
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

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 🙏🏾

Beautiful 4BD Villa
We had a great time! The villa is superb, very spacious, a really idyllic and peaceful living environment, rest, idleness. But also nearby festive evening outings at the top!! Very good restaurants at a reasonable price, try the "Lolos" (typical Creole cuisine restaurants) hearty and cheap! Boat trips to the islands (Pinel, Anguilla etc...) are magical, white sand and turquoise water. Our hostesses, Valerie and Sarah are great. Sarah is very responsive, rare kindness, good advice and care should you need anything! We recommend Villa Little Key 100%. Thank you so much Sarah! See you soon! The AZAÏS Family

Villa Vijoux Luxury, Modern OceanView 8 Bedrooms
Absolutely Amazing Stay – One of the Best Airbnbs Ever! Our stay at this Airbnb in St. Martin was nothing short of incredible! From the moment we arrived, we felt welcomed and at home. The host was absolutely amazing—super responsive, incredibly helpful, and went above and beyond to provide us with the best recommendations for restaurants, beaches, and activities. The property itself was stunning—clean, well-equipped, and perfectly located for exploring the island. Every detail was thoughtfully taken care of, making our stay seamless and stress-free. St. Martin has officially become one of my favorite destinations, and a huge part of that is because of how perfect this Airbnb experience was. We are definitely coming back, and I wouldn’t hesitate to book this place again. Highly, highly recommend!

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
This place was amazing. It was exactly as it was described. We had anywhere from 2-8 of us at a time and there was plenty of space and bathrooms also worked out great. We would go back here 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

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!
Weekly house rentals

Sea La’Vie — 2mins walk from the beach!
The place was beautiful, clean and exactly as described. Walkable distance to popular places like D’s bar, sunset bar and maho beach. Lateefah was very communicative and an amazing host. 10/10 would definitely recommend.

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.

Red Rock Villa: 3 bedrooms & 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.

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!!!

Villa Tamarind | Luxury Oasis | Ocean views | 4BDR
We really enjoyed the outdoor space including the pool, bbq, pizza oven and smoker. The view of the ocean and St Barts was absolutely incredible! The warm Caribbean breeze was lovely. The air conditioning in the bedrooms was excellent and the indoor spaces were very roomy. We can hardly wait to come back!

2 Bedroom Ocean Front Villa, Private Infinity Pool
Michelle was an incredible host! She met us upon arrival and made sure we were comfortable and knew all the ins and outs of the villa. The place was exactly as pictured—absolutely gorgeous, with a breathtaking view! She had placed a very thoughtful gift basket out for us, along with recommendations for dining, shopping etc. The home was immaculate…and very well appointed…perhaps the best Airbnb kitchen setup I’ve seen…every time we thought, “I wonder if they have a….” The answer was yes! You could tell that Michelle is very detail oriented from how thoughtfully laid out everything was. And throughout the stay, they were very friendly and communicative, helping us with any questions we had or just being friendly and gracious hosts. This home is a multi unit villa enclosed by a gate and a wall; so Michelle and her husband live next door, but you would never know they were there—it feels very secluded and peaceful. The location is perfect…close to everything.

Préstige - Luxurious 3 bedroom by the Beach
The best thing about the place is the stunning views. I loved staring out of the big windows and from the expansive patio. It’s in a new development so there is a bit of construction going on, but I really didn’t hear it very much. We did have to drive to get to restaurants, local spots but we enjoyed the privacy, away from the crowds and hustle of the touristy areas. Sharina, Biona, and Elizabeth were very helpful and responsive. Very easy to communicate with. Overall, it was an excellent stay.

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!
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
Located in a quiet neighborhood but walking distance to so many things. The place was perfect for us. Everything was very clean. The pool was so nice to have too! Highly recommend if you don’t want to do a resort stay but are still close to things.

NEW House 2 bathrooms, 3 terraces and ocean view
We had a wonderful stay in Laurent’s home. Travelled with child and it was great for our needs. We all had our own space which was comfortable for all. Location has access to beach with just a short walk, or you’re in driving distance to many of our favorite areas on the island. Easy to get to Grand Case, Dock to Pinel, Orient. It’s a quieter area so nice to return home after days out. I would recommend.

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
Beautiful spacious place and was very clean. Felt homy and secured. Host were really nice and attentive to our needs. A bit hard to find but host offered to met us before hand to show us the place.

3-Bedroom Home In Philipsburg, Near the Beach
Cheryl was a wonderful host. She met us to give us the keys when we arrived and walked us through to answer any questions. She also came when we checked out to take the keys. The house location is perfect. Just a block from the Great Bay, all the restaurants, shopping, beach bars. We had a wonderful time exploring Philipsburg. The house was well equipped and secure with parking if you need it. The only downside was the street noise which is especially loud on Saturday and Sunday nights. But the location is what made it special for us and our guests. We are hoping all four of us can come again in a couple of years and we would rent from Cheryl again.

Very pleasant ocean view house with swimming pool
We had a wonderful stay. The villa is as described. We loved the private courtyard and the pool. I would recommend it 100%. Thank you Thierry for the easy communication and thank you to Colette for hosting us.
Quick stats about house rentals in Simpson Bay
Total rentals
20 properties
Nightly prices starting at
$60 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
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