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Holiday Rentals with Pools in Sint Maarten

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    Travellers to Sint Maarten are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    267 Matching Rentals in Sint MaartenView all 495 rentals
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    Blue Pelican Luxury Villas - Featured on HGTV!!!!!1 / 12
    (29)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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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    DUE TO HURRICANES, NO AUTO-BOOKS OR BOOKING REQUESTS FOR STAYS BEFORE MID. 20181 / 93
    (5)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Beautiful beachfront at The Villas On Great Bay1 / 44
    (18)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 October 2015
    This property is in a great location to downtown area in Phillipsburg. Walk to town and restaurants. Right on the beach! Quiet and clean! Jim, the property Manager was...
    Reviewed 1 July 2015
    This comfy condo was perfect for us...spacious, excellent location, well kept and supplied. Some details and things to know:Inside: comfortable and very roomy and homey...
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    About this property
    This two bedroom, two and a half bath villa is situated right on Great Bay Beach in a small complex of twelve individual villas with a lovely beach front swimming pool and breath-taking ocean views. This gated complex with on-site management is the perfect place to relax around the pool or to just...
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    Philipsburg, Sint Maarten 97100
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 6
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    Carisma on the beach1 / 22
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Housekeeping Included
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 August 2017
    Thank you Paul and Carmen! Villa Carisma was the perfect choice for our family; such a beautiful beach front property.Our experience: We wanted a beach front property with...
    Reviewed 27 June 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...
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Flamboyant: 2BR - Amazing view, right on the shore1 / 12
    (8)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Housekeeping Included
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 June 2015
    Dislikes:-ac only in bedrooms, so the living room can become quite warm without one of the bedrooms with the ac on open.-no toilet paper until the second day. Flying for 14...
    Reviewed 15 April 2015
    Warm welcome by the team ! After several hours on plane, we were happy to see how incredible was the sea view ! and it was ours for some days :)The house was clean, wifi and...
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    About this property
    Located 8 km from Orient Bay Beach, the Villa Flmaboyant offers a terrace and an outdoor swimming pool. Our accommodation features free Wi-Fi. This property offers TV, air conditioning and a fully equiped kitchen including a microwave, a refrigerator, a freezer and many other equipments. Private...
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    Oyster Pond, Sint Maarten 97150
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Loue suite de luxe 6/8 personnes(DBC Westin)1 / 36
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2017
    we had a terrific experience renting this unit from Francois. no issues with payment, check-in was simple and attending any time share sales efforts were voluntary.the access...
    Reviewed 15 March 2016
    This was a beautiful spacious condo with a spectacular view over Dawn Beach and high enough to see over to Oyster Pond. Lots of room, very spacious rooms Possibly the most...
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    Oyster Pond, Sint Maarten WESTIN HOTEL
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cupecoy Beach Club Unit 208 Deluxe Hotel Room1 / 13
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 December 2016
    We loved this property! Beautiful interior furnishings, spacious studio unit and large balcony with full water view. Many boats pass by but far enough away from the airport...
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    About this property
    Cupecoy Beach Club unit 208 second floor deluxe oceanfront hotel room with private oceanfront balcony including daily maid service.. Located within step to complex large freshwater pool with swim up bar. Complex is a gated community with 24 hour security. Resort is located across from...
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    Cupecoy Bay, Sint Maarten NONE
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    ISLAND DREAMS!1 / 24
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Ocean Views
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Waterfront
    • Housekeeping Included
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 January 2017
    This villa was even better than advertised. It is spacious and tastefully furnished in the tropical island pastels and style and had everything we needed, even down to paper...
    Reviewed 5 March 2016
    We visited all parts of the island and many beaches. All were very nice. Our favorite place was Pinel Island as we really like to snorkel. I wish we would have planned more...
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    About this property
    'ISLAND DREAMS,' ~~ Coral Shores Villa #2 has a 45 foot deck overlooking the turquoise Caribbean sea with beautiful sunsets, lots of sunshine and soft Caribbean breezes. Nothing in front of you to mar the wrap around view. Swim in the large pool or the sea. Imagine sunshine filled peaceful days...
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    Sint Maarten, St Martin / St Maarten DWI
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Westin Dawn Beach Club St. Maarten1 / 8
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 May 2017
    Beautiful 3 bedroom condo with a view of the ocean. Perfect for our family vacation. Plenty of room for everyone to gather as well as have some personal space. Kitchen was...
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    About this property
    Weekly rental (Saturday to Saturday) available from April 9th through December 17th. Three-bedroom, luxuriously appointed, condo with quality furnishings, granite countertops, and indulgent baths. While relaxing in your own residence, you can enjoy all that Dawn Beach has to offer. The condo is...
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    Oyster Pond, Sint Maarten SM
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2BR-Oceanfront-Royal Palm1 / 10
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Ocean Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 May 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 15 February 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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    Villa Angelina Amazing Panoramic Views Undamaged by Hurricane1 / 24
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 February 2017
    We wanted a special place to celebrate our fortieth anniversary. After much research (you'd have to know my husband) we settled on Villa Angelina and know we could not have done...
    Reviewed 29 May 2016
    We loved our stay at the Villa Angelina! The view is just breathtaking..... The location is perfect , very private , total tranquility and serenity! We can't wait to come back...
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    About this property
    If you are looking for relaxation and tranquility than Villa Angelina villa is the perfect villa for you and your family or friends. The villa can accommodate up to 6 people. Villa Angelina is situated on the Oyster Pond hillside with amazing views of the Atlantic Ocean, St. Barth’s, Relax and...
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    Oyster Pond, Sint Maarten 00000
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Studio in Pelican Key Paradise1 / 11
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 June 2014
    We stayed in Jackies Appartement for 10 days. The Appartement is new renovated and has a nice littel Balkony surrounded by palm trees. It has a brand new shower with different...
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    About this property
    Newly renovated studio features a kitchenette with full fridge, 4 burner glass stove top, microwave, toaster oven, and coffee maker. King size, very comfy bed, flat screen cable tv, and sofa, bathroom with multi jets including rain shower head, and a balcony with seating for 4 overlooking the...
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    Simpson Bay, Sint Maarten 00014
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    La Terrasse Maho1 / 33
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 February 2016
    First, we must acknowledge the owners - Francois and Eve-Marie. They were prompt in our initial request for rental. They sent us an email, and had Royal Islander staff find us...
    Reviewed 14 January 2016
    We stayed at La Terrasse over the holidays with our two young children. It was perfect! The apartment is beautiful and completely renovated. It is very well equipped with...
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    About this property
    Located on the 2nd Floor of the La Terrasse in Maho, this fully remodeled One Bedroom Unit boasts terrific views of the Caribbean Ocean and Saba and is a plane spotter's paradise watching aircrafts land at the famous SXM Airport. This fully renovated furnished One Bedroom unit is located on the...
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    Maho, Sint Maarten 00000
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Villa Bleu Matisse: Amazing View on Ocean1 / 17
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Washer
    • Ocean Views
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 June 2017
    The deck, the unit, the ocean, the pool......lots to like. Kitchen was ok. Bathroom was very nice. Bedrooms were nice, each with walk out sliders.The only down side to the...
    Reviewed 20 April 2017
    We were looking for a clean quiet place close to the ocean. This place didn't disappoint. All is very functional and there is a nice pool to cool off. The large deck was...
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    About this property
    Villa Bleu Matisse is a 2 bedroom/2 bath villa with a large deck and a private pool. The house i overlooking the ocean on the East side of the island, offering an amazing view. the villa has a fully equipped kitchen incl. a dishwasher, Wifi Internet and Satellite TV. You can either enjoy the inside...
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    Location Information
    Oyster Pond, Sint Maarten 97150
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Wi-Fi
    • Waterfront
    • Children's Pool
    • Air Conditioning
    • Ocean Views
    • Sauna
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A lovely 3-Bedroom, 2-Bathroom apartment, easily sleeping 8 guests, 1800sq ft, perfect for families. This is a luxurious residence, steps from the famous Dawn Beach (perfect sunrises) and only 4 miles from the island's capital Philipsburg. You will have spectacular ocean views from your balcony,...
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    Philipsburg, Sint Maarten 123
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Suite Condo Westin St Martin vue sur mer1 / 32
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Children's Pool
    • Ocean Views
    • Sauna
    • Hot Tub
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 April 2015
    Beautiful resort excellent amenities near the French side. Great brunch, restaurants, pool, casino, hot tub. Close to attractions and other restaurants, Great beach, staff...
    Reviewed 8 July 2014
    We stayed at the Westin Dawn Beach Club in June 2014. The three bedroom condo was perfect for our four teenagers and 2 adults. We spent every morning and evening enjoying the...
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    Oyster Pond, Sint Maarten 97150
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lux apart in westin dawn beach club1 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Mountain Views
    • Children's Pool
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 January 2016
    I had an amazing stay, easy booking with Jacques and great property in St-Marteen. The space exceeded my expectations in every way. The service was great and among the best I...
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    About this property
    Rent 8 person in Westin Dawn Beach Ressort & spa St. Marteen. Appartment of 1800(s.foot), 3 bedroons (with 1 parental with dressing ) sofa bed in parlor, 2 bathrooms, kitchen full equip., satellite Tv in all rooms. Infinity pool, casino, restaurants, privante beach. Free parking available. Please...
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    Oyster Pond, Sint Maarten NETHERLANDS
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cool Bay Villa St Maarten1 / 21
    (16)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Grill
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 January 2016
    We rented this adorable villa with our two teenage kids for a Caribbean Christmas Vacation. The beginning of our vacation didn't start off so well. The owners were out of town...
    Reviewed 17 September 2014
    Go!! For tomorrow is later. Near there supermarket, and drugs. The Maho Beach is near in car too. Near there Dominican food, no is so expensive.
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    About this property
    Rigth next to St Maarten' s Lagoon - A lovely setting, surrounded by trees and plants. Just a short 2 miles hop to the beach, this traditional Caribbean (65m2) villa is ideal for a family. Fully air-conditionned,it has a terrace and a balcony with garden furniture, including hammock, parasol and...
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    Simpson Bay, Sint Maarten 97150
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Sugar Bird Townhouse Apartment with Ocean View1 / 48
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Mountain Views
    • Wi-Fi
    • Ocean Views
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 2017
    There is nothing like sleeping to the sound of the ocean and waking in the morning to beautiful sunrises!! When you arrive Heather has the refrigerator stocked with goodies and...
    Reviewed 3 February 2017
    Just got home from staying in this roomy apartment for 18 days. Every thing we needed was provided and Heather was great. Great neighbors and friendly neighborhood pups. The...
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    About this property
    Sugar Bird town house is your tropical home away from home nestled in a quiet corner of Pointe Blanche Bay. Perfectly suited for those interested in a longer stay, this extremely large, bright and airy one bedroom town home is well appointed with every detail right down to beach towels and birthday...
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    Location Information
    Philipsburg, Sint Maarten 00000
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Villa Oyster Pearl, Private Beach Access.1 / 39
    (52)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Housekeeping Included
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2017
    My family loved our stay at the Villa Oyster Pearl! The host is very welcoming and the home and property are a bona fide paradise. We were so glad to have chosen this as our...
    Reviewed 16 August 2017
    We were so impressed by the Villa Oyster Pearl. The house itself is spacious, comfortable, and gorgeous, from the breezy veranda with a view of St. Barth's and the...
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    About this property
    Rated as EXCELLENT by Tripadvisor. Villa Oyster Pearl is the perfect choice to ensure your vacation on the island is exquisite beyond everything you have ever dreamed. Should you choose, you will be met at the airport by our friendly host, who will guide you to the villa and cater for your needs....
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    Location Information
    Sint Maarten, St Martin / St Maarten 12345
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Spacious 1 BR Condo, Ocean Views, Maho, St Maarten1 / 20
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Sauna
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Children's Pool
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2017
    Beautiful view! The pool was never really crowded. I give it a 4 because I couldn't "hear" the waves coming to shore but you certainly have a view of the ocean.The owner...
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    About this property
    Spacious, comfortable and fully equipped, this condo allows for a pleasant stay with all the amenities. The condo is centrally located in famous Maho village. You will feel at home in this fully air conditioned apartment. From the spacious living room you can enjoy sweeping views via the floor to...
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    Location Information
    Maho, Sint Maarten SXM
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    WESTIN DAWN BEACH CLUB ST. MAARTEN 3 BEDROOM CONDO1 / 31
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Ocean Views
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2017
    The 3 bdm condo at the Westin Dawn Beach is spacious with a well-equipped kitchen. All 3 bdms have king size beds with comfortable Westin bedding. The beds are changed midweek...
    Reviewed 3 March 2017
    Honestly, the condo here is beautiful. The grounds are beautiful as well. Our view, the interior and surrounding area is gorgeous. The location is wonderful as well. It is...
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    About this property
    NO AVAILABILITY FOR 2016. AVAILABLE 2017 Newly Completed 3 LARGE bedroom Condo is within the Dawn Beach Club on Dawn Beach in St. Maarten, Dutch side (for week 7 February break, all other weeks aren't guaranteed any particular building or floor, depends on availability). February break (week 7)...
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    Location Information
    Philipsburg, Sint Maarten NA
    Condo/Apartment - 3 Bedrooms, 2 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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    Amenities & Details
    • 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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    Beautiful 3 Bedroom Ocean view Condo1 / 12
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Waterfront
    • Balcony
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 April 2015
    I was very nervous booking a property where we had not visited previously. We were very happily surprised. The host was excellent followed-up immediately to any questions and...
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    About this property
    Dawn Beach Club stretches along the shore of Dawn Beach on the island’s Dutch side. Enjoy accommodations with a large private balcony overlooking the ocean, fully equipped kitchen, three bedrooms, and spacious living areas. The adjacent Westin Dawn Beach Resort and Spa has casino gaming, concierge...
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    Philipsburg, Sint Maarten 46226
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Ocean Views
    • Cable/satellite TV
    • Sauna
    • Wi-Fi
    • Hot Tub
    • Children's Pool
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Oyster Pond, Sint Maarten 1744
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Dawn Beach Westin, Very spacious, many services1 / 28
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Hot Tub
    • Sauna
    • Internet Access
    • Washer
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 December 2014
    We thoroughly enjoyed our stay at the Westin in Dawn Beach. The hotel facilities were always clean and the staff was friendly and helpful.
    Reviewed 26 April 2014
    Wow, what a great vacation! We were worried at first as we read some of the comments, but no way, our experience was absolutely amazing! We always travel to very expensive...
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    About this property
    DUE TO HURRICANE IRMA, MY UNIT AT DAWN BEACH CLUB WON'T BE AVAILABLE, AT LEAST, UNTIL DECEMBER 2018. CONDOS WILL BE COMPLETELY REBUILT. UPDATES WILL FOLLOW ON THE NEXT MONTHS. Dawn Beach Club, Very Spacious, Ocean Front Five star private resort at the Westin Hotel & Spa in St Maarten (Version...
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    Oyster Pond, Sint Maarten 1234
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Blue Marine, Maho Spectacular Views, Best Location1 / 7
    (2)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Mountain Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 2015
    My husband and I stayed here with another couple for 5 nights and couldn't have asked for better accommodations and hosts. Just a few minutes walk from the Maho Beach...
    Reviewed 4 January 2014
    My family and just finished staying in a Blue Marine residence and although it was NOT this specific property, I know they are all similar aside from the owners. We had a great...
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    About this property
    2 bedroom 2 1/2 professionally designed modern condo in Blue Marine, located in Maho. Walk to 2 beaches, restaurants, casinos, nightclubs, grocery. Huge pool and stunning patio with view of the sea, lagoon, mountains, golf course. Secure, wheelchair accessible.
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    Maho, Sint Maarten NONE
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Tranquil Settings, Porto Cupecoy (1 or 2 br opt)1 / 34
    (6)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 February 2015
    I had the privilege of renting Cynthia’s condo in January 2015 with my husband and 21 year-old daughter. We were very pleased with our stay and highly recommend this property...
    Reviewed 17 January 2014
    The name Tranquil Setting is true to the feeling you get as you walk in. It is at once peaceful and elegant. The owner has taken great care to provide a luxurious feel in a...
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    About this property
    Welcome to Tranquil Settings at Porto Cupecoy! St Maarten, (Sint Maarten) ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Luxury Condo nested in a gated community, seconds away from Cupecoy beach: 2 Bedrooms, 2.5 Baths (Sleeps 2-4) Rates: (choose between 1 bdrm or 2bdrm...
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    Cupecoy Bay, Sint Maarten CUPECOY
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Mountain Views
    • Ocean Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect location between Simpson Bay & Philipsburg,in the new gated community of"Indigo Bay Beach". This brand new exquisite residence, very well modern decorated & equipped. Beautiful living area, lots of glass doors that open to a private pool, wrapped by a huge deck offering incredible panoramic...
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    Simpson Bay, Sint Maarten NA
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cupecoy Beach Club Oceanfront second floor two bedroom condo unit with three private bathrooms and two oceanfront balconies within guarded condo complex. This unit can be rented three different ways as a two bedroom, one bedroom or deluxe hotel room all with daily maid service. Unit overlooks...
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    Cupecoy Bay, Sint Maarten NONE
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Pelican Key 1Bedroom For Rent1 / 9
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Internet Access
    • Cable/satellite TV
    • Balcony
    • Terrace
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1 bedroom/1bath unit is located in Pelican Key/Simpson Bay' next to LaVista Resort. Within walking distance to many restaurants, bars, grocery store and casino. The unit has a full kitchen with all the comforts of home, a futon sleeper sofa and cot downstairs for 2 and a bedroom with a king...
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    Simpson Bay, Sint Maarten 00090
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Amazing Runway Villas on the lagoon1 / 26
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 February 2016
    Just got back from a two week stay at the Amazing Runway Villas on the Lagoon, Mullet Bay/Maho Beach area. What a WONDERFUL hostess and situation. Privately owned villas, gated...
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    About this property
    Two lovely Private entrance Suites in waterfront Villa in Sint Maarten . The 2 Suites have private entrance, bath, safe boxes, tv, wifi internet all over the property, BBQ, bar, pool lounge common area, property is on the lagoon with boat accessibility . 5 minutes away from airport and also...
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    Location Information
    Sint Maarten, St Martin / St Maarten XXX
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • Washer
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    • Wi-Fi
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    • Private Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located a few miles from Orient Bay Beach, Villa Seaview offers a large terrace and an outdoor swimming pool. Our accommodation features free Wi-Fi. This property offers TV, air conditioning and a fully equiped kitchen including a microwave, a refrigerator, a freezer and many other equipments....
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    Oyster Pond, Sint Maarten 97150
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Gorgeous beachfront villa1 / 23
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Ocean Views
    • Grill
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 October 2013
    Our family of 4 (one kid is 4 years old, another is 14) had fantastic one week stay at this villa. We've traveled quite a bit all over Caribbean, so, I had very clear idea of...
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    About this property
    Villa #9 on the left edge of 'VILLAS ON GREAT BAY' complex, directly on the beach of Philipsburg, the capital of dutch St.Maarten. Being the side villa it offers more privacy and tranquillity. On the ground floor: terrace on the beach with wooden floor, a lanai to enjoy meals and drinks in front...
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    Philipsburg, Sint Maarten XX
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bdrm Condo with Superlative Views of St. Barts1 / 11
    (3)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Grill
    • Mountain Views
    • Internet Access
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2016
    The apartment is beautiful and conveniently located. There is a small grocery store and restaurants nearby in Oyster Bay. The views from the apartment are gorgeous, except...
    Reviewed 29 August 2014
    My friends and i rented this one bedroom condo for the week-end and we had a blast, the staff were immediately friendly and helpful, the condo itself was really cool, we had a...
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    About this property
    'Superlative views of St. Barts' is how one renter described the view from Princess Heights unit 402. From the time you walk in through the mahogany front door, you'll know why this luxury boutique hotel with its granite counter tops, recessed lighting and marble floors, is consistently rated by...
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    Philipsburg, Sint Maarten NETHERLANDS ANT
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 5
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    Caribbean Sun1 / 33
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 December 2016
    The entire property is very well maintained (pool and grounds were great, nice beach), and our condo had everything we needed. Terrific grocery shopping literally five minutes...
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    About this property
    This is a great property if you if you like low key with a fantastic view. Being in the middle of Simpson Bay you can walk a mile in either direction. The property has a great pool and the beach in front is never crowded. The owner has outfitted the unit with most everything to make your stay very...
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    Simpson Bay, Sint Maarten SAINT MARTIN
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Survived Irma!!  Beachfront gated Condo directly on Simpson Bay1 / 16
    (4)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Waterfront
    • Grill
    • Air Conditioning
    • Washer
    • Ocean Views
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 February 2017
    We spent a week at Kelly and EJs beautiful condo at The Palms.This condo is spacious, bright and inviting. There is everything from a full kitchen, beach towels, information...
    Reviewed 7 January 2015
    We recently rented a 1 bedroom at Simpson Bay Resort. Although we were in the older building that was in need of some updating we were very pleased with the size of our room...
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    About this property
    Survived Irma!! Beautifully decorated 2 bedroom, 2.5 bath villa located directly on Simpson Bay Beach at Palm Beach Condos on the Dutch Side of St. Maarten, a new intimate and well designed gated community of only twenty-four units, all facing both the pool and the beach beyond. The layout was...
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    Simpson Bay, Sint Maarten 00000
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Sea La Vie: 4 bedr with views of the ocean and St Barths | Island Properties1 / 25
    (1)Very good
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    • Grill
    • Patio
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 January 2016
    My wife and I along with our 6yr old stayed at Sea La Vie villa for a week. We rented the home thru St. Martin Reservation Center and my contact was Ted. The home is as...
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    About this property
    Villa Sea La Vie is a wonderful, new 4 bedroom/5 bathroom villa located in the gated community of Red Pond Estates on St. Maarten. The villa offers breathtaking views of the ocean and the neighboring island of St. Barths in the distance. The villa’s two-level space, rooms, terrace area and...
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    Location Information
    Philipsburg, Sint Maarten 00000
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Housekeeping Included
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our beautiful villa Sea Dream located on the hillside in Happy Bay. It is a gorgeous villa and only a 5 minute walk from the beach at Happy Bay. Friar's Bay is also very close and has 2 beach restaurants that are very popular with guests. The villa has gorgeous views of the ocean...
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    Location Information
    Cupecoy Bay, Sint Maarten
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    THE CLIFF1 / 11
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Sauna
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 April 2017
    I will keep this view in my heart forever! I would wake every day to see the sun rise and look forward to the evening to watch it fall. The private beach is like no other. Think...
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    About this property
    The Cliff is a 5 Star Condominium in Sint Maarten. My Condo is 1,550 sq ft. It is a huge 1 bedroom 1 bath condo with a Beautiful ocean view. The Cliff is 5 years young. The Condominium is gated and also has an indoor pool, and lighted tennis court, fitness center, Dior Spa and cafe. The Cliff at...
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    Cupecoy Bay, Sint Maarten D W I
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BEACH HOUSE GIANNA is truly one of a kind. A very special place. Its location is perfect being directly on the ocean and Dawn Beach, and WITH DIRECT ACCESS to the BLUE SEA and one of the island's finest beaches. PLEASE NOTE, VILLA CAN ME RENTED AS A ONE BEDROOM AT A REDUCED RATE. WE SIMPLE LOCK...
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    Location Information
    Sint Maarten, St Martin / St Maarten SXM
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This one bedroom townhouse is in one of the most desired areas on St Maarten. Pelican Key has bars, restaurants, beaches, and a casino, all within a 10 minute walk. The unit sets on the 2nd and 3rd floor of a small condo complex, with a shared swimming poo. The unit has some nice views from the...
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    Location Information
    Simpson Bay, Sint Maarten 000NA
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Villa Vacation Dream at Indigo Bay Estates (fully intact after hurricane)1 / 31
    (6)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Washer
    • Air Conditioning
    • Waterfront
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 June 2017
    This place was absolutely amazing. I was picked up at the airport by Martin, and he made me feel very welcome. The view you have from the living room is unlike anything else. In...
    Reviewed 28 May 2017
    We (family with 3 children) had a great stay at this holiday resort. It was clean, safe, the view on the Caribbean Sea was amazing and it is a quiet place. It is also perfectly...
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    About this property
    Gorgeous Villa in Paradise nestled in the hillside of the Indigo Bay Estates only a short walk to the beach. The resort offers 24 hour gated security for optimum privacy and safety. The living and open kitchen area opens onto an outside pool area that boasts breathtaking views of the surrounding...
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    Location Information
    Cole Bay, Sint Maarten 0000
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    HGTV Beach house  -  Private Pool1 / 33
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Waterfront
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 March 2016
    We loved St. Maarten and loved our stay at the HGTV Beach House. The house is more beautiful than the pictures! Our grandkids (ages 4 and 2) were in the pool whenever we were...
    Reviewed 4 August 2015
    My family just returned from a 10 night stay at Villa Incognito, the Villa was exactly as amazing as it looks online. Incredibly well appointed, the deck furniture, and pool...
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    About this property
    Magnificent Beach Villa as Featured on HGTV International Island Getaways. Modern, \with your own private turquoise pool - located directly on the beach. Sleeps 6-8 people (4 adults and 4 kids). Discover the natural alchemy between Dutch culture and French savoir-faire in a Caribbean paradise...
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    Location Information
    Philipsburg, Sint Maarten 001
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Luxurious,modern beachview Villa1 / 37
    (1)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Indoor Pool
    • Washer
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    • Wi-Fi
    • Waterfront
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2016
    Bottom line: This is a beautiful,well-appointed, private villa with striking views of the bay. The owner has meticulously designed and built this home and you can tell a lot of...
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    About this property
    Villa Crystal is a modern villa located on Sint Maarten, in the Caribbean Islands. From the out side terrace of the villa an incredible view of St. Barth Island can be seen. Every room of the villa enters onto the terrace and faces the breath taking view. The morning sunrise brings with it...
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    Location Information
    Philipsburg, Sint Maarten 97150
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Suite 5* 3 BD 2 BA Westin Dawn Beach Sint Maarten1 / 43
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Waterfront
    • Hot Tub
    • Ocean Views
    • Children's Pool
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2016
    The layout, the view and the decor was perfect for my family of 5. My 3 teenage daughters, my wife and I really loved the convenience of easy access to the pool and beach. The...
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    Location Information
    Oyster Pond, Sint Maarten ST MAARTEN BVI
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great island! Awesome beaches. Tax free shopping. Best jewellery deals anywhere. Enjoy the wide array of dining, night clubs and casinos. Ocean club has a very nice pool accompanied by a pool side bar/ restaurant. Ocean and beach are just 100 steps away. This is on the Dutch side beside the golf...
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    Location Information
    Cupecoy Bay, Sint Maarten 00000
    Condo/Apartment - 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)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This brand new 2 bedrooms, 2 bath villa is located in Beacon Hill on the Cliffside overlooking the stunning Simpson Bay Beach. This villa has a very private pool area with mazing views on the ocean. The Front part of the property is great at night to enjoy the colorful sunsets.  The property is...
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    Location Information
    Simpson Bay, Sint Maarten 9999 XX
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Ocean Views
    • Washer
    • Patio
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SUMMER SPECIAL RENT THE ENTIRE 3BR CONDO FOR 1 LOW PRICE. $200.00 PER DAY (4 night minimum) OR $1395.00 PER WEEK Atlantica Beach Club Condos This 3 BR 2 Bath condo can accommodate all sizes of families and friends. 2 bedrooms have Queen Size beds, the other bedroom has 2 twin extra long...
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    Location Information
    Oyster Pond, Sint Maarten 00000
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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