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House vacation rentals in Simpson Bay

Find and book unique houses on Airbnb

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Popular amenities for Simpson Bay house rentals

House rentals with a pool

Guest favorite
Home in Collectivité de Saint-Martin
5 out of 5 average rating, 5 reviews

Villa Taïana - Oyster Pond

DarineRating, 5 stars6 months ago
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 🙏🏾
Superhost
Home in Cul-de-Sac
5 out of 5 average rating, 3 reviews

Beautiful 4BD Villa

LaureRating, 5 stars1 month ago
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
Top guest favorite
Home in St Maarten
4.97 out of 5 average rating, 61 reviews

Villa Vijoux Luxury, Modern OceanView 8 Bedrooms

SaharaRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Les Terres Basses
5 out of 5 average rating, 8 reviews

Slowlife - Villa Wellness 4 beds

AaronRating, 5 stars3 months ago
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!
Guest favorite
Home in Caribbean
4.89 out of 5 average rating, 53 reviews

Pelican Paradise

PhilippeRating, 5 stars1 month ago
Perfect little villa (actually much bigger than we expected), located in the best neighbourhood of St-Maarten, and managed by a true Superhost!
Superhost
Home in Collectivité de Saint-Martin
4.86 out of 5 average rating, 21 reviews

Villa Louisiana

TeresaRating, 5 stars1 month ago
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.
Superhost
Home in Mont vernon 3
4.67 out of 5 average rating, 3 reviews

Villa Carib sxm piscine.

AshantiRating, 5 stars9 months ago
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
Superhost
Home in Parc de la Baie Orientale
4.8 out of 5 average rating, 10 reviews

Maison les Sucriers, Baie Orientale, Le Village

ChristineRating, 5 stars4 months ago
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

Superhost
Home in Simpson Bay
4.86 out of 5 average rating, 22 reviews

Sea La’Vie — 2mins walk from the beach!

AlrickRating, 5 stars2 days ago
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.
Superhost
Home in Collectivité de Saint-Martin
4.8 out of 5 average rating, 20 reviews

Blue Horizon villa

ClarkRating, 5 stars1 month ago
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.
Guest favorite
Home in Grandes Cayes
4.89 out of 5 average rating, 27 reviews

Red Rock Villa: 3 bedrooms & private pool

Jef and MeganRating, 5 stars1 month ago
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.
Top guest favorite
Home in Collectivité de Saint-Martin
5 out of 5 average rating, 15 reviews

Prestigious Villa with Breathtaking Ocean View

DavidRating, 5 stars3 weeks ago
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!!!
Guest favorite
Home in Upper Prince's Quarter
4.97 out of 5 average rating, 68 reviews

Villa Tamarind | Luxury Oasis | Ocean views | 4BDR

KimberleyRating, 5 stars1 month ago
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!
Top guest favorite
Home in Philipsburg
5 out of 5 average rating, 16 reviews

2 Bedroom Ocean Front Villa, Private Infinity Pool

BillRating, 5 stars1 day ago
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.
Home in Indigo Bay
4.84 out of 5 average rating, 172 reviews

Préstige - Luxurious 3 bedroom by the Beach

JenniferRating, 5 stars6 days ago
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.
Guest favorite
Home in Cul-de-Sac
4.94 out of 5 average rating, 36 reviews

Villa Zen: comfort and luxury, sea view, St Martin

BrianRating, 5 stars1 week ago
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

Guest favorite
Home in Cole Bay
5 out of 5 average rating, 6 reviews

Pelican key - BEACH FRONT Villa

H PRating, 5 stars1 month ago
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!
Home in Orient Beach
4.75 out of 5 average rating, 12 reviews

Nice Villa for 6 Orient Bay Beach

RosioRating, 5 stars27 months ago
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.
Home in Simpson Bay
4.65 out of 5 average rating, 43 reviews

Villa Prospère

MicheleRating, 5 stars2 weeks ago
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.
Superhost
Home in Collectivité de Saint-Martin
4.9 out of 5 average rating, 21 reviews

NEW House 2 bathrooms, 3 terraces and ocean view

LeahRating, 5 stars1 week ago
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.
Home in Simpson Bay
4.8 out of 5 average rating, 10 reviews

Casa Coral, Sint Maarten

NancyRating, 5 stars13 months ago
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.
Superhost
Home in Upper Prince's Quarter
4.96 out of 5 average rating, 45 reviews

Caribbean Style Family Home

MélissaRating, 5 stars2 weeks ago
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.
Top guest favorite
Home in Philipsburg
4.98 out of 5 average rating, 47 reviews

3-Bedroom Home In Philipsburg, Near the Beach

SharonRating, 5 stars1 week ago
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.
Home in Collectivity of Saint Martin
4.79 out of 5 average rating, 39 reviews

Very pleasant ocean view house with swimming pool

RoxaneRating, 5 stars1 month ago
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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