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Simpson Bay Villas

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    Travellers to Simpson Bay are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    23 Matching Rentals in Simpson BayView all 90 rentals
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    Carisma on the beach1 / 22
    (30)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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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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    Barefoot Oceanfront Condo St Maarten1 / 32
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 February 2019
    My husband and I along with another couple stayed at this beautiful condo. The condo is kept beautifully, very neat and clean. Has everything you need from beach towels...grill...
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    About this property
    Barefoot is an intimate, beachfront condo located on the water's edge of Simpson Bay Beach! This is a new, beautifully decorated 2 bedroom, 2.5 bath villa located directly on Simpson Bay Beach at Palm Beach Condos - a new intimate and well designed gated community of only twenty-four units, all...
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    Simpson Bay, Sint Maarten SX
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The property is located in the very in demand location called Beacon Hill. This property has 5 bedrooms and 5 bathrooms. The villas features huge dining and living room area. The property is fully equipped with wifi , BBQ grill for great outdoor moments. It also has cable Tv, washer and dryer and...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    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 6 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 12 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
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    CARIBBEAN BLUE... 5BR beachfront home in Pelican Key1 / 46
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Caribbean Blue!! If you’re looking for a large affordable beachfront villa for a group of couples or a family reunion, you’ve found it! Located in one of St Maarten’s most popular areas, the charming community of Pelican Key, and just southeast of beautiful Simpson Bay beach, guests...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Parking
    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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. Please...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Balcony
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Carib, a new spacious 2 bedroom, 2 bath beachfront Villa of 1700 sq. ft. is located directly on one of the most beautiful (2 1/2 mile ) beaches found anywhere in the Caribbean. Often referred to as the “best kept secret” on the island, Simpson Bay Beach is truly a “jewel” amongst St. Maarten’s...
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    Location Information
    Simpson Bay, Sint Maarten N A
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Location Information
    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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
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    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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    Amenities & Details
    • 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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    Location Information
    Simpson Bay, Sint Maarten 99999
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    SMART VILLA...Beachfront at Pelican Key1 / 29
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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
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    WITENBLAUW... Magical Beach Front Estate on Pelican Key1 / 61
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • 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
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
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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
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 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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    Location Information
    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You have discovered a place where piercing turquoise waters meet the deeper blue of the sky. The pool and deck area has a private direct access to Cupecoy Beach. This is a small clothing optional beach allowing swimming in the clear blue waters. Bahia Villa is located within an easy reach of the...
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    Location Information
    Simpson Bay, Sint Maarten 0000
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Parking
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    10% Discount! April 1 - August 12, 2019. 7 Night Minimum... 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, yet is nestled at the quiet end of...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    Location Information
    Simpson Bay, Sint Maarten 00000
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Air Conditioning
    • Washer
    • Grill
    • Cable/satellite TV
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    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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    Location Information
    Simpson Bay, Sint Maarten 000
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • 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
    *SPECIAL* STAY FOR 7 PAY for 6! (4 Bedrooms +) APPLIES FOR MAY JUNE JULY AUG SEPT OCT, 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...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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