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Holiday Rentals near Random Wind

Skipjack's, Simpson Bay, St Martin / St Maarten
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    Travellers to Simpson Bay are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Simpson Bay
    Blue Pelican Luxury Villas - Featured on HGTV!!!!!1 / 14
    (29)Excellent
    0.4 miles from Random Wind
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Carisma on the beach1 / 22
    (19)Excellent
    0.5 miles from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    El Zafiro: Pearl Suite - Peace of mind!1 / 22
    (2)Excellent
    1.2 miles from Random Wind
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    El Zafiro: Ruby Suite - Unforgettable Getaway!1 / 23
    (2)Excellent
    1.2 miles from Random Wind
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Housekeeping Included
    • Ocean Views
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    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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    Simpson Bay Beach Modern Luxury Ocean View Private Roof Deck 360° views WIFI1 / 96
    (2)Very good
    0.5 miles from Random Wind
    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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    El Zafiro: Aquamarine Suite- Breathtaking views!1 / 22
    (1)Excellent
    1.2 miles from Random Wind
    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 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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    2BR-Oceanfront-Royal Palm1 / 10
    (4)Excellent
    0.0 miles from Random Wind
    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 15 May 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 14 February 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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Le Papillon - REOPENED AFTER IRMA - Modern Beachfront Unit with great view1 / 28
    (5)Excellent
    0.5 miles from Random Wind
    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 29 May 2018
    This condo is a great place to stay when visiting St. Maarten. The unit is right on the beach overlooking Simpson Bay. Many week days, we had the beach to ourselves. Also...
    Reviewed 25 June 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...
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    About this property
    Welcome in Le Papillon, we are the best maintained property on Simpson Bay beach. We recovered well from hurricane Irma and continue to provide the same quality accommodation as we did prior to Irma. THE UNIT INCLUDES: - Gated, private and secure community - 2150 sq. feet unit - Cleaning service...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW1 / 12
    (4)Very good
    0.6 miles from Random Wind
    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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    VILLA NICE LOVE  feet in water. Close to maho1 / 28
    (1)Excellent
    0.5 miles from Random Wind
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Private Garden
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 September 2016
    trip of a lifetimeMy friends and I had the trip of a lifetime to the beautiful Island of St Maarten. Our accommodations at beacon hill were amazing. The rooms were beautiful...
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    About this property
    This is a beautiful oceanfront 5 bedroom, 4 bathroom property that is located in a nice quiet area of Beacon Hill overlooking Burgeaux Bay on Dutch, St. Maarten.This villa offers amazing colors in the morning and unique sunsets. One of the characteristic of this villa is to be right on the beach,...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    BEACHFRONTBLISS1 / 30
    (1)Excellent
    0.3 miles from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Ocean Views
    • Terrace
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    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.3 miles from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bed Luxury Condo1 / 14
    (1)Excellent
    0.4 miles from Random Wind
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Ocean Views
    • Balcony
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    • Terrace
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    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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Le Papillon Penthouse - The most amazing beachfront property1 / 23
    (7)Excellent
    0.5 miles from Random Wind
    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 15 July 2018
    This was our first time visiting St. Martin and I admit I was a bit nervous renting Le Papillion. The pictures looked too good to be true. I’m happy to report that the rental...
    Reviewed 17 May 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 Penthouse, we are the best maintained property on Simpson Bay beach. We recovered well from hurricane Irma and continue to provide the same quality accommodation as we did prior to Irma. THE PENTHOUSE INCLUDES: - Gated, private & secure community - 3 floors - 4560 sq. feet...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    1.2 miles from Random Wind
    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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    0.3 miles from Random Wind
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Balcony
    • Sauna
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    1.2 miles from Random Wind
    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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.3 miles from Random Wind
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    ADVISEMENT: Please be advised that the Flamingo Beach Resort is closed from now through November 20, 2017. 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...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Cool Bay Villa St Maarten1 / 21
    (16)Excellent
    0.7 miles from Random Wind
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Grill
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 January 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 17 September 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.3 miles from Random Wind
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.1 miles from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Sauna
    • Balcony
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    Pet friendly
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    About this property
    ADVISEMENT: Royal Palm Beach Resort sustained extensive damage when Hurricane Irma made direct landfall on St. Maarten on Sept. 6, 2017 as a powerful Category 5 storm. Professional assessment teams determined the entire interior of the resort will need to be reconstructed. As a result, the resort...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.2 miles from Random Wind
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Terrace
    • Wi-Fi
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    • 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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    0.3 miles from Random Wind
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    About this property
    UNIT TYPE: The three bedroom penthouse unit features a King bed, two Queen size beds and a sleeper sofa. This unit can accommodate up to 8 guests. Also included are three bathrooms, a private balcony, washing machine, sitting and dining area, air conditioning and free Wifi. WASHING_MA, CONC,...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 BEDR townhouse overlooking OCEAN  ST- MAARTEN1 / 20
    (2)Excellent
    0.6 miles from Random Wind
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.2 miles from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Ocean Views
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Place Villa is an oceanfront, 2nd floor, 2 bedroom condo directly on the beach. It can be rented using 1 bedroom or two bedrooms (see the rates page for the additional cost when rented as a 2 bedroom). The one bedroom rental provides use of the entire villa and beachfront master bedroom...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Studio in Pelican Key Paradise1 / 11
    (1)Excellent
    0.2 miles from Random Wind
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Balcony
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    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 June 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
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.4 miles from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    • Washer
    • Ocean Views
    • Secure Parking
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This bautiful 2 bedroom, 2 bathroom beachfront condo offers stunning views of the Caribbean sea. The unit is situated on the 3rd floor of the building, overlooking Simpsonbay Beach. It features beach front common pool, and gated parking. This is a corner unit which makes the property even more...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.2 miles from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
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    • Grill
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Carib, a new spacious 2 bedroom, 2 bath beachfront Villa of 1700 sq. ft. is located directly on one of the most beautiful (2 1/2 mile ) beaches found anywhere in the Caribbean. Often referred to as the “best kept secret” on the island, Simpson Bay Beach is truly a “jewel” amongst St. Maarten’s...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Pelican Key 1Bedroom For Rent1 / 9
    (1)Excellent
    0.2 miles from Random Wind
    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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    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beachfront gated Condo directly on Simpson Bay1 / 16
    (5)Excellent
    0.4 miles from Random Wind
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Waterfront
    • Balcony
    • Air Conditioning
    • Patio
    • Ocean Views
    • Washer
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 February 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 7 January 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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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    0.2 miles from Random Wind
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Housekeeping Included
    • Ocean Views
    • DVD Player
    • 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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1.3 miles from Random Wind
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The property is located in the very in demand location called Beacon Hill. This property has 5 bedrooms and 5 bathrooms. The villas features huge dining and living room area. The property is fully equipped with wifi , BBQ grill for great outdoor moments. It also has cable Tv, washer and dryer and...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Anchorage Apartment1 / 18
    (2)Excellent
    0.2 miles from Random Wind
    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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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.3 miles from Random Wind
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1.2 miles from Random Wind
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Amazing View Penthouse apartment on Simpson Bay Beach  WE ARE BACK AFTER IRMA1 / 13
    (3)Excellent
    0.2 miles from Random Wind
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 February 2018
    The location is very convenient for the airport and has wonderful bars and restraunts close at hand. Kim the owner made sure we were comfortable with all the facilities. I hope...
    Reviewed 1 February 2018
    We came here for an extended Winter break. Fantastic beach side location. Easy walking distance (2 minutes) to Simpson bay restaurants and bars. Excellent, quality...
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    About this property
    Spacious Penthouse at La Siesta on the Simpson Bay Beach with truly amazing views. Two Bedrooms with en suite plus a Powder room. Master Bed has Four Poster King Size Bed on Beach side, Second Bed is Queen size both have en suites and each has a safe, with walk in showers, vessel sinks and...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    SMART VILLA...IRMA Survivor, stled beachfront at Pelican Key1 / 29
    (1)Excellent
    0.4 miles from Random Wind
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2015
    This condo was perfect. There were 3 huge bedrooms, a sizable living room area and 4 baths! The deck was perfect for relaxing and a few short steps down to the gorgeous beach...
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    About this property
    Please inquire about lower rates offered for less than full occupancy.Villa Smart is nestled beachfront at Pelican Key and offers a totally tropical, affordable family St. Maarten vacation rental with direct beach access and glorious ocean views, does not have a swimming pool....The terrace, full...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    0.7 miles from Random Wind
    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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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    0.7 miles from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located right on the beach at Simpson Bay, you will wake every morning to the sound of waves out the window. Coco Beach Club #5 is a 2 bedroom, 2 bathroom St Maarten Condo vacation rental that will have you coming back year after tear! Nicely decorated and very comfortable with gorgeous hardwood...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.4 miles from Random Wind
    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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    0.6 miles from Random Wind
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Garden
    • Secure Parking
    • Air Conditioning
    Suitability
    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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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.2 miles from Random Wind
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Outdoor Dining Area
    • Washer
    • Housekeeping Included
    • Balcony
    • Internet Access
    • Waterfront
    • Grill
    • Patio
    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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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Paradise Found at Las Arenas - Beachfront Luxury!1 / 17
    (10)Excellent
    0.5 miles from Random Wind
    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 4 February 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 30 November 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
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    1.3 miles from Random Wind
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7th Night Free7 night minimumMay 1 - October 31, 2018Please inquire about lower rates offered for less than full occupancy. Built on a cliff, directly above the tropical blue sea, Villa Tara offers vacationers a one of a kind experience. The backyard of this home is the majestic Caribbean Sea, and...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    The Blue Frenchie: Gorgeous 2-story townhouse in Pelican Key, St. Maarten1 / 19
    (1)Excellent
    0.4 miles from Random Wind
    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 11 May 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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    Location Information
    Simpson Bay, Sint Maarten
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    SIMPSON BAY BEACH CONDO #3...right on the beach at Simpson Bay1 / 14
    (1)Excellent
    0.3 miles from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Cable/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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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Villa Laluna1 / 24
    (2)Very good
    1.2 miles from Random Wind
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 July 2017
    The family of eight had a great time at Laluna villa. Private pool, on the beach, five minutes from the airport and walking distance to popular restaurants. Home does need some...
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    About this property
    Villa LaLuna is one of the few homes on this wonderful island of Sint Maarten that is located on the beach. The inviting home has 4 of its 5 bedrooms that give you spectacular ocean views. The villa is also in a great location because you are within walking distance to great entertainment ,...
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    Location Information
    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Coco Beach Duplex1 / 21
    (3)Average
    0.7 miles from Random Wind
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Washer
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 January 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 6 September 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...
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    Location Information
    Simpson Bay, Sint Maarten
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    0.4 miles from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Patio
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Dutch St. Maarten. Leave the hustle and bustle behind as you step...
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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit  on  a great beach!1 / 28
    (3)Excellent
    0.5 miles from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Waterfront
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Wi-Fi
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 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 20 December 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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    About this property
    7th Night Free7 night minimumMay 1 - October 31, 2018Please 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 Arenas in Sint Maarten, you know that this is a special...
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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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