
House holiday rentals in Simpson Bay
Find and book unique houses on Airbnb
Top-rated house rentals in Simpson Bay
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Simpson Bay
House rentals with a pool

Villa Taïana - Oyster Pond
We had an amazing weekend Best villa I had ever rented I loved it Will b renting it again. The host was super nice easy to contact VERY VERY nice Everything was just amazing I’m very satisfied 🙏🏾

Villa Vijoux Luxury, Modern OceanView 8 Bedrooms
I recently had the pleasure of staying at Villa Vijoux in Saint Maarten, and I can confidently say it was one of the most unforgettable experiences of my life. From the moment we arrived, we were greeted with warm hospitality and breathtaking views that set the tone for our entire stay. The villa itself is a stunning blend of luxury and comfort. Spacious and beautifully decorated, it features modern amenities that made our stay incredibly enjoyable. The open-concept living area seamlessly flows into the outdoor terrace, where we spent countless hours soaking up the sun and enjoying the panoramic ocean views. The infinity pool was a highlight, providing the perfect spot to unwind with a cocktail in hand while watching the sunset. The location of Villa Vijoux is ideal for exploring the best of Saint Maarten. Nestled in a peaceful neighborhood. What truly sets Villa Vijoux apart is the exceptional service provided by the hosts. They went above and beyond to ensure we had everything.

Slowlife - Villa Wellness 4 beds
Amazing villa close to everything on the Island! We loved the short drive to Mullet Beach and back! Villa outdoor space is incredible and we loved the pool! Enough space for everyone, and a lovely host + daily cleaning! Would highly recommend this villa!

Pelican Paradise
Perfect little villa (actually much bigger than we expected), located in the best neighbourhood of St-Maarten, and managed by a true Superhost!

Villa Louisiana
Highly recommend staying here.

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

Maison les Sucriers, Baie Orientale le Village
We had a very nice stay. The location of the house is fantastic and is close to all restaurants, beach grocery store. The host was very flexible when we arrived and we are very grateful for that . The place was very clean and well maintained. We'll definitely be back! Thank you!

3 Bedroom Ocean Front Villa, Private Infinity Pool
Ideal location for a family vacation with friends. Michelle was very responsive and made us feel at home!
Weekly house rentals

Villa Galapagos, 3 Bedroom, Orient Bay Beach
This was our 2nd stay at Villa Galapagos and was even better than our stay last year. The new outdoor table and chairs are a huge improvement and is an ideal dining space. The new SXM beach towels were a nice addition. You can check my prior review which includes info on the bedrooms, bathrooms, kitchen and outdoor cooking facilities. Those were all outstanding as they were last year. Philippe is responsive when a question comes up. Check in is super simple. We highly this Villa

Sea La’Vie — 2mins walk from the beach!
Our stay here was amazing. Location was 10 minutes from the airport. Walking distance from sunset beach bar and restaurants. Beach access right in the back of the Airbnb. Walking distance away from the market. We walked there every morning to eat Johnny cakes before going out for the day. Lateefa recommended a taxi in which we used the whole trip. We felt very safe. Great place to stay.

Blue Horizon villa
My wife and I spent a lovely nine days at Olivier’s hillside villa. We thoroughly enjoyed the beautiful views and quaint surroundings. Olivier was always immediately responsive to any questions we had. We look forward to returning again soon.

Prestigious Villa with Breathtaking Ocean View
Many Great things to say about Marion's home and about Marion. Marion greeted us at the house for check in and walked us through all we would need to know or possibly use at the house during our stay. Additionally, she had specifically helped me with some excellent restaurant and beach suggestions during. The views, the pool and outside area are all as described and absolutely gorgeous. The house in modern and beautifully decorated. The kitchen is a spacious, well-appointed centerpoint of the home and has everything you would need from a simple, to complex meal setup up for a group. But more importantly Marion is a just a wonderful friendly person and we enjoyed talking to her and really appreciated her sharing her background and history in St. Maarten. Excellent stay - 5 Stars!

Villa Zen: comfort and luxury view of St Martin sea view
Beautiful property with a wonderful view. Very private but only a quick drive from the beach, restaurants, grocery store, etc. You’ll have everything you need for a comfortable stay at this villa. Would highly recommend to anyone considering a stay here.

Villa Caribbean Star, 5 min walk to the beach
We stayed here with two families for a week in July. Having been to Orient twice before we had a very good feel for the area and amenities. The location of Caribbean Star was great to be able to walk to the beach or the many restaurants and bars nearby in the villlage. The house itself was very clean and as described. It worked very well for two couples in the master and basement while the kids had two bedrooms to share. The outdoor area was very nice with a newer pool and great patio space to enjoy the evening. Overall The hosts were very helpful, responsive and genuine in helping us have a good time. We would definitely consider going back in our next visit to the island!

Coconut Beach Villa Sxm
Great location, close to several beaches in walking distance. Close to Grand Case with it's restaurants in walking distance. Nice villa, good swimming pool, spacey garden. View on the green mountains. Easy to check-in and check-out. Clear instructions.

Ocean view villa at Dawn beach
Our second time at this villa and we are already planning our next visit ! Just can get enough of the view!!! Dmitri is amazing host, very helpful and responsive. And his stuff on site Greg is great! We arrived late due to flight delayed and asked for food delivery service recommendations, and Greg offered us to deliver food from his restaurant right to our arrival. It’s was very nice and delicious we appreciated it since been very tired and did not want to go anywhere. Just not enough space here to describe how great this place is. I’m an Airbnb host myself and very picky when it comes to guests service and cleanliness of the place. Both got my A++++ . Thank you again for hosting us!!!
Private house rentals

Pelican key - BEACH FRONT Villa
Alexandra's place was beautiful... The inside space was great but the outdoor space was absolutely amazing! It is nice an quite, great view of the ocean and the ships and boats coming and going... It was quite windy while we were there so we were not able to swim in the ocean but loved the pool!

Nice Villa for 6 Orient Bay Beach
You couldn’t ask for a better location. It’s steps away from some of the best beach bars in Orient Bay. The house has a lovely deck on the 2nd floor with great views of the water and hills. Very peaceful. And there were some very thoughtful welcome amenities provided at checkin. Overall a great stay.

Villa Prospère
Great location, close to Maho beach. Walkable to many attractions Jusnel is very responsive and always available for questions. Would definitely stay there again on our next trip.

NEW House 2 bathrooms, 3 terraces and ocean view
We had a wonderful time staying in Laurent’s apartment/home. It is clean, bright, and a good size for 4 people. The neighborhood is safe and quiet. It is close to area beaches and restaurants in Grand Case, Orient Bay, and other locations. We found Laurent very responsive to questions we had while there.

Casa Coral, Sint Maarten
Shelby was very attentive to our needs. Water is not hot but that apparently is what the island has. Water pressure is not the greatest but did the job. Being beside the airport was very convenient but not quiet. We all had a great trip and appreciate Shelby a lot.

Caribbean Style Family Home
Judy’s home provides an authentic Caribbean experience. The home is spacious, has good amenities and comfortable. My family felt right at home and had a wonderful stay.

Very pleasant ocean view house with swimming pool
Thierry’s house was perfect, clean, beautifully decorated, lovely outside space, we loved the little pool ….. it was just perfect, the photos don’t do it justice. Colette who met us was lovely too and very helpful We would return in a heartbeat!!

Red Rock Villa - 3 Bedroom Private Pool
I visited Julie's with my parents, my wife, and my two young boys and we had a great time. There was plenty of space for us to relax between outings to the beach and activities. The beds were some of the more comfortable we've had at any airbnb. It's in a great location very near Anse Marcel and Pinel, and also close to Orient, Grand Case, and the Super U and Express. The unit is clean and well kept. The pool was also very clean and the got even got cleaned once while we stayed - the pool is slightly on the smaller side, but still plenty big enough for my family. The only slight negatives for our stay would be the lack of a view from the unit(not a big deal) and the hot water was limited (easily worked around by taking shorter showers). We would definitely stay at Julie's place again and would highly recommend it.
Quick stats about house rentals in Simpson Bay
Total rentals
20 properties
Nightly prices starting at
£47 before taxes and fees
Total number of reviews
530 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
- Gustavia Holiday rentals
- Cul-de-Sac Holiday rentals
- Cole Bay Holiday rentals
- Anse Marcel Holiday rentals
- Bakers Bay Holiday rentals
- Les Terres Basses Holiday rentals
- Anegada Holiday rentals
- Basseterre Holiday rentals
- San Juan Holiday rentals
- Guest house rentals Saint Martin
- House rentals Saint Martin
- Beach house rentals Sint Maarten
- Guest house rentals Sint Maarten
- House rentals Sint Maarten
- House rentals Saint Barthélemy
- Family-friendly rentals Simpson Bay
- Monthly Rentals Simpson Bay
- Beach apartment rentals Simpson Bay
- Rentals with pools Simpson Bay
- Rentals with a hot tub Simpson Bay
- Family-friendly rentals Simpson Bay
- Pet-friendly rentals Simpson Bay
- Rentals with a washing machine and dryer Simpson Bay
- Flat rentals Simpson Bay
- Beachfront rentals Simpson Bay
- Waterfront rentals Simpson Bay
- Villa rentals Simpson Bay
- Rentals with a patio Simpson Bay
- Apartment rentals Simpson Bay
- Fitness-friendly rentals Simpson Bay
- Smoking-friendly rentals Simpson Bay
- Rentals with beach access Simpson Bay
- Serviced apartment rentals Simpson Bay
- Rentals with outdoor seating Simpson Bay
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom