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Simpson Bay Vacation Rentals

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    Travelers to Simpson Bay are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 214 Rentals in Simpson Bay
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    Carisma on the beach1 / 22
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Blue Pelican Luxury Villas - Featured on HGTV!!!!!1 / 12
    (27)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Le Papillon - Modern Beachfront Unit, stunning view, great amenities1 / 24
    (3)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Villa Velaire, Oceanfront Villa with Private Pool1 / 22
    (7)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Waterfront
    • Satellite TV
    • Housekeeping Included
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 8, 2016
    Villa Velaire was exactly as advertised. Kim was amazing to work with and made sure our stay was perfect!! My husband and I traveled with our good friends and the house was...
    Reviewed April 19, 2016
    My wife & I have been to St. Martin multiple times and each time have rented a different villa. Villa Velaire is by far and away the best rental we have found. The owner is...
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    About this property
    Located in a private gated community, perched along the ocean cliffs in Pelican Key (just above Simpson Bay) St Maarten, stands Villa Velaire - a private two bedroom/2.5 bath rental villa. The Villa, recently renovated and completely redecorated in September of 2013, uses an eclectic mix of British...
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    Simpson Bay, Sint Maarten 00000
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW1 / 12
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Grill
    • Satellite TV
    • DVD Player
    • Ocean Views
    • Patio
    • Wi-Fi
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 13, 2015
    I stayed here for 2 weeks and soon began to really feel at home. The unit has everything it needs and the large patio with table is a real gem in the mornings and evenings...
    Reviewed May 15, 2015
    If you are looking for a home away from home, this is the place! This appartment is very well located on the Dutch side of the island in a very quiet and safe neighborhood. It...
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    About this property
    Spacious studio apartment with breathtaking views for rent. Located on the island of St. Maarten in the heart of the Caribbean, this fully equipped studio, located a few minutes from all amenities is your perfect tropical getaway.Enjoy our beautiful island at its best and relax at the end of a full...
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    Simpson Bay, Sint Maarten 99999
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Housekeeping Included
    • Terrace
    • Satellite TV
    • Wi-Fi
    • Patio
    • Secure Parking
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 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
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Housekeeping Included
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 3, 2016
    Nice and clean! Good location right on the beach and also located near alot of other beaches, restaurants, bars and the airport. Nicole was very friendly and accommodating! She...
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    About this property
    Watch the sun rise and set from your own private patio or terrace, while enjoying the sunny warm weather and peaceful surrounding of St. Maarten. The contemporary design and facilities will serve your needs and desires during your stay with us. Queen sized bed provides a restful end of days spent...
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    Simpson Bay, Sint Maarten SINT MAARTEN
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2BR-Oceanfront-Royal Palm1 / 10
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Ocean Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 15, 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 February 14, 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 00SXM
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Le Papillon Penthouse - Stunning, modern beachfront unit with private roof top1 / 24
    (6)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Ocean Views
    • Satellite TV
    • Mountain Views
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 17, 2017
    We have been coming to St. Martin for the past 14 years and this time we brought the whole family with us. We rented both the penthouse and the 2 bedroom unit at the same time...
    Reviewed April 25, 2017
    Just returned home from a fantastic 10 night stay at the beautiful Le Papillion penthouse. Everything was perfect! We arrived at the villa and we were greeted by Simona, our...
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    About this property
    Welcome in Le Papillon Penthouse, the best experience on Simpson Bay beach. - Gated, private & secure community - 3 floor penthouse - 4560 sq. feet unit - Cleaning service every second day - Roof terrace with long chairs, dining area, summer kitchen and 360 degrees view - Private jacuzzi on the...
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    Simpson Bay, Sint Maarten 00000
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Simpson Bay Beach Modern Luxury Ocean View 1 BR1 / 32
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Grill
    • Ocean Views
    • DVD Player
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 8, 2014
    Apartment is private, has all new appliances, including washer and dryer and dish washer. Hot water is freely available (not always true on every island we've stayed at...
    Reviewed January 17, 2014
    This private residence is located in a quiet residential area with a wonderful host. It has everything you need and is centrally located close to a large grocery store and...
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    About this property
    Modern 1 bedroom apartment newly built. Marble floors through out. All stainless steel appliances in kitchen and granite counter top. Hi speed WiFi internet. Dish Network Satellite TV in living room and bedroom. Air conditioning in all areas. Very private due it being a single detached apartment...
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    Location Information
    Simpson Bay, Sint Maarten NA
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    BEACHFRONTBLISS1 / 15
    (1)Excellent
    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 NONE
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 BEDR townhouse overlooking OCEAN  ST- MAARTEN1 / 20
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 2, 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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    Location Information
    Simpson Bay, Sint Maarten 000000
    Rental Home - 2 Bedrooms, 1 Bathroom, 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
    • Internet Access
    • Satellite TV
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 9, 2017
    We had very high expectations for our trip since we had visited St. Maarten before and we were not disappointed. We had read it was in a new development with some construction...
    Reviewed January 5, 2017
    We brought our family (4 children, 2 adults) to St Maarten and elected to rent a Villa instead of staying at the Royal Palm (we have stayed here many times). We have been to...
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    About this property
    A beautiful new house in a new development, within a quiet gated community, with security onsite. Yet it is just a few minutes to great restaurants, duty free shopping, casinos, spas and grocery stores. And only 10 minutes from Princess Julianna Airport. Our 3 bedroom house comfortably sleeps 6...
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    Simpson Bay, Sint Maarten NA
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Vacation Villa at Simpson's bay and Marina1 / 26
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • DVD Player
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Ocean Views
    • Housekeeping Included
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 23, 2016
    I have stayed here 3 times and I am going back in Oct 2016 for TWO weeks! I am so thrilled w/this resort and rooms to stay in. The food is awesome and reasonably priced. The...
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    About this property
    Your home away from home on the Caribbean island of St. Maarten, is ideally positioned on the beach, midway between the island's most popular night spots and shopping. Fine Restaurants abound to tempt your pallet and an Activity Center makes it convenient for excursions to dive/snorkel spots along...
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    Location Information
    Simpson Bay, Sint Maarten ST MAARTEEN DWI
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Perfect Pelican Escape -- Spectacular Views & Best Sunset Happy Hour1 / 17
    (5)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Ocean Views
    • Satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 13, 2016
    We recently returned from a three-week stay at this Penthouse and we give it an "A Plus" rating. The property is lovely, and exactly as shown in the photos. It is very...
    Reviewed February 7, 2014
    I really enjoyed staying at this condo. The location was very convienent and the condo had all of luxuries of home! (Really nice). The view from the balcony was priceless...
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    About this property
    Nestled on top of Pelican Key on Sint Maarten is Son Risa Penthouse; where spectacular views of of the Caribbean Sea await you. This tropical oasis is set just far enough from the entertainment neighborhood to allow for quiet relaxation while still with in walking distance of restaurants, bars,...
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    Simpson Bay, Sint Maarten SXM
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sur Mer is a beachfront condo, located on Simpson Bay Beach in the Coco Beach complex! This great 3 bedroom – 3 bath beautiful St Maarten condo is the perfect rental for your vacation! Sur Mer has every amenity for a comfortable stay: including central air, satellite TV, WiFi, and maid service. The...
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    Location Information
    Simpson Bay, Sint Maarten 78866
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Internet Access
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    La-di-da is a gorgeous, contemporary 4 bedroom, 4 bath villa with a 2 bedroom apartment located below the main part of the villa that sits high atop a hill at the mouth of Pelican Key. This setting provides wonderful privacy at the villa. From the living areas, decks and pool area you are...
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    Simpson Bay, Sint Maarten 78866
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Studio in Pelican Key Paradise1 / 11
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 18, 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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    Cool Bay Villa St Maarten1 / 21
    (16)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Grill
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 10, 2016
    We rented this adorable villa with our two teenage kids for a Caribbean Christmas Vacation. The beginning of our vacation didn't start off so well. The owners were out of town...
    Reviewed September 17, 2014
    Go!! For tomorrow is later. Near there supermarket, and drugs. The Maho Beach is near in car too. Near there Dominican food, no is so expensive.
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    About this property
    Rigth next to St Maarten' s Lagoon - A lovely setting, surrounded by trees and plants. Just a short 2 miles hop to the beach, this traditional Caribbean (65m2) villa is ideal for a family. Fully air-conditionned,it has a terrace and a balcony with garden furniture, including hammock, parasol and...
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    Simpson Bay, Sint Maarten 97150
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Anchorage Apartment1 / 18
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Ocean Views
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 30, 2016
    Loved Martine's apartment! It is right across the road from the beach and close to all the sights and ammenities in Simpson Bay. Martine was excellent to deal with and she made...
    Reviewed April 12, 2015
    This is a return trip to this apartment, that is how much we have liked it in the past. This trip again, we had a wonderful time. The apartment is is big enough for 4, with all...
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    About this property
    Beautiful beach side apartment with spectacular ocean view in Simpson Bay.<BR>Come stay and enjoy the beautiful sunsets and relax on the beach!<BR>Surrounded by top rated restaurants, bars, supermarkets, casino's and nightlife.<BR>Private car parking.<BR>Child friendly.<BR>Fully equipped apartment,...
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    Simpson Bay, Sint Maarten 11111
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Paradise Found at Las Arenas - Beachfront Luxury!1 / 18
    (10)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Ocean Views
    • Housekeeping Included
    • Wi-Fi
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 4, 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 November 30, 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
    One of the most luxurious beach-front residences in Dutch Sint Maarten, Paradise Found is located on beautiful Simpson Bay. Located directly on a secluded two-mile white sand beach, this exquisite two-bedroom villa is part of elegant Las Arenas, a new, attractively-appointed twelve-unit building...
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    Location Information
    Simpson Bay, Sint Maarten 00000
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Washer
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built on a cliff, directly above the tropical blue sea. The luxury rental Villa Tara offers vacationers a 'one of a kind' experience. The backyard of this home is the majestic Caribbean Sea, and it can be admired from almost every room in this villa. Cleverly designed pocket doors allow you to open...
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    Location Information
    Simpson Bay, Sint Maarten 78866
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Waterfront
    • Wi-Fi
    • Housekeeping Included
    • Air Conditioning
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This brand new 2 bedrooms, 2 bath villa is located in Beacon Hill on the Cliffside overlooking the stunning Simpson Bay Beach. This villa has a very private pool area with mazing views on the ocean. The Front part of the property is great at night to enjoy the colorful sunsets.  The property is...
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    Location Information
    Simpson Bay, Sint Maarten 9999 XX
    Rental Home - 2 Bedrooms, 2 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
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SBBC #3 is a 2 bedroom, 2 bath St. Maarten vacation rental located right on the beach at beautiful Simpson Bay. One of only 12 units in it's development, it offers quiet and comfortable surroundings, and the ocean just footsteps away in Dutch St. Maarten. The condo is located in a local...
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    Location Information
    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beachfront gated Condo directly on Simpson Bay1 / 17
    (4)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Waterfront
    • Grill
    • Air Conditioning
    • Washer
    • Ocean Views
    • Satellite TV
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 14, 2017
    We spent a week at Kelly and EJs beautiful condo at The Palms.This condo is spacious, bright and inviting. There is everything from a full kitchen, beach towels, information...
    Reviewed January 7, 2015
    We recently rented a 1 bedroom at Simpson Bay Resort. Although we were in the older building that was in need of some updating we were very pleased with the size of our room...
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    About this property
    Beautifully decorated 2 bedroom, 2.5 bath villa located directly on Simpson Bay Beach at Palm Beach Condos on the Dutch Side of St. Maarten, a new intimate and well designed gated community of only twenty-four units, all facing both the pool and the beach beyond. The layout was designed to give...
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    Location Information
    Simpson Bay, Sint Maarten 00000
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Ocean Views
    • Balcony
    • Grill
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful 1 bedroom Condo is set high up on Pelican key. It is Quiet secluded and only 5 minutes walk from the beach. Its very modern, clean and luxurious. A perfect quiet secluded hideaway! All amenities are close by, shops, casino and the beach.... not too far from all the great restaurants...
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    Location Information
    Simpson Bay, Sint Maarten SXM
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Hot Tub
    • Wi-Fi
    • 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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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Washer
    • Satellite TV
    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Sauna
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    “The Reef “ is a beautiful 5 bedroom contemporary villa, superbly positioned on the Simpson Bay Lagoon on the Dutch side of the island of St. Martin/St. Maarten. The villa has its own private boat dock, an amazing lounging terrace with very private exterior living areas and a beautiful waterfront,...
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    Simpson Bay, Sint Maarten
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Summer Hill is a free standing private villa perched on top of one of the hills of Pelican Key, Dutch St. Maarten. The villa boasts 200 degree views of the turquoise waters of the Caribbean Sea and on a very clear day you can see the neighboring islands of Saba, Statia, St. Kitts and Nevis. This...
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    Simpson Bay, Sint Maarten
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Provence at Pelican Key, Saint Maarten - Ocean View, Pool, Lovely Outdoor1 / 39
    (1)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • DVD Player
    • Internet Access
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 28, 2015
    The excellent location in terms the security of Pelican Key, the views of this unit and its large size to accommodate large groups as ours made this a good choice.Even though...
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    About this property
    Provence is a beautiful 6 bedroom, 4.5 bathroom villa with gorgeous views located in Pelican Key. This villa features a well-equipped kitchen, dining area, air-conditioned bedrooms - 5 bedrooms have king size beds and the 6th has 2 twin beds, 3 ensuite bathrooms, 1.5 shared bathrooms, a pool and...
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    Simpson Bay, Sint Maarten
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Ocean front 30 feet from the stunning blue Ocean1 / 23
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Mountain Views
    • Wi-Fi
    • DVD Player
    • Washer
    • Waterfront
    • Satellite TV
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 18, 2015
    This villa is literally perched on the edge of the ocean. Two large bdms with spacious baths, large kitchen and living area. Balcony overlooks ocean and there is a private...
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    About this property
    This unique oceanfront getaway close to the all the action that makes St. Martin/Sint Maarten so famous,will transport your mind and spirit to peaceful and memorable holidays. Ocean shore condo sleeps four in two bedrooms. This two bedroom, two bathroom condo combines breathtaking view of the...
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    Simpson Bay, Sint Maarten 007
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Villa Balaclava - Luxury villa " MAGNIFIQUE"1 / 48
    (2)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Ocean Views
    • Waterfront
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 22, 2016
    This beautiful Villa is close to all of the places that we like to go, You are close to the bars and restauraunts in Simpson's Bay, The airport and Maho are a short drive. The...
    Reviewed January 17, 2016
    What a great place Michael was amazing We had a small problem we called Michael and he was shortly and had it fixed and followed to make sure everything was working well
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    About this property
    A modern tropical retreat in an enclave of privacy offering breathtaking views over the Caribbean sea. Located a few minutes drive away from: - Hollywood Casino - Buccaneer Beach Bar BBQ - Supermarket - French Bakery serving breakfast all day and lunch, Take a stroll on the beach, shopping...
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    Simpson Bay, Sint Maarten 00000
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Waterfront
    • Internet Access
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Faja Lobie has become a very popular rental home over the last two years. This beautiful, newly renovated three bedroom, three bath villa sits directly on Bourgeaux Bay beach in the residential area of Beacon Hill on the Dutch side. This home offers a wonderful combination of indoor and outdoor...
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    Simpson Bay, Sint Maarten 78866
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    AQUALINA 102...Face the gorgeous Caribbean Sea along one of St. Maartens1 / 19
    (4)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    • Satellite TV
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Love the condo. Right on Simpson Beach, within walking distance to restaurants and bars. Kitchen is great if you choose to cook, all the kitchen items you need. We choose to...
    Reviewed March 1, 2016
    10 days of paradise and bliss.Unit is on main floor steps from the beach and ocean.Sunsets were amazing each night.Hot tub on deck and BBQ were great!Underground...
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    About this property
    Rates vary depending on # of bedrooms rented. Please see rate table or call for details.Crystal clear turquoise sea flecked with dazzling tropical sun, powdery white sands stretching along one of St Maartens longest beaches; Lush exotic foliage surrounding an elegant building of architectural...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    • Satellite TV
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Place Villa at La Siesta Residence is an oceanfront, 2nd floor, 2 bedroom condo (both with king beds and ensuites) located directly on Simpson Bay beach with an oceanfront pool. Sea Place is on the Dutch side of St. Maarten/SXM in a quiet residential neighborhood conveniently located to...
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    Simpson Bay, Sint Maarten SXM
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Caribbean Sun1 / 33
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Waterfront
    • Washer
    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 31, 2016
    The entire property is very well maintained (pool and grounds were great, nice beach), and our condo had everything we needed. Terrific grocery shopping literally five minutes...
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    About this property
    This is a great property if you if you like low key with a fantastic view. Being in the middle of Simpson Bay you can walk a mile in either direction. The property has a great pool and the beach in front is never crowded. The owner has outfitted the unit with most everything to make your stay very...
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    Simpson Bay, Sint Maarten SAINT MARTIN
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Waterfront
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled on the beautiful beach of Burgeaux Bay in the area of Beacon Hill in Dutch St. Maarten, Villa Sunshine is a wonderfully spacious 6 bedroom, 6 bathroom home offering beautiful views over the ocean. The villa is constructed on one level providing easy access and movement and has a vibrant...
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    Simpson Bay, Sint Maarten
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • Washer
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Caribbean Summer Promotion!Booking window Aug 1 till Aug 31 2017Travel Window Aug 1 till Dec 14 2017 (Thanksgiving week excluded)5-6 nights stay additional 10% discount on the best available rate7 nights stay additional 15% discount on the best available rate Valid on all NEW BOOKINGS ONLY every...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Patio
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • DVD Player
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Air Conditioning
    • Patio
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    They say a picture is worth a thousand words… That being said, Witenblauw speaks volumes when it comes to making memories of a lifetime. This ocean side paradise redefines the traditional get-a-way vacation experience. This is a true escape from reality into a living fantasy. To experience...
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    Simpson Bay, Sint Maarten
    Rental Home - 6 Bedrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Parking
    • Washer
    • Satellite TV
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Caribbean Sea and Dutch St. Maarten's spectacular sunsets. Each of...
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    Location Information
    Simpson Bay, Sint Maarten
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Waterfront
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Washer
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7th Night Free! Apr 15 - Dec 15, 2017Restrictions Apply!St Tropez sits high up on the hill in Pelican Key in Dutch St Maarten and offers outstanding views of the Caribbean Sea and glorious sunsets. This St. Maarten vacation villa for Heineken Regatta participants or fans. St Tropez is comfortably...
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    Simpson Bay, Sint Maarten
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    WOW WOW WOW, STUNNING INSIDE AND OUT! VILLA LIBRE`1 / 65
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Waterfront
    • Washer
    • DVD Player
    • Patio
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 6, 2016
    My wife and I stayed there for 8 nights. From the moment the front door was opened I was in love with the condo, the view, and the amenities. The sounds of the waves throughout...
    Reviewed April 12, 2016
    We stayed in the house for a week and we loved it! Best view of the island, no wonder why we never went out for dinner! The sunsets, the sound of the waves, the private pool...
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    About this property
    BEST VALUE IN ST.MAARTEN! Oceanfront villa with private pool on deck with 240* ocean view. 3 bedrooms with own bathrooms. The entire 2100 sqft has been recently renovated. While the villa is located in a secure gated community of 16 villas, it is extreamly private. Close to beaches, shops,...
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    Simpson Bay, Sint Maarten 000
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Villa Laluna1 / 24
    (1)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa LaLuna is one of the few homes on this wonderful island of Sint Maarten that is located on the beach. The inviting home has 4 of its 5 bedrooms that give you spectacular ocean views. The villa is also in a great location because you are within walking distance to great entertainment ,...
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    Location Information
    Simpson Bay, Sint Maarten 97150
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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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)
    • Satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 pool or under the shaded wraparound veranda.... What a lovely way to spend...
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    Simpson Bay, Sint Maarten
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Satellite TV
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    built on rocks overlooking the ocean this villa will seduce you by its uniq charm. In-between two seas you will have the amazing sunrises on Simpson Bay and sunsets on Maho Beach with the quiet sound of the waves. The ocean breeze will give you a continuous freshness. The renovated villa can...
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    Location Information
    Simpson Bay, Sint Maarten 0000
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Simpson Bay Yacht Club Condo - Unit 61 / 18
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Reviewed January 17, 2017
    This is our 2nd time staying in Unit 6. We love the location, so close to a lot of good food and fun. Having a parking spot is a major plus, the pool area is nice and always...
    Reviewed February 8, 2015
    Very nice condo and better location. Clean with two nice bedrooms. Nice balcony and shared pool. Sam did great job with any question and the secure grounds are a nice feel good...
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    About this property
    WELCOME to Simpson Bay Yacht Club, our vacation home on beautiful St. Maarten island. Is this the right property for you? We understand that choosing the "right" rental can be difficult and overwhelming. Here are some reasons why we enjoy staying in our unit. Location - Location - Location! Our...
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    Simpson Bay, Sint Maarten SXM
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    RENDEZVOUS... at Las Arenas.., a fabulous 2 BR contemporary 2 BR condo unit  on1 / 14
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Waterfront
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Wi-Fi
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 20, 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...
    Reviewed April 18, 2012
    Really it is difficult to say enough about the apartment! Upon arrival we were met by Lenka, who was extremely helpful and professional in getting us set up and explaining the...
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    About this property
    7th Night Free! May 1 - Oct 31, 2017 Maid Service offered 2x p/week when booking the 7th Night Free Promo RatesRates may vary depending on # of bedrooms rented. Please see rate table or call for details.Rendezvous, from the moment you set foot inside the luxurious St. Maarten vacation rental, gated...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Traveler-friendly cancellation policy
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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 SX
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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