 2018
    Beautiful quiet and immaculate. The pool was just outside the door. Nice patio overlooking the ocean. Beautiful Modern kitchen and bath room. Very secure. No worries. Gladly...
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    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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Housekeeping Included
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bedroom condo fully equipped with daily maid service for your stay on the beautiful and friendly island of St. Maarten. It is located conveniently by the airport on Simpson Bay with its own private beach. Enjoy your free chairs and umbrellas with bar services available on the beach.Your condo...
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    Simpson Bay, Sint Maarten 48439
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Blue Pelican Luxury Villas - Featured on HGTV!!!!!1 / 14
    (29)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2017
    This Villa is the ideal place for a couple to stay.It has every updated amenity you need on an island vacation. Garo the owner is great and on-site manager Theresa is wonderful...
    Reviewed 24 June 2017
    Lovely 2 story apartment located in a beautifully manicured garden setting. We could see the sea from the balcony on the second floor. It was tastefully appointed with...
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    About this property
    Travelers Choice Award for 2012 - 2017 and Rated Best Vacation rental in St. Maarten for 2017, Blue Pelican Villas is located on the Dutch side of St. Maarten in the exclusive area of Pelican Key. Blue Pelican is a spacious 1 bedroom villa set on an upscale property with a wonderful interior garden...
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    Simpson Bay, Sint Maarten PELICAN KEY
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Indulge yourself in this peaceful beach front retreat, and get ready to fulfill all your getaway desires. Refresh and renew your spirit with spectacular panoramic views of the pristine Caribbean sea. As you walk through the front door your eyes are immediately drawn through the living space out...
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    Simpson Bay, Sint Maarten 000
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    About this property
    _________________________ ABOUT THE UNIT ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯ This newly renovated vacation rentals can sleep up to 4 guests and features a private balcony with Caribbean views. It also includes a kitchen, perfect for preparing a quick meal between activities. WASHING_MA, CONC, FITNESSRM, BA,...
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    Simpson Bay, Sint Maarten 29572
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Terrace
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    • Secure Parking
    Suitability
    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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    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
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    Pet friendly
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    Smoking allowed
    Reviewed 4 October 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 4 Quick View
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    • Ocean Views
    • Terrace
    • Balcony
    • Housekeeping Included
    • Patio
    • DVD Player
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RENTAL 2/11/2017 2/18/2017 Week 6 Simpson Bay Resort Beautiful 1 bedroom with 2 murphy beds comfortably sleeps 4. Newly renovated, in Caladium Building, features King Bedroom with flat screen TV, free internet, large closets, full kitchen with large counter space and full size appliances, dining...
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    Simpson Bay, Sint Maarten NONE
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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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    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
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    • Secure Parking
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Balcony
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    • Terrace
    • Housekeeping Included
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Boundless ocean views for miles with stylish-appointed state of the art suites to ensure peace and tranquility while promising rest and relaxation. EL Zafiro is an unforgettable luxury at the heart of one of the Caribbean's most glamorous beaches. This meticulously designed suite represents one of...
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    Simpson Bay, Sint Maarten 000
    Condo/Apartment - 1 Bedroom, 1 Bathroom, 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 2 January 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    About this property
    ADVISEMENT: April 2018: Demolition is in progress and moving along smoothly. Floor tiles are being removed from almost every unit in Building 7, which is the only building currently connected to city power. New metal roofing has been installed on Buildings 3 and 4, and the engineering building...
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    Simpson Bay, Sint Maarten 00000
    Condo/Apartment - 1 Bathroom, 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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