
House vacation rentals in Simpson Bay
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Top-rated house rentals in Simpson Bay
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Popular amenities for Simpson Bay house rentals
House rentals with a pool

Le Spot - Unique house with view
Apartment with fantastic views. You look all around over St Maarten and the sea. Apartment was very fully equipped, dishwasher and washing machine available. There were also new bath towels ready. Everything looked taken care of. Definitely recommended!

Villa Kailani 4 bedroom with Stunning Ocean Views
Awesome home with a relaxing feel, unbelievable views and very comfortable setting for 8 people. This is our second stay and can’t wait to come back again. Every bedroom has a picturesque view and sunrises are beautiful. There is ample room for everyone with multiple outdoor seating areas and a huge pool deck. Maayke is a great host who was super helpful and very quick to respond to questions. Absolutely recommend this place for an unforgettable vacation.

Maison Ti Case, private pool, near Pinel Island
The accommodation is even better than in the photos, the place is peaceful and close to Grand-Case airport. Gilles was very responsive and friendly, we will recommend to our friends, thank you for the responsiveness!

NEW House 2 bathrooms, 3 terraces and ocean view
Laurent was very helpful and friendly. The property was very nice and secure .

Spacious villa 8 people swimming pool sea view
Hidden gem! Such a beautiful home and thoughtfully put together. We had a child and the house felt so safe even the pool had an alarm if a child fell in. The house has everything you need and more. We will be back again!

ALMOND BLUE ...Pinel bay view - caribbean feeling
Villa Almond Blue enjoys an extraordinary, sublime view facing the bay. You can see Pinel and Saint Barth from the terrace, installed in a pleasant covered outdoor lounge The house, very pleasant and simple to live in, offers all the essentials for pleasant moments of relaxation.

Luxury, Villa Panoramic Sea Views, Pelican Key
We had an amazing time staying in Mike's home. The house itself is clean, safe, and a perfect place to relax in the pool with a view. Michael was a great communicator leading up to the trip and gave us fantastic recommendations. Once we arrived, Peaches was there for us in everyway, constantly responsive to our questions and even picked up a lost item from a taxi for us! My biggest recommendation if you stay here is to rent a car, the house is a bit further back in a neighborhood ( makes for a nice and quiet area) but pretty difficult if you would like to walk anywhere. There are restaurants and bars just a few minutes away a long with a number of grocery stores. Driving to both Marigot and Phillipsburg only took around 15-20 minutes depending on traffic, so the house was in a great location to get around the island. Would absolutely stay there again.

Newly Renovated 2 Bedroom Villa
Aline and Katie were great to work with leading up to our trip. They looked into finding the best place for us to watch the Super Bowl (Go Birds!) and went on a shopping hunt to look for a thermos for the beach for us. Eli made our trip great!! He met us at the airport, led us to the villa, showed us around and had a welcome snack and beverage awaiting our arrival as well as the shopping list of groceries we asked for. Eli also arranged for us to get a Firestick to watch the Super Bowl in the comfort of our villa to watch the Eagles win! He checked in on us multiple times during our 9 night stay. The pool was the warmest of any we have rented in the Caribbean. The rooms were spacious and clean. Our only critique was that showers needed to be spaced apart for 4 people due to lack of hot water but it was manageable. Great stay!!!
Weekly house rentals

Peaceful secluded 2BR apt w. sunrise & ocean views
Adventurous and romantic! Exactly what we are looking for! It felt private despite the convenience of having the host nearby. Melissa was wonderful and very helpful. We sat on the patio and watched boats and cars and birds galore! There are some critters on the cliffs, like iguanas, but they won’t bother you. The breeze and air felt wonderful and I loved listening to the waves at night. I am very happy to chose to rent a Suzuki Jimny, as we observed other vehicles without 4x4 getting stuck on some nearby roads. It was exciting to see our cliff AirBnB from the catamaran tour we took. A lot of excursions go out of Bobby’s Marina, which is conveniently nearby and has secure parking for day trips. Trust the journey, the destination is beyond worth it!

Villa close to the beach
My family and I have stayed at dozens of rental homes all over the world. This was the absolute best experience we have ever had. First things first, the house is CLEAN. So very clean and modern. The beds are comfortable with lovely linens and good quality pillows. The bathrooms are spa-like with great water pressure and plenty of hot water. The kitchen is a dream! Fully stocked with great quality appliances and tools. The pool was crystal clear the entire week. The backyard is an absolute oasis. There are houses all around, but the backyard is so private. The owners did a wonderful job with trees and flowering bushes. You're just a short stroll from the gorgeous beach. The beach clubs, water sports and restaurants are excellent! My teen daughters loved the pool area, upstairs deck (with charming swing!) and beautiful beach to take all of their hundreds of photos! The best part of renting this house is the wonderful Laurette! She made us all feel like VIP guests! 10 Stars!

3-Bedroom Home In Philipsburg, Near the Beach
Our stay at Cheryl's spacious Airbnb was an excellent experience. The house and its amenities exceeded our expectations. Especially the kitchen was equipped with everything needed and more. We traveled with children and Cheryl's house had some toys and children's beach equipment. The house is located very central in Philipsburg, in one of its busier areas. The beach was right across the street from the house. Cheryl was very attentive and responsive at all times and made us feel very welcomed and safe in her house. We would choose to stay at her house again without a doubt.

Red Rock Villa: 3 bedrooms & private pool
Spectacular home. Private, quiet, yet minutes away from beaches and quality restaurants. Checking in and out was well coordinated by the team, as were responses to queries. A wonderful stay, highly recommended.

Villa Tukan, Baie Orientale Village
Beautiful location walk to lots of restaurants seconds from the beach walking. Private yard great pool quiet. Couldn’t have been happier.

"La Vue SXM" Paradise "Villa Rosa" 5 bedroom rate
Our stay for 8 people was wonderful. The area is more beautiful than imagined, and the pictures surely do not do it justice. The house is very private, and you need to traverse a couple large hills in order to get there. We had to swap out our first rental car because the tread felt very unsafe and struggled on some of the hills, but otherwise we really appreciated the privacy and sweeping views of the water from the villa.

Villa Tamarind | Luxury Oasis | Ocean views | 4BDR
Even better the 2nd time around. Vincent and team are great - communication is excellent. Couldn’t ask for a better place to spend a week!

Modern artist's villa
I really recommend this home for a stay in St. Martin. My driver had little trouble locating it because of the direction we took but that was resolved quickly. Very clean, comfortable, had everything I needed & more. From laundry, to dishes, to beach supplies. It's in the perfect location in Maho. I felt @ home. I'd stay here again! What ever questions or concerns I had Mario & his team responded quickly. Only con I will add is the king bed (master) is 2 twin mattresses... I kept falling between the mattresses which was annoying, along with my shower not having hot water after midnight. But the other shower was fine.
Private house rentals

Sapphire Fantasy : Oceanfront paradise
My stay at Smaart Vacation exceeded my expectations. Everything was as it was described on the booking site. The view was breathtaking! The property was in the perfect location. It was a lot to do in the area. I will book with them again in the near future. Look no further for a perfect stay in SXM.

Pelican key - BEACH FRONT Villa
Alex’s place was great, it had a small private beach albeit a bit rocky. For adults that is good. For kids, there is a pool for them to play in. I would assume when the waves are a bit more calm it would be good for the kids to go in. Her house is also stocked with lots of kids toys so we were able to keep all the kids entertained while the adults lounge around. The one complaint I have is designated parking spots, the area has an abundance of street parking, but a few dedicated spots for the house would be nice. However this is not an issue with the house itself.

Beach cottage in Simpson bay
Had a great stay! Location is amazing we are so grateful for this beautiful property to make our trip truly memorable!

Breathtaking view of St Barth – 8 people
Truly a dream stay with an incredible ocean view. We had the most incredible experience staying at this stunning property! From the moment we arrived, we were blown away by the breathtaking panorama, crystal-clear waters. The home itself was spotless, stylishly decorated, and equipped with every comfort we could ask for. Waking up to the sound of the waves each morning was pure magic. The location was also perfect, peaceful and private, yet just a short drive to local shops, restaurants, and coastal attractions. Our hosts went above and beyond, they even helped us book dinner reservations when we didn’t have international phone service, which made a huge difference in our trip. It’s clear they genuinely care about providing a top-tier guest experience. We didn’t want to leave and are already planning our return. If you're looking for a relaxing, scenic getaway by the sea, this is it. Highly, highly recommend!

Peaceful Paradise
Clark’s place was beautiful. It was spotless, modern, beautifully decorated, and well stocked with all the extras. There were four of us and we had lots of space. The beds were extremely comfortable and each room had its own bathroom. The grounds were stunning, with a pool and direct access to the ocean. Our favorite place was Clark’s deck that had the most incredible views of the gardens and ocean. We could have stayed there all day and night watching the boats, and the ever changing skyline, and sunsets. The location was very central and in a great area. It was within a few blocks (about 5-15 minute walk) to beaches, fun cafes, restaurants, and shops. It was an easy drive to main attractions on the island (e.g., Maho Beach, Orient Bay). Clark was an excellent host - very responsive and answered any questions that we had. We all loved our stay and would highly recommend it!

Coco's Beach House - Simpson Bay Beach
Really enjoyed the stay at this beautiful home. Peaceful love the sound of the ocean at night. Fun to watch the airplanes come by after landing and tiring around. The beach is beautiful and the privacy is second to none.

La Pearle - Luxurious 1 Bedroom Condo By the Beach
Le Pearle, is an amazing place to stay while in paradise. The location is private, the views are incredible, and you have the luxury of a beach at your disposable. The condo itself is very beautiful, the bed is comfortable, my boyfriend and I felt right at home and would highly recommend staying here.

C’est la Vie! Private pool and amazing views !
Isabelle’s property came even better than advertised and Isabelle was a very gracious hostess from pre-arrival throughout our stay. Incredible views of the bay in the evening, and can even see St Barth in the distance when clear. The property had all the comforts of home (US) with the charm of St. Martin. I sent Isabelle a couple of messages for local recommendations during our visit and she was quick and helpful with her responses. Merci beaucoup for a wonderful stay!!
Quick stats about house rentals in Simpson Bay
Total rentals
20 properties
Nightly prices starting at
R1,077 ZAR before taxes and fees
Total number of reviews
600 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Wifi availability
20 properties include access to wifi
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