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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 209 Rentals in Simpson Bay
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    Blue Pelican Luxury Villas - Featured on HGTV!!!!!1 / 12
    (28)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Le Papillon - Modern Beachfront Unit, stunning view, great amenities1 / 24
    (4)Excellent
    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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    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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    Carisma on the beach1 / 22
    (13)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • Housekeeping Included
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 27, 2017
    My wife and I stayed at Carisma to celebrate our 10 year wedding anniversary. The villa was absolutely amazing. Paul and Carmen could not have been better hosts and the villa is...
    Reviewed June 17, 2017
    We stayed here in Jan/Feb this year and thoroughly enjoyed the experience. Paul and his wife were the perfect hosts even providing nibbles and drinks on arrival. They were...
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    About this property
    An instant feeling of genuine coziness and warmth overcomes you upon entering Charisma. Tucked away she is, in a little maze of precious ocean front properties in the peaceful Pelican Key area. Overlooking the spectacular aquatic azure Caribbean Sea, this friendly two bedroom condo, truly will...
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    Simpson Bay, Sint Maarten 00000
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW1 / 12
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Satellite TV
    • DVD Player
    • Ocean Views
    • Patio
    • Wi-Fi
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    Lovely hostess - Eve Marie!!! We were greeted with two cold Heineken and a bottle of wine in the refrigerator. Thank you! Our rental was a studio. My husband and I had a short 5...
    Reviewed 1 week ago
    My husband and I spent a wonderful 5 days vacation at Francois and Eve Marie's studio apartment in Pelican Key, St Maarten. Thank you Eve for the ice cold Heineken beers and...
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    About this property
    Spacious studio apartment with breathtaking views for rent. Located on the island of St. Maarten in the heart of the Caribbean, this fully equipped studio, located a few minutes from all amenities is your perfect tropical getaway.Enjoy our beautiful island at its best and relax at the end of a full...
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    Simpson Bay, Sint Maarten 99999
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    El Zafiro: Aquamarine Suite- Breathtaking views!1 / 22
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Terrace
    • Satellite TV
    • Wi-Fi
    • Patio
    • Secure Parking
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    El Zafiro is simply an amazing place to stay. We rented the aquamarine suite. The room was very clean and nice and the beach is directly outside of the room. Maho Bay is a...
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    About this property
    El Zafiro will lay world class luxury at your feet, your choice of a suite guarantees you an unforgettable experience the moment you walk through the gates. The lavish interior and beautiful sandy beach will transport you to another world and melt away your cares and stress. The Aquamarine suite...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    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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    Amenities & Details
    • 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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    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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    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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    Amenities & Details
    • 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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    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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Villa Balaclava - Luxury villa " MAGNIFIQUE & Full Privacy "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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    Pelican Key 1Bedroom For Rent1 / 8
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Internet Access
    • 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 queen size sleeper sofa and a bedroom with a queen bed, comfortably...
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    Simpson Bay, Sint Maarten 00090
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Caribbean Sun1 / 33
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Ocean Views
    • Waterfront
    • Satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Mountain Views
    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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    2 BEDR townhouse overlooking OCEAN  ST- MAARTEN1 / 20
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    Simpson Bay, Sint Maarten 000000
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located a mile away from the airport, El Zafiro flawlessly blends St Maarten style with fabled glamour. As with every guest in an El Zafiro suite, you are our VIP guest and the turquoise suite will remind you of this every day. With adornments of green and blue, delicate fabric and contemporary...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    La Casita Villa is the perfect destination if you are looking for a romantic getaway or an unforgettable vacation with family or friends. This vacation home is ideal for 2 to 6 people. La Casita is an exceptional 3 bedroom, 3 bathroom private home located on the oceanfront. This villa is...
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    Simpson Bay, Sint Maarten 97700
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Balcony
    • Housekeeping Included
    • DVD Player
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful brand new residence was built atop the cliffs in Beacon Hill overlooking Simpson Bay and only a few steps to the beach ; The condo has everything from contemporary design to high end bedding and a spacious gourmet kitchen one would want for a luxury tropical vacation. A short 2...
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    Simpson Bay, Sint Maarten 1744
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Washer
    • Satellite TV
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5 Bedroom Villa can be rented as a 2 or 3 Bedroom Villa at special rates! In a stunning waterfront location on the Simpson Bay lagoon, Villa Amaryllis is a luxurious fully air-conditioned, 5 bedroom residence, with its own boat dock and private pool overlooking the lagoon and the French...
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    Simpson Bay, Sint Maarten
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Washer
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    "At Seaside" is our dream...make it yours too! Serene Caribbean views can be enjoyed from the terrace. She is one of 20 units in a gated community surrounding a pool with views of the Caribbean. The grounds are lush and well tended. There is a king-sized bed and master bath off the bedroom. There...
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    Location Information
    Simpson Bay, Sint Maarten 000
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • 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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    Location Information
    Simpson Bay, Sint Maarten
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Location Information
    Simpson Bay, Sint Maarten 78866
    Rental Home - 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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    Location Information
    Simpson Bay, Sint Maarten 78866
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 6 Bathrooms, Sleeps 2 Quick View
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    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Caribbean Blue is a beach front villa in Pelican Key. With five bedrooms and five and an half bathrooms, it is a perfect house for a family vacation. Caribbean Blue may be rented with use of either 3, 4 or 5 bedrooms. The deck with a private pool at Caribbean Blue is the perfect spot for...
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    Location Information
    Simpson Bay, Sint Maarten 97700
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 2
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
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    About this property
    round floor, 1 bedroom, 2 bath apartment professionally and tastefully decorated throughout. Ceiling windows, bathrooms with deep-soak Jacuzzi tubs and rain shower heads, both bathrooms have granite counter- tops with European style vanities, expansive living room with views of Maho Bay and the...
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    Location Information
    Simpson Bay, Sint Maarten 97000
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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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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    Location Information
    Simpson Bay, Sint Maarten NA
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
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    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
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Ocean Views
    • Balcony
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    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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    Simpson Bay, Sint Maarten SXM
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Satellite TV
    • Private Outdoor Pool (Unheated)
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    • Wi-Fi
    • Hot Tub
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rates may vary depending on # of bedrooms rented. Please see rate table or call for details.VILLA BELLA VITA – Where the amenities of a Five-Star Resort luxury meet with the serenity, the privacy and the personalized service that each guest deserves.Named for the “Beautiful Life” it represents,...
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    Simpson Bay, Sint Maarten
    Rental Home - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Balcony
    • Air Conditioning
    • Internet Access
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Simpson Bay, Sint Maarten
    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
    • 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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    Simpson Bay, Sint Maarten 9999 XX
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Caribbean Blue at Pelican Key, Saint Maarten - Beachfront, Amazing Sunset View1 / 43
    (5)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Satellite TV
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    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 20, 2017
    This is a lovely villa, the setting could not be more perfect. The patio faces south-southwest, just enough so you have great sun all day and beautiful sunsets at cocktail hour...
    Reviewed October 12, 2016
    My family of 8, two daughters & a son and there spouses, and my husband and I stayed here for 10 days starting on Boxing Day. We cannot say enough about this beautiful...
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    About this property
    Caribbean Blue is a beachfront villa in Pelican Key. With five bedrooms and five and a half bathrooms, it is a perfect house for a family vacation! The deck at Caribbean Blue is the perfect spot for enjoying the sun and sea, and has wonderful views of the island of Saba, and of the sunset. Pelican...
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    Simpson Bay, Sint Maarten 78866
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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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
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    • Shared Outdoor Pool (Unheated)
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    • 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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    Location Information
    Simpson Bay, Sint Maarten 97150
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located right on the beach in prestigious Pelican Key area on the Dutch side of St. Maarten lays IL Punto Blu. Convenience, spaciousness and panoramic views are the distinct advantages along with outstanding amenities at IL Punto Blu. Does the thought of crowded hotels and time-share sound...
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    Simpson Bay, Sint Maarten 97700
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    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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    • Patio
    • DVD Player
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    • Private Outdoor Pool (Unheated)
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    VILLA VISTA – The name says it all!! This magnificent 5 bedroom 6 bath luxury Villa features stunning panoramic views from virtually every room and every angle! Villa Vista features 3 large suites on the main floor in addition to 2 private studio suites on the lower level with both studios...
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    Simpson Bay, Sint Maarten 97700
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Hot Tub
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located over the hill on the sea at Pelican Key, Daffodil is a luxurious,5 bedrooms, 5 bath villa, whose unique glistening cerulean blue tile roof promises a memorable vacation experience. It’s Dutch flavor is showcased by colorful furnishings from international designers, and represents the...
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    Simpson Bay, Sint Maarten 78866
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 8
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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
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    • 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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    Simpson Bay, Sint Maarten ST MAARTEEN DWI
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 colours in the morning and unique sunsets. The villa is located within walking distance to great restaurants...
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    Simpson Bay, Sint Maarten 97700
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    7 Bedrooms, 9 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Unheated)
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    VILLA BELLA VITA – Where the amenities of a Five-Star Resort luxury meet with the serenity, the privacy and the personalized service that each guest deserves. Named for the “Beautiful Life” it represents, Villa Bella Vita was once proclaimed as one of the Leading Estates of the World. This...
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    Location Information
    Simpson Bay, Sint Maarten 97700
    Rental Home - 7 Bedrooms, 9 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Patio
    • Satellite TV
    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 97700
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Aqualina 102 - Ideal for Couples and Families, Beautiful Pool and Beach1 / 15
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 7, 2016
    Just stayed a Aqualina for 6 amazing night that never dissappointed us! The views are incredible-steps to the beautiful turquoise sea. Condo was gated with security and nicely...
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    About this property
    Crystal clear turquoise sea flecked with dazzling tropical sun, powdery white sands stretching along one of St. Maarten’s longest beaches; Lush exotic foliage surrounding an elegant building of architectural beauty. All of this belongs to Aqualina, St. Maarten’s newest luxury beach front...
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    Simpson Bay, Sint Maarten 97700
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Faja Lobie1 / 32
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Faja Lobie has become a very popular rental home. This beautiful, three bedroom, three bath villa sits directly on Bourgeaux Bay beach in the residential area of Beacon Hill on the Dutch side of St. Maarten. This home offers a wonderful combination of indoor and outdoor living space. The interior...
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    Simpson Bay, Sint Maarten 11111
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Parking
    • Wi-Fi
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 at Palm Beach Condos, a intimate well designed community of only 24...
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    Simpson Bay, Sint Maarten
    Condo/Apartment - 3 Bedrooms, 3 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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    • Terrace
    • Satellite TV
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Coco Beach Duplex1 / 21
    (3)Average
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 11, 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 September 6, 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 can...
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    Location Information
    Simpson Bay, Sint Maarten 11111
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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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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    Location Information
    Simpson Bay, Sint Maarten 007
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Satellite TV
    • DVD Player
    • Hot Tub
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Aqualina 102 St Maarten. Families or groups of four often find it difficult to locate luxury accommodations with the same long lists of amenities that larger villa properties offer. However, Villa Aqualina Beach Club Unit 102 has been created with such groups in mind. With two bedrooms and 2.5...
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    Location Information
    Simpson Bay, Sint Maarten
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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