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

ALMOND BLUE ...Pinel bay view - caribbean feeling
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.

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.

Villa Carib sxm piscine.
First, the pictures really don’t do this place justice. Second, Flo was beyond amazing, I would definitely recommend this place to anyone who’s traveling to St.Maarten! Till next time Flo! <3

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!!!

Prestigious Villa with Breathtaking Ocean View
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!!!

"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 Zen: comfort and luxury, sea view, St Martin
Great home in a quiet neighborhood with increadible views of the ocean. Home is well-stocked, including fully-stocked kitchen. The outdoor area is amazing and the beds are super comfortable. Very convenient location for our three favorite beaches---Friar's Bay, Anse Marcel, and Orient! Linda and Gilles and their entire team were very responsive when minor issues arose. We enjoyed our trip very much!

Sunrise & OceanView 3 bedroom Villa with Generator
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!
Weekly house rentals

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!

La Cool & Douce SXM, Orient Bay.
Virginie was the best host and you are paradise. It is the perfect location and had so many restaurants that we walked tomorrow throughout our trip. I would highly recommend!!

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.

Beach Cottage – Terres Basses, Baie Longue
This villa was perfect for us in every way! It was exactly what we wanted and expected. It had the old school charm we were looking for. The furniture and furnishings were lovely and comfortable. Mehdi was a lovely host too and gave us the important local info - groceries, restaurants and more. The kitchen well equipped and had everything we needed to cook meals including an outdoor grill. It was perfect location to go for our long morning walks. We could also walk to the beach or do a short drive depending on what we were taking to the beach that day. It was a great location too. Easy to get anywhere. Marigot had shops, great restaurants, markets and more. We have been coming on and off for 40 years and will definitely be back.

Villa Allamanda a Indigo Bay
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! :)

MAHI-MAHI Logde, private pool, Orient Bay
It was one of the best spaces we ever rented via Airbnb. It is a perfect place for 2 adults, completely isolated and private. Pool a big plus. My wife and I are not a big fans of pools in general, but even we use it. It was close to all local restaurants and 5 min drive to supermarket. We already book it for the next year.

Kansha Wellness Property
Great stay no no worries Very quiet and relaxing 10/10
Private house rentals

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!

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.

Breathtaking views of St Barth - 8 guests
The home is luxurious and beautiful with stunning views and surroundings. The kitchen is fully equipped with everything you need and the space to dine is perfect for a family or group. There are so many sitting areas outside and in. The home is large with all rooms master size and facing the ocean. The decor is simple, classic and elegant! It was so easy to communicate and we had all our needs met. The hosts were amazing.

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!

Maison Ti Case, private pool, near Pinel Island
We had a very nice stay. Everything was clean and tidy. Glad the kitchen is so complete! Wonderful swimming pool. Slept well on the good beds. Private, in a nice and quiet area on Sint Maarten. Neighborhood is closed evening and night with a closed gate, safe 👍 Mr. Gilles always responds quickly and kindly. I said I missed tea towels, they were quickly bought and delivered to us. I definitely recommend this place!!

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
This place was absolutely beautiful! It looked exactly like the pictures! I loved how responsive the host was during my stay! I would definitely stay again!

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
₹5,147 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
Destinations to explore
- Grand Case Holiday rentals
- Marigot Holiday rentals
- Philipsburg Holiday rentals
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