House holiday rentals in Simpson Bay

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.

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

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.

We had a fantastic time at Marion's house! She was amazing! The location is great - gated community between Grand Case and Marigot and not far from Orient Beach. The house was very clean and had everything we needed. View was amazing, pool and patio were nice (we spent a lot of time on the outdoor furniture), all the beds were super comfortable and the kitchen was very well equipped! Marion had some excellent dinner suggestions (even made our reservation for us at one place that was hard to get in) and she has a hook up with one of the beach restaurants at Orient that got us free chairs for the day. It might be worth noting that the house is a part of a 4-5 unit complex with neighbors on each side and a rental unit down below. However, this was not an issue as we rarely heard any of the neighbors and there is plenty of shrubbery and other elements that give adequate privacy. We even had a couples massage on the patio one day! Overall very pleased and highly recommend!!!

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!!!

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.

Our stay was amazing! Props to the property manager, he was always there to help and responded super quick to any questions or concerns. Place was beautiful, although the pool was tiny it wasn't a huge deal. Only downside was that, during our stay, a mirror fell off the wall in the middle of the night and slightly shattered due to no fault of our own. My guess is it was hanging on something that broke... we were still asked to pay for the damages even though it was on them to better secure it to the wall. Other than that, great place and host! :)

This is a remarkable home and location. We could have stayed all day and soaked up the sun and views on the patio and in the lounge pool. The location is great to explore the island from. It is also quiet and peaceful. We decided to stay in the upper side of the island so getting to Orient Bay and Grand Case was a breeze. The home is within 15-20 minutes by car to some of the best restaurants we’ve ever been to. There’s also a great cafe within 10 minutes for coffee and pastries. Maia was very helpful and also taking advantage of the property concierge was very nice to get our trip started and help line up a few things for us. With two young children this was so perfect and the best vacation we’ve ever had!

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!

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!

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!

Enjoyed a great Christmas and New Year’s stay at Villa Palm Dove. The home is situated up on a hill in a quiet and very secure neighborhood with a great view and cool ocean breezes. It has a well appointed kitchen with everything you’d need for a few meals at home. Bathrooms are spacious and the outside shower was a nice touch. The pool and outside lounge spaces were comfortable and inviting. A nice “extra” is that this home has satellite television with an extraordinary amount of channels to catch US sports or streaming shows. The management team was very helpful and communicated well for arrivals and departures. Also very attentive and checking in throughout the stay. All in all, great spot and we’ll keep it on our short list for future stays.

Absolutely beautiful villa! The photos don’t do the place justice. The home is gorgeously decorated. The kitchen is stunning and well stocked. The pool was spotless and perfect to cool down after a day out. There were between 8 and 9 of us and we never felt crowded! Virginie was also an incredible host, always responsive and so helpful with any questions we had. I couldn’t recommend more!

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.

AMAZING! This property exceeded out expectations. From the moment we walked on the property we felt like we were in paradise. From the landscaping to the interior, everything was so well done and thought out. The views from this property were simply breathtaking. Taking the kayaks over to Pinel Island was so much fun and very easy. The pool was a wonderful way to start and end our days and was extremely well maintained. Melissa was our concierge for our trip and from the moment we started planning to the day we checked out she was fabulous to work with. All of our groceries were there when we showed up, we had reservations that she made for us at a new beach each day, and dinner reservations were also made by her for each night, this made out days flow seamlessly. If we needed anything or if there were any changes we wanted to make she was extremely prompt and helpful with her responses. We would love to go back and do it all again!

Lovely place, totally worth it. Would definitely come back.

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.

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.

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

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!

The host was incredibly responsive and kind. The pool was amazing, and we thoroughly enjoyed our stay. It was within walking distance to the beach and restaurants, and only an 8-minute drive from the airport.

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!

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.

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.