
House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Simpson Bay house rentals
House rentals with a pool

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
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!!

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.

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!!!

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!!!

Luxurious Villa "Sea La Vie"
Amazing spot on an amazing Island!

"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 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! :)
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!

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!

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

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!!

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.

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!

4 Clos de l'Anse - Anse Marcel
Julie’s place is a great spot in a quiet location near Anse Marcel beach. We loved the outdoor space and enjoyed cooling off in the pool.
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.

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 view of St Barth – 8 people
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.

Villa Prospère
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.

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
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!
Quick stats about house rentals in Simpson Bay
Total rentals
20 properties
Nightly prices starting at
G$12,589 GYD 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 Vacation rentals
- Marigot Vacation rentals
- Philipsburg Vacation rentals
- Gustavia Vacation rentals
- Cul-de-Sac Vacation rentals
- Bakers Bay Vacation rentals
- Cole Bay Vacation rentals
- Anse Marcel Vacation rentals
- Les Terres Basses Vacation rentals
- Anegada Vacation rentals
- Basseterre Vacation rentals
- San Juan Vacation rentals
- Rentals with a washer and dryer Simpson Bay
- Kid-friendly rentals Simpson Bay
- Pet-friendly rentals Simpson Bay
- Beach condo rentals Simpson Bay
- Rentals with a hot tub Simpson Bay
- Condo rentals Simpson Bay
- Rentals with a patio Simpson Bay
- Serviced apartment rentals Simpson Bay
- Rentals with pools Simpson Bay
- Apartment rentals Simpson Bay
- Fitness-friendly rentals Simpson Bay
- Smoking-friendly rentals Simpson Bay
- Beachfront rentals Simpson Bay
- Family-friendly rentals Simpson Bay
- Rentals with beach access Simpson Bay
- Rentals with outdoor seating Simpson Bay
- Rentals with breakfast Simpson Bay
- Waterfront rentals Simpson Bay
- Villa rentals Simpson Bay
- House rentals Sint Maarten
- 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