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House holiday rentals in Simpson Bay

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Popular amenities for house rentals in Simpson Bay

House rentals with a pool

Guest favourite
Home
5 out of 5 average rating, 5 reviews

Villa Taïana - Oyster Pond

DarineRating, 5 stars7 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 🙏🏾
Top guest favourite
Home in saint-martin
5 out of 5 average rating, 7 reviews

Spacious villa 8 people swimming pool sea view

ShaylaRating, 5 stars1 month ago
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!
Superhost
Home in Sint Maarten
4.67 out of 5 average rating, 12 reviews

Villa 2 Chambres Indigo Bay

JefferyRating, 5 stars1 month ago
Phadya and Robert's "Oceans 29 " was everything that was advertised, beautiful, clean, contemporary with a great central location and breath taking views !!! Check-in was easy with Phadya describing all the Villa amenities and some ins and outs of the property. We would definitely stay here again and will recommend to future Sint Maarteen visitors!!!
Guest favourite
Home in Les Terres Basses
5 out of 5 average rating, 10 reviews

Slowlife - Villa Wellness 4 beds

JosephRating, 5 stars2 weeks ago
From start to finish, our 7 night stay at the villa was flawless! The villa was spotless, fully stocked, and everything was explained completely when we arrived. The windows on the pool side of the villa can open up almost entirely, which was truly beautiful. We felt very secure and the location was ideal, just a 3 minute drive to Porto Cupecoy and Baie Longue. Our 3 boys really enjoyed the pool and the hot tub was the perfect addition for the parents to relax in while the boys swam. The new pickleball court was a perfect fun addition. Daily housekeeping was such a nice bonus too! We had one minor issue when the power flashed off briefly (common on the French side) and the generator kicked on immediately but one of the breakers didn't fully reset. The host was so quick to respond (we felt bad even bothering her) and the issue was resolved in minutes. We really appreciated how responsive and friendly she was.
Superhost
Home in Collectivité de Saint-Martin
4.87 out of 5 average rating, 23 reviews

Villa Louisiana

AshleyRating, 5 stars2 weeks ago
Great location in Orient Bay! The home was perfect for our group with two toddlers. The hosts were very responsive and helpful…no complaints from us!
Superhost
Home in Mont vernon 3
4.67 out of 5 average rating, 3 reviews

Villa Carib sxm piscine.

AshantiRating, 5 stars10 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
Guest favourite
Home in Blowing Point
5 out of 5 average rating, 7 reviews

Newly Renovated 2 Bedroom Villa

MarianneRating, 5 stars2 months ago
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!!!
Superhost
Home in Parc de la Baie Orientale
4.82 out of 5 average rating, 11 reviews

Maison les Sucriers, Baie Orientale, Le Village

TammyRating, 5 stars4 days ago
We enjoyed our stay at Orient Beach. It was a perfect location.

Weekly house rentals

Superhost
Home in MF
5 out of 5 average rating, 3 reviews

Villa Imagine - Terres-Basses - Amazing View

MartyRating, 5 stars1 week ago
The villa was exactly like the pictures. There agent was waiting for us when we arrived. We had asked him about getting lunch close as we had been traveling since early morning and he offered to pick us up something and had it waiting for us. He was very informative about the villa and services that would happen during our stay. (Cleaning, yard and pool). The view was absolutely breathtaking and the villa was immaculate. Could not ask for nicer accommodations. We would not hesitate to go back again. Booking and payment was super easy!
Superhost
Home in Simpson Bay
4.86 out of 5 average rating, 22 reviews

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

AlrickRating, 5 stars3 weeks 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
4.82 out of 5 average rating, 22 reviews

Blue Horizon villa

VanessaRating, 5 stars1 week ago
We had a wonderful time at Olivier’s Blue Horizon Villa. We loved the privacy and views of the outdoor space and the spacious and comfortable interior with cozy bedrooms and a well-appointed kitchen. We had breakfast at home every day and even cooked a couple dinners in. We had one 11 year old boy who used the pool a lot, including night swims! We went without a car the first day and night and were able to easily walk to local beaches and restaurants but our crew included two women over 80 so we decided to rent a car for the remainder of our stay which allowed us to explore some different locations, beaches, sights and restaurants. The home was a little tricky to find in a cab but Olivier was very responsive and helpful from check-in to check-out. Overall it was an excellent and memorable stay at a very special home.
Top guest favourite
Home in Collectivité de Saint-Martin
5 out of 5 average rating, 15 reviews

Prestigious Villa with Breathtaking Ocean View

DavidRating, 5 stars1 month 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 favourite
Home
4.94 out of 5 average rating, 36 reviews

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

BrianRating, 5 stars1 month 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!
Guest favourite
Home in Orient Bay
5 out of 5 average rating, 10 reviews

Caribbean Star Villa, 5 min walk to the beach

JasminRating, 5 stars1 month ago
We had a fun time with our two families of four. The place is perfectly located close to the beach and restaurants. Plenty of room for everyone.
Superhost
Home in Little Bay
4.71 out of 5 average rating, 7 reviews

Five (5) Bedroom Villa in SXM !

ColbyRating, 5 stars2 months ago
The house was incredibly beautiful with a wonderful location. The host was very helpful and wonderful to work with.
Superhost
Home in Collectivity of Saint Martin
4.91 out of 5 average rating, 95 reviews

Coconut Beach Villa Sxm

MathiasRating, 5 stars2 months ago
Great stay, well equipped and comfortable house. Lydia and Esnard were very responsive. Thanks to them. Mathias and Aurélie

Private house rentals

Guest favourite
Home
5 out of 5 average rating, 8 reviews

Pelican key - BEACH FRONT Villa

NicoleRating, 5 stars3 weeks ago
The house was in a great location, walkable to many restaurants and a beach. The washing machine was not working, and Alexandra had it replaced the next day. I would recommend and I would definitely stay again!
Home
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.
Superhost
Home
4.9 out of 5 average rating, 21 reviews

NEW House 2 bathrooms, 3 terraces and ocean view

LeahRating, 5 stars1 month 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 stars14 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.
Home
5 out of 5 average rating, 4 reviews

Villa Casa Antilla Heated Pool Cistern

BrentRating, 5 stars37 months ago
This home is amazing! Can’t wait to come back next year! Everything you need for an amazingly relaxing stay. Highly recommend!! Very clean, comfortable and walking distance to Orient Beach restaurants, shopping and grocery! Katia is a fantastic host!!
Home
4.79 out of 5 average rating, 39 reviews

Very pleasant ocean view house with swimming pool

RoxaneRating, 5 stars2 months 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.
Guest favourite
Home
4.89 out of 5 average rating, 28 reviews

Red Rock Villa: 3 bedrooms & private pool

Peter N.Rating, 5 stars2 weeks ago
Spectacular home. Private, quiet, yet minutes away from beaches and quality restaurants. Checking in and out was well coordinated by the team, as were responses to queries. A wonderful stay, highly recommended.
Guest favourite
Home in Cul-de-Sac
4.89 out of 5 average rating, 38 reviews

C&S ; Spacious 3 BDR 2.5 BTHR with sea view

JuliaRating, 5 stars1 month ago
Our stay at Chrissy's home was a dream! The house is absolutely gorgeous, well designed, clean, spacious, incredible view, fantastic location- it was the best place we've rented on AirBnB. I cannot recommend this stay enough and would gladly return in a heartbeat. Our time in Saint Martin was phenomenal and a huge part of that was due to this amazing house.

Quick stats about house rentals in Simpson Bay

  • Total rentals

    20 properties

  • Nightly prices starting at

    £45 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