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Holiday Rentals with Pools in Simpson Bay

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    Travellers to Simpson Bay are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    72 Matching Rentals in Simpson BayView all 107 rentals
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    Blue Pelican Luxury Villas - Featured on HGTV!!!!!1 / 14
    (29)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Carisma on the beach1 / 22
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2BR-Oceanfront-Royal Palm1 / 10
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cool Bay Villa St Maarten1 / 21
    (16)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Grill
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • 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 97150
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    VILLA NICE LOVE  feet in water. Close to maho1 / 28
    (1)Excellent
    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 0000
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Studio in Pelican Key Paradise1 / 22
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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 00014
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 BEDR townhouse overlooking OCEAN  ST- MAARTEN1 / 20
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2014
    I stayed at this villa with my family over the Christmas break. We had a fantastic time. My kids (10 and 7) enjoyed it very much. The place is very spacious and beatifully...
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    About this property
    Stylish , furnished 2 bedrooms, townhouse in quiet, residential area in Pelican, Rancho cielo Estates, Bathroom newly renovated with bath and rain shower, large master bedroom with furnished veranda with unobstructed ocean view. Walk-in closet. Very large open plan kitchen, courtyard with exotic...
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    Simpson Bay, Sint Maarten 000000
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Vacation Villa at Simpson's bay and Marina1 / 26
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Ocean Views
    • Housekeeping Included
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 February 2016
    I have stayed here 3 times and I am going back in Oct 2016 for TWO weeks! I am so thrilled w/this resort and rooms to stay in. The food is awesome and reasonably priced. The...
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    About this property
    Your home away from home on the Caribbean island of St. Maarten, is ideally positioned on the beach, midway between the island's most popular night spots and shopping. Fine Restaurants abound to tempt your pallet and an Activity Center makes it convenient for excursions to dive/snorkel spots along...
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    Simpson Bay, Sint Maarten 00000
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Coco Beach Duplex1 / 21
    (3)Average
    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 12 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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    Simpson Bay, Sint Maarten 11111
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Beachfront gated Condo directly on Simpson Bay1 / 16
    (5)Excellent
    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
    Beautifully decorated 2 bedroom, 2.5 bath villa located directly on Simpson Bay Beach at Palm Beach Condos on the Dutch Side of St. Maarten, a new intimate and well designed gated community of only twenty-four units, all facing both the pool and the beach beyond. The layout was designed to give...
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    Simpson Bay, Sint Maarten 00000
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Grill
    • Hot Tub
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're 2 couples or a small family looking for a bargain but don't want to compromise the 'cool factor' or your budget, then you've found your dream vacation spot! The Cliff House is a modern 2 bedroom, 2 bath oceanfront vacation villa perched on the cliffs of Beacon Hill overlooking the...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    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 N A
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Amazing View Penthouse apartment on Simpson Bay Beach  WE ARE BACK AFTER IRMA1 / 13
    (3)Excellent
    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 12345
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    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
    7th Night Free7 night minimumMay 1 - October 31, 2018Please 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...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Ocean Views
    • Cable/satellite TV
    • Housekeeping Included
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom, 2.5 Bath On The Water. Luxury At Its Best!!! This contemporary 5 star resort condo is now available for your enjoyment. Located on the ground floor this unit has an amazing spacious deck just steps from the waters' edge. Feel the breeze as you sip your coffee in the morning or enjoy a...
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    Simpson Bay, Sint Maarten 33023
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please inquire about lower rates offered for less than full occupancy.Practically roll out of bed on to the soft white sand of Simpson Bay beach!! Beachside is a very comfortably furnished 3 bedroom, 3 bath condo located directly on beautiful Simpson Bay beach! Beachside is the best located unit...
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    Simpson Bay, Sint Maarten 97150
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Ocean Views
    • Secure Parking
    • Balcony
    Suitability
    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 00000
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    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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    Simpson Bay, Sint Maarten 97150
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    The Blue Frenchie: Gorgeous 2-story townhouse in Pelican Key, St. Maarten1 / 19
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • Mountain Views
    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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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    Simpson Bay, Sint Maarten PELICAN KEY ST MAARTEN
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    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 SXM
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Washer
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please inquire about lower rates oered for less than full occupancy.Wow!! Stunning sunsets will captivate your heart at lovely villa “Belle Amour”... This beautifully rejuvenated, fully air-conditioned 5 bedroom, 4 bathroom oceanfront villa is located in a picturesque, quiet area of Beacon Hill...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 5 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Waterfront
    • Housekeeping Included
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coco's Beach #5 is a beautiful location for your vacation or stay in St. Maarten! Located right on the beach in Simpson Bay, you will wake every morning to the sights and sounds of the ocean. Living room and master bedroom have full ocean access with a large outdoor private deck. Enjoy the clean...
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    Simpson Bay, Sint Maarten 0000
    Condo/Apartment - 2 Bedrooms, 5 Bathrooms, Sleeps 6
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    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 97150
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pleas inquire about lower rates offered or less than full occupancy.Beautifully furnished, clean, spacious, and surprisingly affordable... If you are searching for your “Treasure Vacation”, look no further! Sea Beach Treasure is a lovely beachfront 2 BR, 2 BA Penthouse Condo (4th floor with...
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    Simpson Bay, Sint Maarten 97150
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This one bedroom townhouse is in one of the most desired areas on St Maarten. Pelican Key has bars, restaurants, beaches, and a casino, all within a 10 minute walk. The unit sets on the 2nd and 3rd floor of a small condo complex, with a shared swimming poo. The unit has some nice views from the...
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    Location Information
    Simpson Bay, Sint Maarten 000NA
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Caribbean Sun1 / 33
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 December 2016
    The entire property is very well maintained (pool and grounds were great, nice beach), and our condo had everything we needed. Terrific grocery shopping literally five minutes...
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    About this property
    This is a great property if you if you like low key with a fantastic view. Being in the middle of Simpson Bay you can walk a mile in either direction. The property has a great pool and the beach in front is never crowded. The owner has outfitted the unit with most everything to make your stay very...
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    Simpson Bay, Sint Maarten SAINT MARTIN
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    SIMPSON BAY BEACH CONDO #3...right on the beach at Simpson Bay1 / 14
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • 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 97150
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Paradise Found at Las Arenas - Beachfront Luxury!1 / 17
    (10)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Ocean Views
    • Housekeeping Included
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 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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    About this property
    HURRICANE IRMA UPDATE (September 30, 2017) Miraculously, Paradise Found was virtually unscathed but the building and grounds sustained some damage so I'm unable to take reservations at this time. I'm confident and optimistic that Las Arenas will return to it's elegant beauty by February 2018 and...
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    Simpson Bay, Sint Maarten 00000
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit  on  a great beach!1 / 14
    (3)Excellent
    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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    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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    Simpson Bay, Sint Maarten 97150
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful beachfront 5 bedroom, is located in the quiet area of Beacon Hill overlooking Burgaux Bay. Villa Hardman offers great views in the morning of the grand cruise ships and amazing colors during the sunsets. The villa is within walking distance to Maho which is one of the most popular...
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    Simpson Bay, Sint Maarten 0000 AA
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    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 97150
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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 97150
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!1 / 13
    (3)Very good
    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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    7th Night Free7 night minimumMay 1 - October 31, 2018Please 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...
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    Simpson Bay, Sint Maarten 97150
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Villa Vita on the beach St Maarten,Caribbean1 / 33
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 January 2017
    We had very high expectations for our trip since we had visited St. Maarten before and we were not disappointed. We had read it was in a new development with some construction...
    Reviewed 5 January 2017
    We brought our family (4 children, 2 adults) to St Maarten and elected to rent a Villa instead of staying at the Royal Palm (we have stayed here many times). We have been to...
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    About this property
    A beautiful new house in a new development, within a quiet gated community, with security onsite. Yet it is just a few minutes to great restaurants, duty free shopping, casinos, spas and grocery stores. And only 10 minutes from Princess Julianna Airport. Our 3 bedroom house comfortably sleeps 6...
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    Simpson Bay, Sint Maarten NA
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
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    • 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 97150
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Wi-Fi
    • Housekeeping Included
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique, romantic, comfortable STUDIO in beautiful residential area completely equipped with linens, AC, TV, cable, Wi-Fi, kitchenette, pool, parking right in front. Quiet location with easy access to restaurants, entertainment, beach, casino. water sports, <BR>Airport is within 10...
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    Simpson Bay, Sint Maarten 0000
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Pelican Key 1Bedroom For Rent1 / 9
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Internet Access
    • Cable/satellite TV
    • Balcony
    • Terrace
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1 bedroom/1bath unit is located in Pelican Key/Simpson Bay' next to LaVista Resort. Within walking distance to many restaurants, bars, grocery store and casino. The unit has a full kitchen with all the comforts of home, a futon sleeper sofa and cot downstairs for 2 and a bedroom with a king...
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    Simpson Bay, Sint Maarten 00090
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    CASA DE BELLA... Great location at a great price!!1 / 23
    (2)Very good
    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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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Waterfront
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Barefoot is an intimate, beachfront condo located on the water's edge of Simpson Bay Beach! This is a new, beautifully decorated 2 bedroom, 2.5 bath villa located directly on Simpson Bay Beach at Palm Beach Condos - a new intimate and well designed gated community of only twenty-four units, all...
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    Simpson Bay, Sint Maarten SX
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    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 SXM
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    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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    Simpson Bay, Sint Maarten 000AA
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    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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    Simpson Bay, Sint Maarten 0000AA
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    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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    Simpson Bay, Sint Maarten 97150
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Washer
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'At Seaside' is our dream...make it yours too! Serene Caribbean views can be enjoyed from the terrace. She is one of 20 units in a gated community surrounding a pool with views of the Caribbean. The grounds are lush and well tended. There is a king-sized bed and master bath off the bedroom. There...
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    Simpson Bay, Sint Maarten 000
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    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 99999
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built on 3 levels, the villa’s immaculate interior spaces include a ground floor, well-equipped and welcoming kitchen, a spacious dining area with a long table easily able to seat 10/12 people and an impressive home cinema with seating for 8. The 2nd floor houses 3 large bedroom suites with king...
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    Simpson Bay, Sint Maarten 00000
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    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
    7th Night Free, 7 night minimum for travel May 1 - October 31, 2018Please 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...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    WITENBLAUW... Magical Beach Front Estate on Pelican Key1 / 61
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    COCO BEACH CLUB 6...walk right out onto the beach at Simpson Bay1 / 20
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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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    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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    Beach Heaven1 / 5
    (1)Terrible
    2 Bedrooms, 6 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Waterfront
    • Mountain Views
    • Air Conditioning
    • DVD Player
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a magnificent penthouse condominium right on golden sand Simpson Bay Beach. This is a two kilometer (1 1/4 mile) stretch of sand and Caribbean sea that is completely secluded - only private residences and small guest houses. As a result, you have an unspoiled, non-commercial beach all to...
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    Simpson Bay, Sint Maarten NONE
    Condo/Apartment - 2 Bedrooms, 6 Bathrooms, Sleeps 4
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