We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Simpson Bay, St. Maarten-St. Martin

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $477 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travelers to Simpson Bay are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 12
    5 of 5 bubbles (26) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 / 10
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 / 12
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    1 / 22
    5 of 5 bubbles (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • Housekeeping...
    • Waterfront
    • Private Outdoor...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    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... View all property information
    Location Information
    Simpson Bay, Sint Maarten 00000
    5 of 5 bubbles Reviewed 4 weeks ago
    We thoroughly enjoyed your villa and all of its amenities and especially the personal care provided by both of you. It was appreciated. The decor is beautiful and provides...
    5 of 5 bubbles Reviewed October 28, 2016
    Had a wonderful time at Villa Carisma for our honeymoon. Doesn't get get much better than a private villa with jacuzzi pool right on the beach! Beautifully decorated and fully...
    See all reviews
    1 / 58
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Mountain Views
    • Air Conditioning
    • Shared Outdoor Pool...
    • Wi-Fi
    • Ocean Views
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful one bedroom condo with water views from two separate balconies. Newly renovated modern kitchen and bathroom. Relax and renew your body and mind, have fun and enjoy all the culture and activities that this beautiful island offers. Find or rediscover love. Let your dreams become a... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    5 of 5 bubbles Reviewed October 2, 2016
    Just pack your bathing suit, hat and beach shoes when booking this lovely modern quiet romantic condo for two. The owners have provided everything you need from suntan lotion...
    5 of 5 bubbles Reviewed September 27, 2016
    I am a regular and frequent visitor to SXM and have had the pleasure of staying at Bruce and Joyce's condo three times over the last couple years. This is always the first place I...
    See all reviews
    1 / 32
    4.5 of 5 bubbles (2) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Grill
    • Ocean Views
    • DVD Player
    • Balcony
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Modern 1 bedroom apartment newly built. Marble floors through out. All stainless steel appliances in kitchen and granite counter top. Hi speed WiFi internet. Dish Network Satellite TV in living room and bedroom. Air conditioning in all areas. Very private due it being a single detached apartment... View all property information
    Location Information
    Simpson Bay, Sint Maarten NA
    5 of 5 bubbles Reviewed February 8, 2014
    Apartment is private, has all new appliances, including washer and dryer and dish washer. Hot water is freely available (not always true on every island we've stayed at), little...
    4 of 5 bubbles Reviewed January 17, 2014
    This private residence is located in a quiet residential area with a wonderful host. It has everything you need and is centrally located close to a large grocery store and several...
    See all reviews
    1 / 22
    5 of 5 bubbles (7) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Waterfront
    • Satellite TV
    • Housekeeping...
    • DVD Player
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Villa Velaire can be booked as a 1 or 2 bedroom, depending on your needs, There is an additional charge of $50/per night for the 2nd Bedroom. If you need the 2nd bedroom, please email me and let me know and I will send a revised quote. PLEASE NOTE: if you only need ONE Bedroom, the 2nd bedroom... View all property information
    Location Information
    Simpson Bay, Sint Maarten 00000
    5 of 5 bubbles Reviewed August 8, 2016
    Villa Velaire was exactly as advertised. Kim was amazing to work with and made sure our stay was perfect!! My husband and I traveled with our good friends and the house was...
    5 of 5 bubbles Reviewed April 19, 2016
    My wife & I have been to St. Martin multiple times and each time have rented a different villa. Villa Velaire is by far and away the best rental we have found. The owner is very...
    See all reviews
    1 / 25
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Waterfront
    • Satellite TV
    • Ocean Views
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome in Le Papillon Penthouse, the best experience on Simpson Bay beach. - Gated, private & secure community - 3 floor penthouse - Cleaning service every second day - Roof terrace with long chairs, dining area, summer kitchen and 360 degrees view - Private jacuzzi on the roof terrace - Private... View all property information
    Location Information
    Simpson Bay, Sint Maarten 00000
    5 of 5 bubbles Reviewed February 18, 2015
    Great place for two couples. Close to lots of restaurants and great beaches. Condo had everything we needed and expected. Building was secure & private, had reserved parking...
    5 of 5 bubbles Reviewed September 15, 2014
    My extended family of 8 adults and 1 child just came back from our trip to St Marteen. The condo was exactly how the picture portrayed it to be... Just amazing! I was skeptical at...
    See all reviews
    1 / 20
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Grill
    • Shared Outdoor Pool...
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Stylish , furnished 2 bedrooms, townhouse in quiet, residential area in Pelican, Rancho cielo Estates, Bathroom newly renovated with bath and rain shower, large master bedroom with furnished veranda with unobstructed ocean view. Walk-in closet. Very large open plan kitchen, courtyard with exotic... View all property information
    Location Information
    Simpson Bay, Sint Maarten 000000
    5 of 5 bubbles Reviewed January 2, 2014
    I stayed at this villa with my family over the Christmas break. We had a fantastic time. My kids (10 and 7) enjoyed it very much. The place is very spacious and beatifully...
    See all reviews
    1 / 11
    5 of 5 bubbles (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Patio
    • Shared Outdoor Pool...
    • Balcony
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    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... View all property information
    Location Information
    Simpson Bay, Sint Maarten 00014
    5 of 5 bubbles Reviewed June 18, 2014
    We stayed in Jackies Appartement for 10 days. The Appartement is new renovated and has a nice littel Balkony surrounded by palm trees. It has a brand new shower with different...
    See all reviews
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    1 / 26
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Balcony
    • Internet Access
    • Parking
    • Grill
    • Terrace
    • Shared Yard
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our Reservation Payment Protection Guarantee ensures you peace of mind. Preferred Escapes is a licensed & registered villa wholesaler. (TICO) #50020229. (http://www.tico.ca/) Our Service Guarantee ensures you the best villa experience. (http://www.preferredescapes.com/service-guarantee) This 6... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 8
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Internet Access
    • Satellite TV
    • Balcony
    • Terrace
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    This 1 bedroom/1bath unit is located in Pelican Key/Simpson Bay' next to LaVista Resort. Within walking distance to many restaurants, bars, grocery store and casino. The unit has a full kitchen with all the comforts of home, a queen size sleeper sofa and a bedroom with a queen bed, comfortably... View all property information
    Location Information
    Simpson Bay, Sint Maarten 00090
    1 / 8
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Air Conditioning
    • Parking
    • Balcony
    • Shared Outdoor Pool...
    • Outdoor Dining Area
    • Washer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Lovely modern 2 bed, 2.5 bath modern condo in gated complex with pool, Large fully furnished modern kitchen with great breeze, ceiling fans and air conditioning. Large porch off the living area and also the master bedroom.<BR>Located close to lots of wonderful restaurants, night clubs, movies,... View all property information
    Location Information
    Simpson Bay, Sint Maarten 00000
    1 / 61
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Balcony
    • Grill
    • Air Conditioning
    • Shared Yard
    • Internet Access
    • Terrace
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our Reservation Payment Protection Guarantee ensures you peace of mind. Preferred Escapes is a licensed & registered villa wholesaler. (TICO) #50020229. (http://www.tico.ca/) Our Service Guarantee ensures you the best villa experience. (http://www.preferredescapes.com/service-guarantee) Speranza,... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 61
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Shared Yard
    • Internet Access
    • Grill
    • Balcony
    • Air Conditioning
    • Terrace
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our Reservation Payment Protection Guarantee ensures you peace of mind. Preferred Escapes is a licensed & registered villa wholesaler. (TICO) #50020229. (http://www.tico.ca/) Our Service Guarantee ensures you the best villa experience. (http://www.preferredescapes.com/service-guarantee) Speranza,... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 23
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • DVD Player
    • Washer
    • Waterfront
    • Satellite TV
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This unique oceanfront getaway close to the all the action that makes St. Martin/Sint Maarten so famous,will transport your mind and spirit to peaceful and memorable holidays. Ocean shore condo sleeps four in two bedrooms. This two bedroom, two bathroom condo combines breathtaking view of the... View all property information
    Location Information
    Simpson Bay, Sint Maarten 007
    4 of 5 bubbles Reviewed March 18, 2015
    This villa is literally perched on the edge of the ocean. Two large bdms with spacious baths, large kitchen and living area. Balcony overlooks ocean and there is a private...
    See all reviews
    1 / 17
    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool...
    • Ocean Views
    • Satellite TV
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Nestled on top of Pelican Key on Sint Maarten is Son Risa Penthouse; where spectacular views of of the Caribbean Sea await you. This tropical oasis is set just far enough from the entertainment neighborhood to allow for quiet relaxation while still with in walking distance of restaurants, bars,... View all property information
    Location Information
    Simpson Bay, Sint Maarten PELICAN KEY
    5 of 5 bubbles Reviewed March 13, 2016
    We recently returned from a three-week stay at this Penthouse and we give it an "A Plus" rating. The property is lovely, and exactly as shown in the photos. It is very comfortable...
    5 of 5 bubbles Reviewed February 7, 2014
    I really enjoyed staying at this condo. The location was very convienent and the condo had all of luxuries of home! (Really nice). The view from the balcony was priceless...
    See all reviews
    1 / 48
    5 of 5 bubbles (2) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • DVD Player
    • Ocean Views
    • Balcony
    • Grill
    • Waterfront
    • Housekeeping...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    A modern tropical retreat in an enclave of privacy offering breathtaking views over the Caribbean sea. Located a few minutes drive away from: - Hollywood Casino - Buccaneer Beach Bar BBQ - French Bakery The Taste Factory serving breakfast all day and lunch, Take a stroll on the beach, shopping... View all property information
    Location Information
    Simpson Bay, Sint Maarten 00000
    5 of 5 bubbles Reviewed April 22, 2016
    This beautiful Villa is close to all of the places that we like to go, You are close to the bars and restauraunts in Simpson's Bay, The airport and Maho are a short drive. The...
    5 of 5 bubbles Reviewed January 17, 2016
    What a great place Michael was amazing We had a small problem we called Michael and he was shortly and had it fixed and followed to make sure everything was working well
    See all reviews
    1 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor...
    • Satellite TV
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Mountain Views
    • Ocean Views
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Simpson Bay, Sint Maarten NA
    1 / 26
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Ocean Views
    • Housekeeping...
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Simpson Bay, Sint Maarten ST MAARTEEN DWI
    5 of 5 bubbles Reviewed February 23, 2016
    I have stayed here 3 times and I am going back in Oct 2016 for TWO weeks! I am so thrilled w/this resort and rooms to stay in. The food is awesome and reasonably priced. The...
    See all reviews
    Get the List
    1 / 28
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Shared Outdoor Pool...
    • Satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    "At Seaside" is our dream...make it yours too! Serene Caribbean views can be enjoyed from the terrace. She is one of 20 units in a gated community surrounding a pool with views of the Caribbean. The grounds are lush and well tended. There is a king-sized bed and master bath off the bedroom. There... View all property information
    Location Information
    Simpson Bay, Sint Maarten 000
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping...
    • Washer
    • DVD Player
    • Grill
    • Balcony
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This third floor end unit ON THE BEACH offers plenty of privacy along with magnificent ocean views. The intimate 12-unit complex has gated private parking as well as its own pool just steps from the sand. It sits beachfront just a short walk from restaurants and shopping of Simpson Bay. Karakter... View all property information
    Location Information
    Simpson Bay, Sint Maarten SX
    1 / 31
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Hot Tub
    • DVD Player
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Bayview Unit #3 is a perfect location, views from the terrace are expansive taking in the wonderful views of the of the Caribbean Sea.As you enter the property, the first thing you will see is the amazing view of Simpson Bay, St. Maarten's 2 mile long beach. There is a private pathway to the beach... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 33
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Satellite TV
    • Waterfront
    • Private Outdoor...
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    A beautiful new house in a new development, within a quiet gated community, with security onsite. Yet it is just a few minutes to great restaurants, duty free shopping, casinos, spas and grocery stores. And only 10 minutes from Princess Julianna Airport. Our 3 bedroom house comfortably sleeps 6... View all property information
    Location Information
    Simpson Bay, Sint Maarten NA
    5 of 5 bubbles Reviewed February 4, 2016
    We were a group of 4 people, staying in the house for one week and we didn't have any issues with it. The house had everything we needed. It is located on the perfect place, with...
    See all reviews
    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Patio
    • Parking
    • Wi-Fi
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    10 Nights Minimum Requirement - Travel From Dec 15 - Jan 4, 2017...Practically roll out of bed on to the soft white sand of Simpson Bay beach!! Beachside is a very comfortably furnished 3 bedroom, 3 bath condo located directly on beautiful Simpson Bay beach! Beachside is the best located unit at... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 14
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Patio
    • Satellite TV
    • Shared Outdoor Pool...
    • Wi-Fi
    • Air Conditioning
    • Washer
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    7th Night Free! May 1 - Nov 15, 2016SBBC #3 is a 2 bedroom, 2 bath St. Maarten vacation rental located right on the beach at beautiful Simpson Bay. One of only 12 units in it's development, it offers quiet and comfortable surroundings, and the ocean just footsteps away in Dutch St. Maarten. The... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 38
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Grill
    • Hot Tub
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    7 Nights Minimum Requirement - Travel From Dec 27 - Jan 6, 2017...Wow! Check out this HUGE amazingly affordable, fully air-conditioned BEACHFRONT villa nestled on Burgeoux Bay beach which offers what the name implies... gorgeous SUNSETS!! Villa Sunshine is a newly renovated vacation rental with 5... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 18
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Parking
    • Washer
    • Satellite TV
    • Balcony
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Simpson Bay is bordered by a beautiful 2-mile long, lightly-populated curved beach; Las Arenas is a very high-end 12-unit condominium complex right in the middle of Simpson Bay Beach (and one of the finest in St. Maarten); and this third-level unit, “Heaven”, is a premium unit within Las Arenas.... View all property information
    Location Information
    Simpson Bay, Sint Maarten 000000
    1 / 19
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Washer
    • Private Outdoor...
    • DVD Player
    • Patio
    • Satellite TV
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Rates vary depending on # of bedrooms rented. Please see rate table or call for details.Crystal clear turquoise sea flecked with dazzling tropical sun, powdery white sands stretching along one of St Maartens longest beaches; Lush exotic foliage surrounding an elegant building of architectural... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    5 of 5 bubbles Reviewed March 1, 2016
    10 days of paradise and bliss. Unit is on main floor steps from the beach and ocean. Sunsets were amazing each night. Hot tub on deck and BBQ were great! Underground...
    5 of 5 bubbles Reviewed May 29, 2015
    4 of us stayed her the week of May 17/15 and had fantastic time. The unit has loads of space for 2 couples - we never felt like we were on top of each other. The kitchen is...
    See all reviews
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Ocean Views
    • Terrace
    • Patio
    • Balcony
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    ◾first floor direct access to the pool and beachfront ◾amazing 3 ½ mile crescent of powdery white sand beach with gentle waves ◾private pool front lanai accessible from the master bedroom and living area ◾large, fully functional kitchen, all granite ,new, top grade appliances and all kitchen... View all property information
    Location Information
    Simpson Bay, Sint Maarten NONE
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Housekeeping...
    • Air Conditioning
    • Grill
    • Washer
    • Wi-Fi
    • Ocean Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This one-bedroom condo unit is located in beacon hill on the ocean with views from both sides of the unit with view that only one could dream about. You are within shorts distance and even walking distance should I say to great beaches such as the Simpson bay beach or mullet bay beach. The condo... View all property information
    Location Information
    Simpson Bay, Sint Maarten 9999 XX
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Satellite TV
    • Patio
    • Washer
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Simpson Bay Beach Condo #2 is a beautiful ground floor, well equipped, fully air-conditioned condo located directly on Simpson Bay Beach. Walk off your patio and onto a wonderful soft sandy beach! Enjoy quiet mornings with the birds singing or take an early morning stroll or dip on beautiful, two... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 40
    5 Bedrooms, 7 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • DVD Player
    • Private Outdoor...
    • Satellite TV
    • Internet Access
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Welcome to Diamond Hill Estate and Villa Diamond Chateau...This villa offers unparalleled privacy, breathtaking views of Simpson Bay Lagoon, Juliana Airport, the Caribbean Sea and Anguilla in the distance. The villa is at a central location overlooking the Simpson Bay harbor with easy access to... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 23
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    • Private Outdoor...
    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    7 Nights Minimum Requirement - Travel From Dec 15 - Jan 4, 2017...CASA DE BELLA is a very comfortable, fully air-conditioned 3 bedroom, 2 ½ bath townhome with views towards Simpson Bay and the Simpson Bay Lagoon... and it has a private pool! It is conveniently located an easy, short walk to a... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    5 of 5 bubbles Reviewed February 4, 2015
    We decided to rent a villa/house instead of staying in a all-inclusive because we were a group of 5 friends to enjoy a more local experience. We were situated in Simpson Bay...
    See all reviews
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Patio
    • Air Conditioning
    • Shared Outdoor Pool...
    • Satellite TV
    • DVD Player
    • Hot Tub
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    7 Nights Minimum Requirement - Travel From Dec 15 - Jan 4, 2017...Marisol is a light and airy St. Maarten vacation rental at Point Blue in Pelican Key Estate. With 2 bedrooms and 3 full bathrooms, this immaculate two storey townhouse provides a quiet and peaceful tropical oasis for your stay in... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to a wonderfully relaxing and romantic hideaway, CARISMA on the BEACH at Pelican Key... Charming yet classy; sophisticated yet very comfortable, it is perfect for couples and families! This newly renovated 2 bedroom, 2 bath villa has everything to make your vacation perfect... Gorgeous... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 13
    4.5 of 5 bubbles (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Waterfront
    • Satellite TV
    • DVD Player
    • Washer
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    7 Nights Minimum Requirement - Travel From Dec 15 - 29, 2016..."Unforgettable" is two bedroom, two and a half bathroom ground floor luxury St. Maarten vacation rental condo... is located in Las Arenas, a new contemporary, high quality complex on Simpson Bay Beach. The disappearing sliding glass... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    4 of 5 bubbles Reviewed November 16, 2013
    The beach was lovely the service at the beach and st the resort restaurants was great. There were places to go downtown. The prearranged trip downtown with one of the major...
    5 of 5 bubbles Reviewed July 15, 2013
    Our family of 3 spent a week in Unforgettable. It lives up to its name. The location is perfect, right on the beach in Simpson Bay. Our daughter is disabled and in a wheelchair...
    See all reviews
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool...
    • DVD Player
    • Satellite TV
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A Wonderful Place!!! Coco Beach Club #6 beach front St. Maarten vacation rental, Dutch St Maarten , Simpson Bay Beach, near Maho night life.Wake up in the morning and walk right out onto the beach at Simpson Bay when you stay at this new 2 bedroom 2 bath St Maarten rental condo. Coco Beach #6 has... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 43
    5 of 5 bubbles (4) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Outdoor Dining Area
    • Grill
    • Private Outdoor...
    • Waterfront
    • Air Conditioning
    • Washer
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Caribbean Blue is a beachfront villa in Pelican Key. With five bedrooms and five and a half bathrooms, it is a perfect house for a family vacation! The deck at Caribbean Blue is the perfect spot for enjoying the sun and sea, and has wonderful views of the island of Saba, and of the sunset. Pelican... View all property information
    Location Information
    Simpson Bay, Sint Maarten 78866
    5 of 5 bubbles Reviewed October 12, 2016
    My family of 8, two daughters & a son and there spouses, and my husband and I stayed here for 10 days starting on Boxing Day. We cannot say enough about this beautiful property...
    5 of 5 bubbles Reviewed January 7, 2014
    Caribbean Blue is the perfect beachfront home. We spend most of our time around the pool. Also, the location of this home is great, close to restaurants, beach bars, and massages...
    See all reviews
    1 / 16
    4.5 of 5 bubbles (9) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    Show Prices
    Amenities & Details
    • Patio
    • Shared Outdoor Pool...
    • Internet Access
    • DVD Player
    • Washer
    • Air Conditioning
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    We offer privacy in this safe, romantic, Coral Shore setting at the outside edge of Pelican Key, where you are so close to beaches, shopping, restaurants, casinos and water sports activities. Swim, fish, and snorkel right in front of your own villa. Large pool with lounging areas, too. We... View all property information
    Location Information
    Simpson Bay, Sint Maarten 00000
    5 of 5 bubbles Reviewed August 15, 2016
    We had a very good time in the villa. It is a perfect and quiet location with nice garden and swimming pool. The pool area was very nice renovated before our arrival (july 24th...
    5 of 5 bubbles Reviewed June 22, 2012
    We were very pleased with our stay at Tres Belle Villa. We stayed for 5 nights, but wish we had stayed longer. This was a perfect location, we were able to drive to multiple...
    See all reviews
    1 / 41
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Washer
    • Satellite TV
    • Internet Access
    • DVD Player
    • Private Outdoor...
    • Sauna
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    “The Reef “ is a beautiful 5 bedroom contemporary villa, superbly positioned on the Simpson Bay Lagoon on the Dutch side of the island of St. Martin/St. Maarten. The villa has its own private boat dock, an amazing lounging terrace with very private exterior living areas and a beautiful waterfront,... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 29
    3.5 of 5 bubbles (2) Average
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Waterfront
    • Grill
    • Hot Tub
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    7 Nights Minimum Requirement - Travel From Dec 15 - 29, 2016...Atlantis at Coco Beach Club is a great location for your vacation! Located right on the beach at Simpson Bay, you will wake every morning to the sound of the ocean. Atlantis at Coco Beach Club is a one bedroom St. Maarten rental condo,... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 18
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Ocean Views
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    About this property
    Beautiful beach side apartment with spectacular ocean view in Simpson Bay.<BR>Come stay and enjoy the beautiful sunsets and relax on the beach!<BR>Surrounded by top rated restaurants, bars, supermarkets, casino's and nightlife.<BR>Private car parking.<BR>Child friendly.<BR>Fully equipped apartment,... View all property information
    Location Information
    Simpson Bay, Sint Maarten 11111
    5 of 5 bubbles Reviewed April 30, 2016
    Loved Martine's apartment! It is right across the road from the beach and close to all the sights and ammenities in Simpson Bay. Martine was excellent to deal with and she made...
    5 of 5 bubbles Reviewed April 12, 2015
    This is a return trip to this apartment, that is how much we have liked it in the past. This trip again, we had a wonderful time. The apartment is is big enough for 4, with all...
    See all reviews
    1 / 29
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Waterfront
    • Patio
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    7 Nights Minimum Requirement - Travel From Dec 15 - Jan 4, 2017...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....The terrace, full of... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    5 of 5 bubbles Reviewed August 10, 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...
    See all reviews
    1 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • Washer
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Every 5th Night Free! May 26 - Dec 16, 2016Restrictions ApplyEvery 7th Night Free! Jan 7 - Dec 15, 2017Restrictions Apply Rates are based on 2 guests per bedroom and p/additional person on the sofa bed (maximum 4 additional persons allowed) - $140.00 p/person, p/week (Summer/Fall); $175.00... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 30
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Private Outdoor...
    • Washer
    • Waterfront
    • Satellite TV
    • DVD Player
    • Outdoor Dining Area
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Built on a cliff, directly above the tropical blue sea. The luxury rental Villa Tara offers vacationers a 'one of a kind' experience. The backyard of this home is the majestic Caribbean Sea, and it can be admired from almost every room in this villa. Cleverly designed pocket doors allow you to open... View all property information
    Location Information
    Simpson Bay, Sint Maarten 78866
    1 / 33
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Grill
    • Outdoor Dining Area
    • Waterfront
    • Private Outdoor...
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Faja Lobie has become a very popular rental home over the last two years. This beautiful, newly renovated three bedroom, three bath villa sits directly on Bourgeaux Bay beach in the residential area of Beacon Hill on the Dutch side. This home offers a wonderful combination of indoor and outdoor... View all property information
    Location Information
    Simpson Bay, Sint Maarten 78866
    1 / 31
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Waterfront
    • DVD Player
    • Patio
    • Shared Outdoor Pool...
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Royal Palm 101 is a ground floor 3 bedroom, 3 bath St. Maarten vacation rental that opens up to the beach and the pool area... Great for kids! Royal Palm Beach Club in Simpson Bay, Dutch St. Maarten is situated on the ocean a few steps away from a beautiful stretch of sandy beach. Enjoy spectacular... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    5 of 5 bubbles Reviewed May 13, 2016
    The condo was perfect for our family of 5. The view was to die for! Corner unit, watching the yachts come & go all day long! The best spot in the complex. Also enjoyed the...
    See all reviews
    1 / 10
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Private Outdoor...
    • Satellite TV
    • Waterfront
    • Hot Tub
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Rates may vary depending on # of bedrooms rented. Please see rate table or call for details.Daffodil is a multi million dollar beautiful 5 bedroom 5 bath oceanfront St Maarten vacation rental villa that features colorful tropical furnishings and decorations with 5 full king bedrooms and 5 luxurious... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    1 / 61
    5 of 5 bubbles (1) Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Waterfront
    • Satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Simpson Bay, Sint Maarten
    5 of 5 bubbles Reviewed October 14, 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.....
    See all reviews