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Villa holiday rentals in Simpson Bay

Find and book unique villas on Airbnb

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Popular amenities for villa rentals in Simpson Bay

Private villa rentals

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

VILLA I LOVE VIEW – Luxury villa with sea view

TinaRating, 5 stars1 week 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!
Superhost
Villa in Cole Bay
4.86 out of 5 average rating, 43 reviews

Saint-Tropez With Ocean View - Boat Charter

TiffaniRating, 5 stars3 months ago
Perfect stay! Went with a group of 5 for my birthday absolutely loved everything about this Villa! From the views to the decor and the space. The location was close proximity to the beach and restaurants. Love it!
Top guest favourite
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 favourite
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!
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.
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!
Superhost
Villa in Indigo Bay
4.82 out of 5 average rating, 51 reviews

Infinity Views Indigo Bay SXM

RandallRating, 5 stars3 weeks ago
I want to start by giving a shout-out to the stellar hosts. They addressed an issue with the stove extremely promptly. After we left, Yulia notified me that I had left my headphones at the property and came to the airport to drop them off. That was truly above and beyond service and I am extremely appreciative. The property is well maintained and the view is gorgeous. The air conditioners were able to quickly cool the house when we returned from a day exploring. The driveway is a tad steep but nothing unmanageable, we were able to drive up to the apartment in a 2-wheel drive rental car. We stayed here for 10 days, half of the time working remotely and half on vacation. The wifi connection was stable and I had multiple video calls without issue. There was no dedicated work space but I used the kitchen table (and got to enjoy the view!) The only downside was another balcony located above the porch. It did not feel as private as we would have hoped. All said, we enjoyed our stay.
Guest favourite
Villa in Upper Prince's Quarter
4.92 out of 5 average rating, 25 reviews

Villa Seascapes, Stunning 180° Ocean view

RaenetteRating, 5 stars2 months ago
We absolutely loved our stay at this villa—it was one of the most luxurious and beautiful places I’ve been. The moment you arrive, you’re greeted with stunning views and an incredible infinity pool that feels like it blends right into the horizon. Every room opens directly onto the pool, which makes the whole space feel open, airy, and seamlessly connected to the outdoors. The villa itself is spacious, with large, comfortable bedrooms and en-suite bathrooms with a walk-in closet and a stylish lounge area that’s perfect for relaxing. Every amenity you could need is thoughtfully provided, making it feel like a true home away from home. Outside, the lush garden adds a peaceful, tropical vibe, and the private parking is a great bonus. Our host, Dmitri and local guide Greg, were excellent—super helpful and responsive throughout the stay. Truly a five-star experience in every way. Will definitely recommend if you are looking for a private getaway.

Luxury villa rentals

Guest favourite
Villa in Collectivity of Saint Martin
5 out of 5 average rating, 30 reviews

OOF architect's villa, sea view facing Pinel Island

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 favourite
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!
Guest favourite
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!
Superhost
Villa in Lowlands
4.96 out of 5 average rating, 25 reviews

Reflection Z 5 Star Villa

HeatherRating, 5 stars5 months ago
We really enjoyed our time at this villa perfect location
Guest favourite
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.
Top guest favourite
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 stars16 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.
Guest favourite
Villa in Orient Bay
5 out of 5 average rating, 5 reviews

Beautiful 4 bedroom villa, close to the beach!

WendyRating, 5 stars2 months ago
We enjoyed our stay at this lovely villa. Emma personally greeted us when we arrived and made sure we had everything we needed to begin our vacation. The villa had all of the comforts of home, a well-appointed kitchen (and bonus outdoor kitchen) and a wonderful outdoor space for enjoying coffee, reading a book and letting the kids play in the pool. An easy walk to the beach and restaurants of Orient Bay. We would stay here again!

Villa rentals with a pool

Guest favourite
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.
Guest favourite
Villa in Upper Prince's Quarter
4.78 out of 5 average rating, 63 reviews

Oceanfront Guana Bay Villa with View of St. Barts

NicoleRating, 5 stars1 month ago
A home away from home for an entire week with an incredible view in a serene-peaceful area. It is the perfect place especially for a family or few friends as the layout allows for some retreat space at the end of your day. Kevin’s proactive approach in the villa includes nearly everything you’ll need while staying there. If you’re looking for serenity in an amazing villa with exceptional amenities hosted by a great host- look no further!!!!
Top guest favourite
Villa in Les Terres Basses
5 out of 5 average rating, 27 reviews

Brand new! - Slowlife - Enjoy Villa

JonathanRating, 5 stars4 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!
Superhost
Villa in Orient Bay
4.85 out of 5 average rating, 66 reviews

Villa BO Beach, private pool, 2+1 bedrooms

EstelleRating, 5 stars3 weeks ago
Very nice house. 2 min walk to the sea and shops
Guest favourite
Villa in Collectivité de Saint-Martin
5 out of 5 average rating, 8 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 favourite
Villa in Residence Hope Hill
4.97 out of 5 average rating, 31 reviews

Villa Azur, great view of the Orient Bay

IdaraesitRating, 5 stars3 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

    $192 SGD 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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