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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

Superhost
Home in Oyster Pond
5 out of 5 average rating, 4 reviews

Le Spot - Unique house with view

SaskiaRating, 5 stars3 months ago
Apartment with fantastic views. You look all around over St Maarten and the sea. Apartment was very fully equipped, dishwasher and washing machine available. There were also new bath towels ready. Everything looked taken care of. Definitely recommended!
Guest favourite
Home in Little Bay
4.95 out of 5 average rating, 81 reviews

Villa Kailani 4 bedroom with Stunning Ocean Views

BillRating, 5 stars4 months ago
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.
Superhost
Home in Cul-de-Sac
4.88 out of 5 average rating, 17 reviews

Maison Ti Case, private pool, near Pinel Island

AurélieRating, 5 stars3 weeks ago
The accommodation is even better than in the photos, the place is peaceful and close to Grand-Case airport. Gilles was very responsive and friendly, we will recommend to our friends, thank you for the responsiveness!
Guest favourite
Home in Collectivity of Saint Martin
4.88 out of 5 average rating, 77 reviews

ALMOND BLUE ...Pinel bay view - caribbean feeling

JoelRating, 5 stars2 months ago
Villa Almond Blue enjoys an extraordinary view, sublime facing the bay. You can see Pinel and Saint Barth from the terrace, installed in a pleasant covered outdoor lounge The house, very nice and simple to live in, offers all the essentials to spend pleasant moments of relaxation.
Superhost
Home in Cole Bay
4.86 out of 5 average rating, 29 reviews

Luxury, Villa Panoramic Sea Views, Pelican Key

EphraimRating, 5 stars13 months ago
We had an amazing time staying in Mike's home. The house itself is clean, safe, and a perfect place to relax in the pool with a view. Michael was a great communicator leading up to the trip and gave us fantastic recommendations. Once we arrived, Peaches was there for us in everyway, constantly responsive to our questions and even picked up a lost item from a taxi for us! My biggest recommendation if you stay here is to rent a car, the house is a bit further back in a neighborhood ( makes for a nice and quiet area) but pretty difficult if you would like to walk anywhere. There are restaurants and bars just a few minutes away a long with a number of grocery stores. Driving to both Marigot and Phillipsburg only took around 15-20 minutes depending on traffic, so the house was in a great location to get around the island. Would absolutely stay there again.
Guest favourite
Home in Blowing Point
5 out of 5 average rating, 7 reviews

Newly Renovated 2 Bedroom Villa

MarianneRating, 5 stars4 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!!!
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 stars3 months 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 in Philipsburg
4.95 out of 5 average rating, 58 reviews

Villa Allamanda a Indigo Bay

AlenaRating, 5 stars3 months ago
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

Guest favourite
Home in Upper Prince's Quarter
4.86 out of 5 average rating, 35 reviews

Peaceful secluded 2BR apt w. sunrise & ocean views

KimberlyRating, 5 stars1 month ago
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!
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 stars3 months 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!
Top guest favourite
Home in Collectivité de Saint-Martin
4.95 out of 5 average rating, 22 reviews

Villa close to the beach

MeagenRating, 5 stars1 month ago
My family and I have stayed at dozens of rental homes all over the world. This was the absolute best experience we have ever had. First things first, the house is CLEAN. So very clean and modern. The beds are comfortable with lovely linens and good quality pillows. The bathrooms are spa-like with great water pressure and plenty of hot water. The kitchen is a dream! Fully stocked with great quality appliances and tools. The pool was crystal clear the entire week. The backyard is an absolute oasis. There are houses all around, but the backyard is so private. The owners did a wonderful job with trees and flowering bushes. You're just a short stroll from the gorgeous beach. The beach clubs, water sports and restaurants are excellent! My teen daughters loved the pool area, upstairs deck (with charming swing!) and beautiful beach to take all of their hundreds of photos! The best part of renting this house is the wonderful Laurette! She made us all feel like VIP guests! 10 Stars!
Superhost
Home in Cole Bay
4.88 out of 5 average rating, 8 reviews

Casalinda Amazing Sunsets Pelican Key St Maarten

EmmaRating, 5 stars3 months ago
absolutely amazing! gorgeous views, very clean, host is super super nice and helpful would 10/10 recommend!
Guest favourite
Home in Grandes Cayes
4.89 out of 5 average rating, 28 reviews

Red Rock Villa: 3 bedrooms & private pool

Peter N.Rating, 5 stars2 months 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 MF
4.92 out of 5 average rating, 37 reviews

Villa Tukan, Baie Orientale Village

MitchellRating, 5 stars3 months ago
Beautiful location walk to lots of restaurants seconds from the beach walking. Private yard great pool quiet. Couldn’t have been happier.
Guest favourite
Home in Upper Prince's Quarter
4.97 out of 5 average rating, 70 reviews

Villa Tamarind | Luxury Oasis | Ocean views | 4BDR

JasonRating, 5 stars1 month ago
Even better the 2nd time around. Vincent and team are great - communication is excellent. Couldn’t ask for a better place to spend a week!
Guest favourite
Home in Lowlands
5 out of 5 average rating, 16 reviews

Modern artist's villa

MickeyRating, 5 stars3 weeks ago
I really recommend this home for a stay in St. Martin. My driver had little trouble locating it because of the direction we took but that was resolved quickly. Very clean, comfortable, had everything I needed & more. From laundry, to dishes, to beach supplies. It's in the perfect location in Maho. I felt @ home. I'd stay here again! What ever questions or concerns I had Mario & his team responded quickly. Only con I will add is the king bed (master) is 2 twin mattresses... I kept falling between the mattresses which was annoying, along with my shower not having hot water after midnight. But the other shower was fine.

Private house rentals

Home in Lowlands
4.86 out of 5 average rating, 77 reviews

Sapphire Fantasy : Oceanfront paradise

ShavonaRating, 5 stars2 months ago
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.
Guest favourite
Home in Cole Bay
5 out of 5 average rating, 12 reviews

Pelican key - BEACH FRONT Villa

JohnnyRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Simpson Bay
5 out of 5 average rating, 14 reviews

Beach cottage in Simpson bay

BriannaRating, 5 stars1 month ago
Had a great stay! Location is amazing we are so grateful for this beautiful property to make our trip truly memorable!
Top guest favourite
Home in Upper Prince's Quarter
5 out of 5 average rating, 6 reviews

Breathtaking views of St Barth - 8 people

DennishaRating, 5 stars6 days ago
Truly a dream stay with an incredible ocean view. We had the most incredible experience staying at this stunning property! From the moment we arrived, we were blown away by the breathtaking panorama, crystal-clear waters. The home itself was spotless, stylishly decorated, and equipped with every comfort we could ask for. Waking up to the sound of the waves each morning was pure magic. The location was also perfect, peaceful and private, yet just a short drive to local shops, restaurants, and coastal attractions. Our hosts went above and beyond, they even helped us book dinner reservations when we didn’t have international phone service, which made a huge difference in our trip. It’s clear they genuinely care about providing a top-tier guest experience. We didn’t want to leave and are already planning our return. If you're looking for a relaxing, scenic getaway by the sea, this is it. Highly, highly recommend!
Guest favourite
Home in Simpson Bay
4.92 out of 5 average rating, 12 reviews

Coco's Beach House - Simpson Bay Beach

ClydeRating, 5 stars3 months ago
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.
Home in Indigo Bay
4.77 out of 5 average rating, 157 reviews

La Pearle - Luxurious 1 Bedroom Condo By the Beach

ShandraRating, 5 stars1 week ago
Le Pearle, is an amazing place to stay while in paradise. The location is private, the views are incredible, and you have the luxury of a beach at your disposable. The condo itself is very beautiful, the bed is comfortable, my boyfriend and I felt right at home and would highly recommend staying here.
Top guest favourite
Home in Cul-de-Sac
4.93 out of 5 average rating, 69 reviews

C’est la Vie! Private pool and amazing views !

BenjaminRating, 5 stars1 month ago
Isabelle’s property came even better than advertised and Isabelle was a very gracious hostess from pre-arrival throughout our stay. Incredible views of the bay in the evening, and can even see St Barth in the distance when clear. The property had all the comforts of home (US) with the charm of St. Martin. I sent Isabelle a couple of messages for local recommendations during our visit and she was quick and helpful with her responses. Merci beaucoup for a wonderful stay!!
Top guest favourite
Home in Upper Prince's Quarter
5 out of 5 average rating, 6 reviews

Aman Oceanview

KeeshaRating, 5 stars3 weeks ago
Irene was such a great host, she was very helpful and friendly. Greeted us with champagne and made us feel at home in the luxurious property. She had a handful of resources for our stay and was readily available for questions. I plan on coming back to the property. The views were absolutely stunning.

Quick stats about house rentals in Simpson Bay

  • Total rentals

    20 properties

  • Nightly prices starting at

    $77 SGD 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

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