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    Travellers to Simpson Bay are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    25 Matching Rentals in Simpson BayView all 92 rentals
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    Carisma on the beach1 / 41
    (34)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Parking
    • Waterfront
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay 7 Nights & Pay For 5! Apr 14 - Dec 16, 2019 New Bookings Only. Promo cannot be combined... Beau Rivage is a comfortable, relaxing, fully air-conditioned beachfront villa is conveniently located in Beacon Hill within 5 minutes to St Maarten’s bustling Maho, the “nightlife” area of the island,...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The property is located in the very in demand location called Beacon Hill. This property has 5 bedrooms and 5 bathrooms. The villas features huge dining and living room area. The property is fully equipped with wifi , BBQ grill for great outdoor moments. It also has cable Tv, washer and dryer and...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    CARIBBEAN BLUE... 5BR beachfront home in Pelican Key1 / 46
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • DVD Player
    • Hot Tub
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7th Night Free! May 1 - Oct 31, 2019Welcome to Caribbean Blue!! If you’re looking for a large affordable beachfront villa for a group of couples or a family reunion, you’ve found it! Located in one of St Maarten’s most popular areas, the charming community of Pelican Key, and just southeast of...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Washer
    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7th Night Free! May 1 - Oct 31, 2019Sapphire 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....
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Housekeeping Included
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Poised along the cliffs at Pelican Key, overlooking the Caribbean Sea, VILLA VELAIRE welcomes you to a refined, oceanfront oasis. VILLA VELAIRE is a private two* bedroom/2.5 bath with private pool. *Rent as a 1 or 2 Bedroom, depending on your needs - if you only need 1 BR, the 2nd BR is closed...
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    Simpson Bay, Sint Maarten 00000
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    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
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 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 13 April 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    • Hot Tub
    • Washer
    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. Please inquire about lower rates offered for less than full occupancy. La Casita is an exceptional 3 bedroom, 3...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built on 3 levels, the villa’s immaculate interior spaces include a ground floor, well-equipped and welcoming kitchen, a spacious dining area with a long table easily able to seat 10/12 people and an impressive home cinema with seating for 8. The 2nd floor houses 3 large bedroom suites with king...
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    Simpson Bay, Sint Maarten 00000
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Patio
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Bisou du Soleil is a lovely, very spacious St. Maarten vacation villa rental, located high on the hillside at Pelican Key, with an unobstructed view of the Caribbean Sea from every room. Please inquire about lower rates offered for less than full occupancy.Each room opens to the patio which...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    SOL Y MAR... fabulous beachfront penthouse on Kimsha Beach! Private pool, Walk t1 / 30
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 February 2019
    Location is the best on island. Beautiful, well appointed, close to absolutely everything. Beautiful views, secure, cleaned twice during out stay. Everything was right there. No...
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    About this property
    So you want to be smak dab in the middle of the fun?!? Welcome to Sol Y Mar!! This beautiful, very unique to the island villa, offers a wonderful tropical hideaway right where St Maarten's Kimsha Beach, Pelican Key, and Simpson Bay all come together! The trifecta of fun! Click for Video. Lower...
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    Simpson Bay, Sint Maarten 99999
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Ocean Front with Private Pool1 / 17
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 May 2019
    First of all the good:The photos are exactly what you get. Many times the photos are 10 years old. Doug and his assistant/maid will respond to your every need within minutes of...
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    About this property
    Our Villa is located in Pelican Cove, a private gated community in Pelican Key located in the Simpson Bay area. This private villa is located directly on the water, has two bedrooms and an open living concept. Additionally, it has a large patio with a completely private pool. You can enjoy the...
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    Simpson Bay, Sint Maarten COLE BAY
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sol Y Mar, a charming second-level private penthouse villa, nestled between a vibrant collection of favorite eateries, bars, branch style bakeries and the lapping turquoise waters of Simpson Bay – the heartbeat of the Dutch side. As the saying goes, “location, location, location” and Sol Y Mar...
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    Simpson Bay, Sint Maarten 00000
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    SMART VILLA...Beachfront at Pelican Key1 / 29
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2015
    This condo was perfect. There were 3 huge bedrooms, a sizable living room area and 4 baths! The deck was perfect for relaxing and a few short steps down to the gorgeous beach...
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    About this property
    Villa Smart is nestled beachfront at Pelican Key and offers a totally tropical, affordable family St. Maarten vacation rental with direct beach access and glorious ocean views, does not have a swimming pool. Please inquire about lower rates offered for less than full occupancy.The terrace, full of...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    WITENBLAUW... Magical Beach Front Estate on Pelican Key1 / 61
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 October 2015
    Well worth the money!! Not only was the estate exactly as pictured, the housekeeping and grounds staff was terrific as well. We will definitely be returning.....
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    About this property
    Witenblauw Estate is a magnificent, sprawling 6 bedroom paradise built for entertaining and relaxation! If a picture is worth a thousand words then Witenblauw speaks volumes when it comes to making memories of a lifetime. This ocean side retreat redefines the traditional get-a-way vacation...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful beachfront 5 bedroom, is located in the quiet area of Beacon Hill overlooking Burgaux Bay. Sunset 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 wihch is one of the most popular tourist...
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    Simpson Bay, Sint Maarten 00000
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Air Conditioning
    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7th Night Free! May 1 - Oct 31, 2019 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...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    Villa Velaire, Oceanfront Villa with Private Pool1 / 32
    (7)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    • Washer
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 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 19 April 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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Villa Laluna1 / 24
    (2)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    Reviewed 29 July 2017
    The family of eight had a great time at Laluna villa. Private pool, on the beach, five minutes from the airport and walking distance to popular restaurants. Home does need some...
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    About this property
    Villa LaLuna is one of the few homes on this wonderful island of Sint Maarten that is located on the beach. The inviting home has 4 of its 5 bedrooms that give you spectacular ocean views. The villa is also in a great location because you are within walking distance to great entertainment ,...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Waterfront
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEW BOOKINGS ONLY - 20% Discount for 7+ nights for travel Jan 6 - Apr 14, 2019And Every 5th Night Free for travel Apr 15 - Dec 14, 2019 !!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...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Speranza, this three bedroom contemporary villa is located on a hillside facing the Simpson Bay lagoon, and the Dutch side of St. Maarten, with captivating views both day and night.   Spend your days poolside on the outside terrace that extends the width of the villa featuring an oversized...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Parking
    • Washer
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Available to be rented as a 2, 3 or a 5 bedroom villa!Found on the Dutch side of St Martin, Villa Amaryllis is a stunning waterfront located on the Simpson Bay lagoon. Amaryllis is a luxurious fully air-conditioned, 5 bedroom residence, with its own boat dock and private pool overlooking the...
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    Simpson Bay, Sint Maarten 97133
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Ocean Views
    • Housekeeping Included
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 February 2016
    I have stayed here 3 times and I am going back in Oct 2016 for TWO weeks! I am so thrilled w/this resort and rooms to stay in. The food is awesome and reasonably priced. The...
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    About this property
    Your home away from home on the Caribbean island of St. Maarten, is ideally positioned on the beach, midway between the island's most popular night spots and shopping. Fine Restaurants abound to tempt your pallet and an Activity Center makes it convenient for excursions to dive/snorkel spots along...
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    Location Information
    Simpson Bay, Sint Maarten 00000
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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