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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
    0.6 kilometres from Random Wind
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Simpson Bay Beach Modern Luxury Ocean View Private Roof Deck 360° views WIFI1 / 32
    (2)Very good
    0.9 kilometres from Random Wind
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Le Papillon - REOPENED AFTER IRMA - Modern Beachfront Unit with great view1 / 24
    (4)Excellent
    0.8 kilometres from Random Wind
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Le Papillon Penthouse - The most amazing beachfront property1 / 24
    (6)Excellent
    0.8 kilometres 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 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...
    Reviewed 26 April 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, 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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    PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW1 / 12
    (4)Very good
    0.9 kilometres 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 13 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 8 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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    2 BEDR townhouse overlooking OCEAN  ST- MAARTEN1 / 20
    (2)Excellent
    1.0 kilometres 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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    Carisma on the beach1 / 22
    (15)Excellent
    0.8 kilometres from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Housekeeping Included
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Charisma on the beach was fabulous! Great location in Pelican Key, beautiful villa with everything we needed and more! Paul and Carmen went far beyond to make us feel special...
    Reviewed 20 August 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...
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    El Zafiro: Aquamarine Suite- Breathtaking views!1 / 22
    (1)Excellent
    2.0 kilometres 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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    El Zafiro: Pearl Suite - Peace of mind!1 / 22
    (2)Excellent
    2.0 kilometres from Random Wind
    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 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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    El Zafiro: Ruby Suite - Unforgettable Getaway!1 / 23
    (1)Excellent
    2.0 kilometres 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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    2BR-Oceanfront-Royal Palm1 / 10
    (4)Excellent
    0.1 kilometres 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 15 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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    Amazing View Penthouse apartment on Simpson Bay Beach  WE ARE BACK AFTER IRMA1 / 13
    (3)Excellent
    0.4 kilometres 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 2 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 2 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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    Pelican Key 1Bedroom For Rent1 / 9
    (1)Excellent
    0.4 kilometres 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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    2.0 kilometres from Random Wind
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Housekeeping Included
    Suitability
    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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    0.9 kilometres from Random Wind
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Wi-Fi
    • Children's Pool
    • Washer
    • Parking
    • 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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    BEACHFRONTBLISS1 / 15
    (1)Excellent
    0.6 kilometres from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Ocean Views
    • Terrace
    • Patio
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ◾first floor direct access to the pool and beachfront ◾amazing 3 ½ mile crescent of powdery white sand beach with gentle waves ◾private pool front lanai accessible from the master bedroom and living area ◾large, fully functional kitchen, all granite ,new, top grade appliances and all kitchen...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bed Luxury Condo1 / 14
    (1)Excellent
    0.7 kilometres from Random Wind
    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
    Reviewed 7 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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    Cool Bay Villa St Maarten1 / 21
    (16)Excellent
    1.2 kilometres 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 11 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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    1.1 kilometres from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • 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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    Anchorage Apartment1 / 18
    (2)Excellent
    0.3 kilometres 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 1 May 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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    COCO BEACH CLUB 6...walk right out onto the beach at Simpson Bay1 / 20
    (1)Excellent
    1.1 kilometres from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 April 2017
    We've been vacationing in St. Maarten for over 25 years and have had the pleasure of staying in many beautiful villas and hotels. We were back for the 2nd time to Coco Beach...
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    About this property
    A Wonderful Place!!! Coco Beach Club #6 beach front St. Maarten vacation rental, Dutch St Maarten , Simpson Bay Beach, near Maho night life.Wake up in the morning and walk right out onto the beach at Simpson Bay when you stay at this new 2 bedroom 2 bath St Maarten rental condo. Coco Beach #6 has...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.4 kilometres from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Carib, a new spacious 2 bedroom, 2 bath beachfront Villa of 1700 sq. ft. is located directly on one of the most beautiful (2 1/2 mile ) beaches found anywhere in the Caribbean. Often referred to as the “best kept secret” on the island, Simpson Bay Beach is truly a “jewel” amongst St. Maarten’s...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1.2 kilometres from Random Wind
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Wi-Fi
    • Housekeeping Included
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique, romantic, comfortable STUDIO in beautiful residential area completely equipped with linens, AC, TV, cable, Wi-Fi, kitchenette, pool, parking right in front. Quiet location with easy access to restaurants, entertainment, beach, casino. water sports, <BR>Airport is within 10...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2.0 kilometres from Random Wind
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This one bedroom condo unit is located in beacon hill on the ocean with views from both sides of the unit. You are within shorts distance and even walking distance should I say to great beaches such as the simpson bay beach or mullet bay beach, to restaurants, casinos, bars and any other...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    0.5 kilometres from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Simpson Bay Beach Condo #2 is a beautiful ground floor, well equipped, fully air-conditioned condo located directly on Simpson Bay Beach. Walk off your patio and onto a wonderful soft sandy beach! Enjoy quiet mornings with the birds singing or take an early morning stroll or dip on beautiful, two...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.6 kilometres 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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    SIMPSON BAY BEACH CONDO #3...right on the beach at Simpson Bay1 / 14
    (1)Excellent
    0.6 kilometres 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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    CARIBBEAN BLUE... IRMA Survivor 5BR beachfront home in Pelican Key1 / 32
    (1)Excellent
    0.7 kilometres from Random Wind
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please inquire about lower rates offered for less than full occupancy. Welcome to Caribbean Blue!! If you’re looking for a large affordable beachfront villa for a group of couples or a family reunion, you’ve found it! Located in one of St Maarten’s most popular areas, the charming community of...
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    Location Information
    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Studio in Pelican Key Paradise1 / 11
    (1)Excellent
    0.4 kilometres from Random Wind
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.7 kilometres from Random Wind
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Sapphire, the perfect vacation home, is a charming Caribbean styled house nestled in lush tropical gardens. Sitting high on a hillside in the exclusive Pelican Key area, the house offers wonderful views of the Caribbean Sea and St. Maarten’s spectacular sunsets. Each of the...
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    Location Information
    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Survived Irma!!  Beachfront gated Condo directly on Simpson Bay1 / 16
    (5)Excellent
    0.7 kilometres 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 15 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
    Survived Irma!! Beautifully decorated 2 bedroom, 2.5 bath villa located directly on Simpson Bay Beach at Palm Beach Condos on the Dutch Side of St. Maarten, a new intimate and well designed gated community of only twenty-four units, all facing both the pool and the beach beyond. The layout was...
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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    UNFORGETTABLE... IRMA Survivor!! Beachfront contemporary condo on fabulous beach1 / 13
    (3)Very good
    0.9 kilometres from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Hot Tub
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 November 2013
    The beach was lovely the service at the beach and st the resort restaurants was great. There were places to go downtown. The prearranged trip downtown with one of the major...
    Reviewed 15 July 2013
    Our family of 3 spent a week in Unforgettable. It lives up to its name. The location is perfect, right on the beach in Simpson Bay. Our daughter is disabled and in a wheelchair...
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    About this property
    Please inquire about lower rates offered for less than full occupancy. 'Unforgettable' is two bedroom, two and a half bathroom ground floor luxury St. Maarten vacation rental condo... is located in Las Arenas, a new contemporary, high quality complex on Simpson Bay Beach. The disappearing sliding...
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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.6 kilometres from Random Wind
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Washer
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Construction around property! Please inquire about lower rates offered for less than full occupancy Located right on the beach in prestigious Pelican Key area on the Dutch side of St. Maarten lays Il Punto Blue. Convenience, spaciousness and panoramic views are the distinct advantages along with...
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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    0.8 kilometres from Random Wind
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Parking
    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please inquire about lower rates offered for less than full occupancy.Sapphire villa, the perfect St. Maarten vacation rental, is a charming Caribbean styled house nestled in lush tropical gardens. Sitting high on a hillside in the exclusive Pelican Key area. The villa offers wonderful views of the...
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    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    SMART VILLA...IRMA Survivor, stled beachfront at Pelican Key1 / 29
    (1)Excellent
    0.7 kilometres 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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    Location Information
    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    RENDEZVOUS... IRMA Survivor!! A fabulous 2 BR contemporary 2 BR condo unit  on1 / 14
    (3)Excellent
    0.9 kilometres from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • 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 15 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 21 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
    Please 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 place. Elevator accessible and features 2 king-size...
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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1.0 kilometres from Random Wind
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Patio
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Terrace
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just Blue is a beautiful penthouse on the Simpson Bay Lagoon. This contemporary & modern penthouse has a beautiful view of the Simpson Bay Lagoon and the Caribbean sea. The many yachts moored in the surrounding marinas offer a glittering view, both by day and night. Located on the 4th floor, with...
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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2.0 kilometres from Random Wind
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    VILLA VISTA – The name says it all!! This magnificent 5 bedroom 6 bath luxury Villa features stunning panoramic views from virtually every room and every angle! Villa Vista features 3 large suites on the main floor in addition to 2 private studio suites on the lower level with both studios...
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    Location Information
    Simpson Bay, Sint Maarten
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    0.7 kilometres from Random Wind
    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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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    1.2 kilometres 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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    CASA DE BELLA... IRMA Survivor!! great location at a great price!!1 / 23
    (2)Very good
    0.5 kilometres from Random Wind
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 February 2015
    We decided to rent a villa/house instead of staying in a all-inclusive because we were a group of 5 friends to enjoy a more local experience. We were situated in Simpson Bay...
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    About this property
    CASA DE BELLA is a very comfortable, fully air-conditioned 3 bedroom, 2 ½ bath townhome with views towards Simpson Bay and the Simpson Bay Lagoon... and it has a private pool! It is conveniently located in Simpson Bay and is an easy, short walk to a plethora of shopping, beaches (Kim Shaw is just...
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    Location Information
    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.5 kilometres from Random Wind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
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    • DVD Player
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    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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    Location Information
    Simpson Bay, Sint Maarten
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.7 kilometres from Random Wind
    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
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please inquire about lower rates offered for less than full occupancy.Villa Bisou du Soleil is a lovely, very spacious St. Maarten vacation villa rental, located high on the hillside at Pelican Key, with an unobstructed view of the Caribbean Sea from every room.Each room opens to the patio which...
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    Location Information
    Simpson Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.6 kilometres from Random Wind
    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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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.6 kilometres 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
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    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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    1.0 kilometres from Random Wind
    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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.8 kilometres from Random Wind
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Air Conditioning
    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please inquire about lower rates offered for less than full occupancy. Villa Provence enjoys a majestic view from its elevated location up on the Pelican Key and offers breathtaking sunsets every evening. Imagine watching the sun set with a delicious local cocktail in hand while in your private...
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    Location Information
    Simpson Bay, Sint Maarten
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    2.0 kilometres from Random Wind
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely ocean edge condominium is located in a nice and peaceful neighborhood of Beacon Hill. Within 10 min walking distance from all attractions of the famous MAHO bay: beaches, restaurants, bars, casinos, nightclubs, grocery stores and druggist. Enjoy the sunrise on the front porch, sunset...
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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    0.6 kilometres 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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    WITENBLAUW... Irma Survivor, Magical Beach Front Estate on Pelican Key1 / 61
    (1)Excellent
    0.6 kilometres from Random Wind
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 2015
    Well worth the money!! Not only was the estate exactly as pictured, the housekeeping and grounds staff was terrific as well. We will definitely be returning.....
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    About this property
    Witenblauw Estate is a magnificent, sprawling 6 bedroom paradise built for entertaining and relaxation! If a picture is worth a thousand words then Witenblauw speaks volumes when it comes to making memories of a lifetime. This ocean side retreat redefines the traditional get-a-way vacation...
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    Location Information
    Simpson Bay, Sint Maarten
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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