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Villa vacation rentals in Simpson Bay

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Popular amenities for Simpson Bay villa rentals

Private villa rentals

Guest favorite
A sunlit terrace features red cushioned seating arranged around a coffee table, surrounded by vibrant greenery and rock formations. The tiled floor reflects the light, enhancing the outdoor living space, which offers a serene atmosphere for relaxation or social gatherings.

Villa in MF

4.99 out of 5 average rating, 86 reviews

Your Paradise Villa

JimRating, 5 stars2 weeks ago
Denis was the best host we’ve had at any Airbnb. He picked us up at the airport, provided some wine & fruit, and was extremely helpful and responsive. When our coffee maker stopped working he brought a replacement immediately. We were very impressed with Denis!!!
Guest favorite
A spacious living area is filled with natural light, featuring light wooden furniture and tasteful decor. Large glass doors offer views of the outdoor space. A cozy seating arrangement invites relaxation, while decorative plants and a stylish rug enhance the tranquil ambiance.

Villa in Orient Bay

5 out of 5 average rating, 47 reviews

ORIENT BAY🌴 BEACH VILLA 5🌴ONLY BEACH ACCESS 🌴🌸🐚

CharlieRating, 5 stars1 month ago
Our stay at Sarah's Airbnb was great. everything very confy, and the walking distance to the beach is amazing. The house was great and all 9 of us enjoyed our stay there. Fred and Sarah were always eager to help if needed, and we are very thankful for their hospitality!!! Highly recommended!!
Guest favorite

Villa in Saint Martin

4.88 out of 5 average rating, 24 reviews

Villa Zabricot with pool- sxm island vacation

MarieRating, 5 stars1 week ago
The place is gorgeous. Exactly as in the pictures. We had a few hiccups with one of the bathrooms and in the kitchen but Emma was able to fix it immediately! I would definitely recommend this place to friends and family.
Guest favorite
The outdoor patio features two lounge chairs with striped cushions, offering a place to relax while enjoying views of the surrounding landscape. Large glass doors provide access to the open-concept living area filled with natural light.

Villa in Upper Prince's Quarter

4.98 out of 5 average rating, 57 reviews

Sea Haven Villa - Breathtaking Views of Dawn Beach

EmilyRating, 5 stars3 weeks ago
Esheen and David’s home is one of the most beautiful and comfortable Airbnbs we have ever stayed in! The home was incredibly clean and full of great amenities like beach chairs/umbrellas/coolers for an easy day at the beach. We loved waking up to the sounds of the ocean and lounging by the pool each morning. The location is perfect - tucked away from the hustle and bustle - and with unmatched views of the ocean. Esheen was an amazing hostess who was always immediately available for anything and was kind enough to provide great local tips and recommendations. She even provided the name of a captain doing small shared charters around the island which was the highlight of our trip! Thank you so much Esheen and David!
Superhost
An inviting outdoor area features a crystal-clear pool surrounded by several sun loungers. A shaded seating area is visible, along with an outdoor dining space. Lush greenery and stone walls enhance the tranquil setting, offering a serene backdrop of hills and blue skies.

Villa in Cul-de-Sac

4.88 out of 5 average rating, 24 reviews

Villa Chloé SXM - Beachfront & Pinel view 🌴☀️🐬

KatherineRating, 5 stars5 months ago
This is the most wonderful Airbnb for vacations! Here are some of the best parts: the pool, the private and beautiful back patio (with iguana sightings) that overlooks the water, the kayaks to Pinel, the snorkelling equipment, the kitchen (design and very nice appliances), 3 super comfy and perfect rooms for sleeping with king beds, the location - short trip to anse marcel, orient bay, grand case and access to awesome hiking (troussards trail with donkeys). Our second time here and it just gets better. Merci Jeremy!
Superhost
A modern villa is positioned on a hillside, featuring clean lines and a minimalist design. The exterior includes expansive windows and a balcony that invites natural light. Lush greenery surrounds the property, contrasting with the bright blue sky overhead.

Villa in Sint Maarten

4.84 out of 5 average rating, 61 reviews

Villa Indigo Dream, Indigo Bay SXM

NatalieRating, 5 stars1 month ago
I’ve just come back from spending a week here for my 30th birthday and I cannot express how happy I am with the decision we made to stay here. From the moment we booked to the day we left the communication with Laura and the IRE team was amazing. When we arrived we were absolutely taken away by the views of the villa and waking up everyday to it was a dream! We were really impressed with how much food/amenities the Airbnb had stocked and ready! For a group of 4 we found the villa very spacious, clean and enjoyed the pool everyday! This villa is located in a great part of the island with access to loads to beaches and restaurants but is also in very quiet residential area. The driveway is steep but our driver was able to get to the villa. Massive thanks again to the IRE team who quickly sorted out the small water issue we had and dropped off a small gift the next day. We really appreciated it and was a great highlight for my birthday! Overall I’ll definitely stay here again!
Guest favorite

Villa in Philipsburg

4.98 out of 5 average rating, 262 reviews

Villa Dream View Belair Sint Maarten SXM

AaronRating, 5 stars1 week ago
Eric and Rochellie were great hosts. You can tell they paid great attention to details when building the villa. Dream View was a fantastic home base as we explored the island. Loved the open air design and the layout of the house. The view is so amazing that we decided to just stay in the pool one day. Philipsburg is just around the corner for groceries and restraunts and you can reach most places in 20-25 min. Thanks again.
Guest favorite

Villa in Upper Prince's Quarter

4.91 out of 5 average rating, 46 reviews

Villa Blue Roc

MichaelRating, 5 stars1 month ago
This property is amazing! The view is stunning and the home is beautiful. We had a family of four plus grandparents and had plenty of room to spread out, cook dinners and enjoy the views and pool. It’s in a gated community and feels very safe. The only drawback is it’s a drive to get to restaurants, beaches , groceries, etc but the view and accommodations are well worth it. We would definitely stay again and Bruno and Isabelle went out of their way to make sure we had everything we needed.

Luxury villa rentals

Guest favorite

Villa in Simpson Bay

4.98 out of 5 average rating, 58 reviews

Waterfront "Bonjour" Beacon Hill St Maarten

LeeRating, 5 stars1 month ago
We loved our stay. Super nice and new house— kitchen was well equipped, beds were comfortable with great linens. Honestly we had no complaints. Gwen is responsive, informative and cheerful. We spent a lot of time at the beach near D’s beach bar and had lunch at D’s— the grilled fresh catch fish tacos were popular with us. We also had a chef one night who Gwen recommended—he was great. We had a car and drove all around the island. We hope we get to return to Villa Bonjour someday.
Superhost

Villa in Grandes Cayes

5 out of 5 average rating, 7 reviews

LIFE IS GOOD IN CUL DE SAC

MatthewRating, 5 stars8 months ago
Manu was an amazing host and so kind and helpful. The house is perfect with amazing views
Superhost

Villa in Anse Marcel

5 out of 5 average rating, 4 reviews

Secret Harbor Villa, Amazing place in Anse Marcel

GlendaRating, 5 stars2 weeks ago
Our stay at the Villa was absolutely lovely! This was our fourth visit to St. Martin and we love the island more each time we visit! The Villa was exactly as described and even more beautiful than the photos! We had a truly wonderful time and will absolutely book the Villa again!
Guest favorite
An aerial view of the villa showcases its unique architecture surrounded by lush greenery. A private pool is visible, along with various outdoor seating areas, dining spaces, and wooden walkways connecting the different levels of the home.

Villa in Collectivity of Saint Martin

5 out of 5 average rating, 25 reviews

OOF architect villa sea view facing Pinel Island

MattRating, 5 stars3 weeks ago
A wonderful place to stay! The house is private, peaceful and the rooms on separate levels was great for us and our friends. The photos don’t do it enough justice, the view overlooking the water and landscape is perfect!
Superhost
An open living area features a high vaulted ceiling with wooden beams. The space includes a modern sectional sofa with vibrant green and neutral cushions, a wooden coffee table, and a flat-screen TV. Large sliding glass doors lead to an outdoor dining area with ample seating.

Villa in MF

5 out of 5 average rating, 5 reviews

Villa Kiwi - Collection Villas Saint-Martin

MelissaRating, 5 stars2 months ago
This villa was absolutely stunning and had everything we needed for our stay, as two families with young children. It was minutes from the airport and close to many beautiful beaches and dining options. A car is necessary to get around. We spent lots of time in the pool, enjoying views of the ocean and the sunset in the evening. The villa was also immaculately clean and well maintained. Each room had its own bathroom, as well as an outdoor shower or bath option which we really enjoyed. The only thing to note is the entrance to the third bedroom is from the patio and not the villa itself. It wasn't a big issue for us however, as it was only a few short steps to the villa and we brought cameras to monitor our children in their room at night. All in all, we highly recommend this villa and would come back!
Guest favorite
A tranquil infinity pool reflects the evening sky, surrounded by a spacious deck and comfortable lounge chairs. The villa's partially covered terrace offers an inviting dining area, with lush tropical landscaping in the background and soft outdoor lighting enhancing the serene atmosphere.

Villa in MF

4.96 out of 5 average rating, 55 reviews

Private Orient Bay Villa with Spectacular Views

RomanRating, 5 stars4 months ago
Amazing experience from start to beginning everything was perfect. Parking space available right in front of the house which makes getting around easy. Essentials for the house are all provided , separate AC units in each bedroom and fully stacked kitchen. Pool is maintenance is twice a week and comes with various floating devices. Community is private and has many restaurants and small grocery store. Me and my family loved this property and the views of the Orient Bay. Make sure to look up Fish Market open from 8am to 12 if you are staying here, simply out of the world to have access to daily catches just a 5 min drive away. The Orient Beach is the BEST on the 🏝️ Florence (Flo) was very helpful with checkin and checkout and always available if needed. ⭐️⭐️⭐️⭐️⭐️
Guest favorite
The villa exterior is beautifully illuminated at night, showcasing a modern design with large glass doors. A private pool is visible, reflecting soft blue lights, while a cozy seating area beside the pool invites relaxation. The surrounding hillside is softly lit, creating a serene atmosphere.

Villa in Indigo Bay

4.91 out of 5 average rating, 33 reviews

Villa Elysian: Luxurious Ocean View in Indigo Bay

ElizabethRating, 5 stars1 month ago
Villa Elysian was simply perfect four our holiday vacation. The property was well maintained and had everything we needed — well-appointed kitchen, comfy beds and a gorgeous outdoor space plus lots of extras like cleaning products, spices & lots of chargers. The location was great get to drive to anywhere we wanted to go (island traffic is awful). The nearby beach is good and recommend reservations for beach chairs & meals in high season. Totally recommend and would return!

Villa rentals with a pool

Guest favorite

Villa in ORIENT BAY

5 out of 5 average rating, 18 reviews

Orient Bay villa

KristinaRating, 5 stars1 month ago
Overall a great stay in a nice location. There were a couple of things that need attention, some broken patio furniture, the bathroom door that does not close, but otherwise a nice stay.
A spacious villa is surrounded by lush greenery, featuring a large vanishing pool that reflects the sky. The outdoor area includes sun loungers and well-maintained gardens, with distant mountain views enhancing the serene setting.

Villa in Collectivity of Saint Martin

4.93 out of 5 average rating, 43 reviews

Hope Hill Villa - Monte Verde - Luxurious 4 B/R#

JenniferRating, 5 stars14 months ago
We had a wonderful family trip to Reeti’s gorgeous home. The view is unbelievable, far better than the photos can show, and the home is spacious, clean, private and comfortable. We enjoyed the stunning pool and the large kitchen as well as the ample outdoor space. It is ideally located a few mins drive from the shops and beach at Orient Bay and less than 10 mins from beautiful Friars Beach and the ferry to Pinel Island. The true highlight of our stay was working with Flo, the amazing concierge, who arranged dinner reservations, chairs at Yellow Beach on Pinel, organized a grocery delivery for us before we arrived and was incredibly responsive and helpful throughout our trip. Our experience was truly a dream and we would love to return.
Guest favorite

Villa in Cul-de-Sac

4.83 out of 5 average rating, 104 reviews

Pinel villa sea view 3 Bedrooms hot tub pool

CorinneRating, 5 stars1 week ago
We loved staying at the villa in cul-de sac! The home was a paradise within paradise. We spent so much time on the patio enjoying the views, enjoying coffee and reading, and lounging in the pool or hot tub. The beds and temp so comfy! Fred was our incredible host full of great recommendations, directions, and support. We were sad to leave what feels like a luxury home away from home. Bring in a private chef or a massage (we did both!) and revel in the delight of this home - you won’t regret it!
An outdoor lounge area features a green sofa surrounded by colorful cushions, complemented by wicker chairs. A glass-top table sits centrally, and lush greenery is visible beyond the arches, enhancing the serene setting.

Villa in Cul-de-Sac

4.84 out of 5 average rating, 32 reviews

Ocean front "colibris" amazing view

Leda & ElettraRating, 5 stars5 months ago
Beautiful villa with stunning ocean views, Located on a hill overlooking the bay of Cul-de-sac, Pinel Island and Tintamarre are both visible from the pool deck. The living room is very comfortable for a large living room and with 2 large sofas perfect for holidays for families or groups of friends. There are the best restaurants on the island and very beautiful beaches close to the villa. The neighborhood is very quiet and relaxing. Camille is a great host, she made sure we had everything we needed to have a great stay which was the case!! The views are really beautiful!

Villa in Collectivité de Saint-Martin

4.8 out of 5 average rating, 5 reviews

Villa OB - Beautiful Villa with Pool

JohnRating, 5 stars12 months ago
The villa was great. Very private except for the cameras. Make sure you ask up front for enough keys and remotes for the gate. Very comfortable beds. Great pool. Fantastic place to stay.
Superhost
A private pool is surrounded by a sun deck featuring lounge chairs and umbrellas, providing a shaded spot. Lush greenery and tropical plants complement the outdoor area, while a spacious covered terrace with a dining table is positioned adjacent to the house.

Villa in Orient Bay

4.92 out of 5 average rating, 13 reviews

Villa Saphir, 3 bedrooms, private pool and beautiful view!

MollieRating, 5 stars14 months ago
Christine’s place is beautiful. The location is fantastic, as it feels both quiet and peaceful and private, and yet close to anything and everything you might need/desire. It is a great space for a family (we traveled with two small children). Christine’s place is well-stocked with anything you might need, from spices in the kitchen to pool toys, a first aid kit, and other amenities. Highly recommend!
Guest favorite
An outdoor living area is furnished with comfortable sofas and armchairs, featuring decorative cushions. A table sits in the center for dining or leisure activities. Multiple palm trees and a colorful umbrella add to the relaxing ambiance. Views of nearby hills can be seen in the background.

Villa in Sint Maarten

4.98 out of 5 average rating, 60 reviews

*NEW* Villa Crystal Clear - Luxury Villa w/ Pool

CeliaRating, 5 stars1 month ago
This was my first time staying at an Airbnb and I’m converted! Crystal was an amazing host and so responsive and helpful. I felt as though I’ve known her for years! Her place was amazing and the views are breathtaking. Waking up to seeing blue water and three different islands from multiple rooms was just unreal. The private pool was A+ and my entire family loved every second of privacy and exclusivity. The neighborhood is quiet and the surrounding newly built homes at night was just a beautiful sight. The rooms were comfortable, the kitchen was super spacious and had every single thing we needed on a daily basis. Crystal was flexible with my concerns and always responded super fast on messenger. I felt like I was at my own home! She was a blessing and I will definitely return to her place again! 10/10!!!! Thanks again, Crystal <3

Villa in Saint Martin

5 out of 5 average rating, 3 reviews

Villa Moai - Pool & Sea View

ShivamRating, 5 stars1 month ago
We had a great stay at chloe's place -the place is even more beautiful than the pictures-our daughter loved it as well.Chloe was a great host and was always a text away -We will love to come back and stay here again .

Quick stats about villa rentals in Simpson Bay

  • Total rentals

    30 properties

  • Nightly prices starting at

    $200 before taxes and fees

  • Total number of reviews

    230 reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    30 properties have a pool

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