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Villa vacation rentals in Simpson Bay

Find and book unique villas on Airbnb

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Popular amenities for Simpson Bay villa rentals

Private villa rentals

Top guest favorite
Villa in Collectivity of Saint Martin
5 out of 5 average rating, 74 reviews

VILLA I LOVE VIEW - villa luxe avec vue mer

TinaRating, 5 stars2 days ago
The place was perfect, and the view and backyard were the highlights of our stay! We were just 5 to 10 minutes away from the best beaches and activities on the French side. The supermarket and an amazing bakery were only about 4 minutes down the road, along with a wine store. On the first day, I struggled to get my phone to work with Google Maps because I hadn't informed my cell phone company that I would be traveling abroad. However, the hosts were incredibly helpful in assisting me. The husband stayed on the phone with me the entire time, which made a world of difference since I was really anxious about my first Airbnb experience in the Caribbean. Once I sorted out the issue with my cell carrier, we were able to navigate all over the island easily. I would definitely stay here again, and I can't wait to come back!
Top guest favorite
Villa in Cul-de-Sac
5 out of 5 average rating, 23 reviews

Villa Pure - 3 BR waterfront with kayaks, wifi, AC

PhilRating, 5 stars3 weeks ago
The villa was absolutely beautiful! Exactly as described and the view was incredible. The villa had everything we needed and had plenty of toys for the kids and amenities to have fun on the water. The pool was great for the kids and the beach in the backyard was a nice added bonus. Nina was a great host as well!
Guest favorite
Villa in Saint Martin
4.98 out of 5 average rating, 44 reviews

Villa SEA VIEW, 5' from Grand Case beach, privacy

JanaRating, 5 stars1 month ago
Amazing place, beautiful house with lots of amenities. Elodie was very responsive and even provided some extra amenities for our kids. The view is fantastic and our kids loved the heated pool. It’s a perfect place to watch the sun set. The house offers a few shady spots during the day but not too much. Very spacious inside. Kitchen has everything you need and is well equipped. Large and comfortable beds! Having kids, the layout of the house is great, all is on one floor. The only small downside is the noise from the street, it’s not too much and not very disturbing but fast cars or construction work is noticeable when relaxing on the terrace. Overall I would definitely recommend the place!
Guest favorite
Villa in Upper Prince's Quarter
5 out of 5 average rating, 54 reviews

EXQUISITE 5-STAR BEACHFRONT VILLA

AriRating, 5 stars1 month ago
We just returned from an unforgettable week at Villa Corrine in Sint Maarten, and I honestly don’t know where to begin—it was that incredible. This villa is everything you dream about when you think “luxury oceanfront escape,” and then some. From the moment we arrived, we were blown away. The privacy, the jaw-dropping views, the elegant decor—every detail of Villa Corrine is curated to perfection. Whether you're lounging by the pool with the ocean as your backdrop, enjoying a morning coffee with the breeze flowing through the open spaces, or simply relaxing in one of the beautifully appointed rooms, you feel like you're in your own private paradise. And the view? Let's just say waking up to that ocean every morning felt like a dream. This magical villa was one of the most relaxing, rejuvenating spaces that we’ve ever stayed at. Five stars simply don’t feel like enough. Thank you for sharing this incredible space with us!
Superhost
Villa in Cole Bay
5 out of 5 average rating, 9 reviews

Caribbean View Villa - Sea - Sunset - Location#1

JohnRating, 5 stars3 months ago
Great space, great location, and great views! There isn't much else to say as everything was as described and Joy was a great host. We look forward to visiting again next year.
Guest favorite
Villa in Collectivity of Saint Martin
4.96 out of 5 average rating, 46 reviews

Villa KALYA - Orient Bay - 3 bedrooms

CynthiaRating, 5 stars2 weeks ago
My friends and I had a wonderful time at Clea's place. The house is beautiful. She had cold beverages waiting in the refrigerator for our arrival and the scenery was beautiful from the veranda. our only concerned is that the pool is not clearly marked for depth. I'm about 5 ft and the pool all the way around is a little deeper than that which is over my head. There is no shallow end. Orient Beach is very nice. one drawback is the constant haggling for a beach massage by the locals. I had to exercise a gentle rudeness in order for them to leave us alone. Other than that we had a fabulous time. You must visit the African Market in Phillipsburg. You will find beautiful African artifacts at good prices. Anthony and Florence are the best.
Superhost
Villa in Collectivité de Saint-Martin
5 out of 5 average rating, 3 reviews

Villa Litchi | Collection Villas Saint-Martin

OnurRating, 5 stars2 months ago
One of the best stays I’ve ever had on Airbnb! The villa was even more beautiful than the pictures — spacious, clean, and thoughtfully designed. I especially loved the stunning view and the outdoor shower, which made the experience feel even more special. Our host Marie was incredibly friendly and helpful, making us feel welcome from the moment we arrived. I wouldn’t hesitate to stay here again. Highly recommended!
Top guest favorite
Villa in Lower Prince's Quarter
5 out of 5 average rating, 27 reviews

Mountain View

RonequaRating, 5 stars1 month ago
Soo nice had to do it twice! Would definitely recommend!

Luxury villa rentals

Top guest favorite
Villa in MF
4.99 out of 5 average rating, 92 reviews

Your Paradise Villa

YanRating, 5 stars1 month ago
We had an absolutely amazing week at Your Paradise Villa in St. Maarten! The villa was stunning, perfectly clean, and had breathtaking views. Every detail was thoughtfully arranged, making our stay incredibly comfortable and relaxing. We can’t wait to come back! We would like to extend our heartfelt thanks to Denis, the gracious owner of Your Paradise Villa. Your exceptional hospitality and thoughtful gestures made our stay truly unforgettable. The special gifts and treats you provided were delightful surprises that added a personal touch to our experience. Your attention to detail and genuine care ensured that every moment of our week in St. Maarten was filled with comfort and joy. Thank you, Denis, for going above and beyond to make our vacation so special.
Guest favorite
Villa in Collectivity of Saint Martin
5 out of 5 average rating, 30 reviews

OOF villa d’architecte vue mer face à l’îlet Pinel

DavidRating, 5 stars1 month ago
The villa was an oasis among beautiful surroundings. We loved our stay and would definitely recommend this listing to anyone looking for a place to stay in St Martin!
Top guest favorite
Villa in Cul-de-Sac
5 out of 5 average rating, 10 reviews

Belle Lurette, 3 BR, pool, Pinel island bay, kayak

HeatherRating, 5 stars1 month ago
Our house was amazing from the pool to the scenery and how close it was on the water and to Pinel Beach! Philippe was the best host as well. He was there to greet us early, and went over everything in the house. Gave us beer, and a bottle of their native rum too! I would absolutely recommend this house and Philippe as a host!
Luxe
Villa in Les Terres Basses
4.88 out of 5 average rating, 8 reviews

Mariposa

BridgetRating, 5 stars10 months ago
I recently had the pleasure of staying at this lovely beach rental, and I can't say enough good things about the experience. From the moment we arrived, we were greeted with warm hospitality from Mehdi, our host. He went above and beyond to make sure we felt welcome and had everything we needed for a comfortable stay. The house itself was spotless, thanks to Agatha, the diligent housekeeper. Every corner of the rental was immaculately clean, and it was evident that she takes great pride in her work. The beach views were stunning, and the amenities provided were top-notch. Mehdi was always available to answer any questions and offer local tips, making our stay even more enjoyable. Agatha's attention to detail ensured that we felt right at home. If you're looking for a relaxing beach getaway with exceptional service, I highly recommend this rental.
Superhost
Villa in Little Bay
5 out of 5 average rating, 3 reviews

Luxury 3 Bedroom Ocean View Villa With a Pool.

ShakoraRating, 5 stars3 months ago
Villa Kimon is perfect! This beautiful villa was spacious with a suite for everyone, a pool and featured an incredible view that you simply do not want to miss. Not to mention, Manoj was incredibly helpful with local recommendations and responsive to our many questions! This is an exactly what you need for your SXM holiday. Stop researching and book today!
Superhost
Villa in Lowlands
4.96 out of 5 average rating, 25 reviews

Reflection Z 5 Star Villa

DavyRating, 5 stars1 month ago
Jamila est une super hôte, a pris le temps de me faire visiter la villa idéalement placée avec une vue extra sur l’aéroport le lagon et Maho beach.
Top guest favorite
Villa in MF
4.96 out of 5 average rating, 57 reviews

Private Orient Bay Villa with Spectacular Views

MimRating, 5 stars1 month ago
We had an absolutely wonderful stay. This was our first time to St. Martin. The house was perfect for us and even more beautiful in person. The view is amazing. They island was amazing. A short walk down the hill to access the beach, restaurants and stores was great. Dan and Flo were wonderful, helpful and very responsive. Would highly recommend this house to anyone looking to stay in this area. We can't wait to come back!
Superhost
Villa in Simpson Bay
4.75 out of 5 average rating, 4 reviews

Villa Saint-Tropez Breathtaking Sea Views

TonyRating, 5 stars15 months ago
From the moment we booked this Villa everything was smooth. Communication was excellent but what stood out the most was how wonderful this place was. With spectacular views and everything we needed for our stay, if you don't mind a bit of a hike, activities and restaurants were relatively close by.

Villa rentals with a pool

Guest favorite
Villa in Collectivity of Saint Martin
4.94 out of 5 average rating, 17 reviews

Newly Renovated! Villa Paradis - Unbeatable views.

RodRating, 5 stars2 months ago
This property is perfect for one or two couples. Ideally located near Marigot and Grand Case, and within 30 minutes to Orient and Anse Marcel. Beautiful views of Marigot Port area and coastline from the generous wrap around porch. Tess and team are some of the best hosts we've ever encountered. (we've stayed at more than one dozen villas throughout the Caribbean). H The Welcome Book is fit for professional publication. Extremely good detail on restaurants, shopping, TTD'S, etc. Decent pool and surrounding patio. Interior of villa is new and fresh and clean. All things work! Quiet neighbors (not a place to bring loud friends) The French side Rocks and this Villa is perfect in all ways. We will be back.
Top guest favorite
Villa in Les Terres Basses
5 out of 5 average rating, 27 reviews

Brand new! - Slowlife - Enjoy Villa

JonathanRating, 5 stars3 weeks ago
The Airbnb was exactly what we needed and more private and beautiful than we expected. The host was responsive and very helpful about making our experience unforgettable. Thank you so much!
Guest favorite
Villa in Saint-Martin
4.95 out of 5 average rating, 20 reviews

Villa Pineapple - Grand Case Area -5mn Orient Bay

DicksonRating, 5 stars3 months ago
A great villa, centrally located just outside Grand Case. Spotless and well equipped. Véronique was very responsive to any and all questions. Highly recommend!
Villa in Cole Bay
4.86 out of 5 average rating, 37 reviews

3 Bed & 3 Bath Villa Domila with Private Pool SXM

LisaRating, 5 stars2 weeks ago
⭐️⭐️⭐️⭐️⭐️ Our stay at Villa Domila in Sint Martaan was nothing short of perfection! From the moment we arrived, we were enveloped in an atmosphere of tranquility and luxury. The villa's location is ideal, just a stone's throw away from pristine beaches, making it easy to soak up the sun and enjoy the crystal-clear waters. A special mention must go to Davin, the property manager, who truly went above and beyond to make our experience unforgettable. He greeted us at the airport with a warm smile and took care of our transportation needs, providing a convenient car service that allowed us to explore the beautiful island effortlessly. The villa itself is a stunning retreat, beautifully decorated and equipped with all the amenities one could wish for. Whether lounging by the pool or enjoying a sunset from the terrace, every moment felt like a dream. We will definitely book again!
Guest favorite
Villa in Collectivité de Saint-Martin
5 out of 5 average rating, 7 reviews

Sunset, beach walk, full AC, US Cable

BarbaraRating, 5 stars2 weeks ago
This place is amazing. Feels like a luxury hotel yet is a villa. Like brand new. service level is outstanding. Anything you want they are there for you. Is waiting to greet you and every day available to answer questions about the island or book reservations for you. Includes cleaning staff..pool guy and groundskeeper. Happy Bay is a 10 min walk along a path and we'll worth it for swimming in clear turquoise water with very few people on the beach. He even had beverages in the frig for our use all week..lots of them. Large grocery store about 10 min drive. Rent a car and it will include someone waiting at the airport for you and your rental will be sitting at the villa for you. Bring mosquito spray ..they are tiny but annoying. You won't be disappointed in renting Villa Be Happy..it is luxurious.
Guest favorite
Villa in Residence Hope Hill
4.97 out of 5 average rating, 31 reviews

Villa Azur, great view of the Orient Bay

IdaraesitRating, 5 stars2 months ago
Wait until you see the view! The photos can’t do it justice. The house was clean, comfortable, and so close to the best places to visit on the French side. Highly recommend!
Superhost
Villa in Orient Bay
4.93 out of 5 average rating, 15 reviews

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

KarinaRating, 5 stars1 month ago
Stunning house in the best location in St. Martin! The house was beautiful and clean with an amazing pool. I don’t think I’ve seen a better stocked kitchen between utensils and spices! I also appreciated the games for kids that were readily available. The house is an easy 10 min walk to the beach and fantastic restaurants. I loved getting my daily pastries and baguette at the local bakery and having breakfast outdoors with an incredible view. Thank you for hosting us! We had a wonderful time.
Villa in Cole Bay
4.76 out of 5 average rating, 33 reviews

A heavenly Sint Maarten's retreat

JasmenRating, 5 stars1 month ago
The description is nothing compared to how beautiful the place and scenery truly is. Words can’t express. “GWEN IS AN ANGEL” I loved her energy. She took us on a wonderful tour around the house , gave us safety tips pointed out everything we needed to know (including the monkeys in the morning ) for the 5 days we stayed , Any concerns or issues Gwen responded and handled it quickly. The rooms were big and clean with perfect size beds. The pool was my favorite part it is absolutely amazing at night with the lights and the sunset view. The house came with everything you needed from mosquito spray to board games , cards etc. we also loved that the supermarket was just down the road. This was truly a serene comfortable and cozy house to stay in and it was everything I needed to celebrate my 40th birthday. I had such a great time I would love to come back at least once a year :)

Quick stats about villa rentals in Simpson Bay

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$31,473 GYD before taxes and fees

  • Total number of reviews

    260 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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