
Family-friendly holiday rentals in Simpson Bay
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Top-rated family-friendly rentals in Simpson Bay
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for Simpson Bay family-friendly rentals
Family-friendly home rentals with a hot tub

The Cliff, Ocean View Luxury units
This is our 2nd time staying at the Cliff and it was everything we remembered and more. the grounds are beautiful and well maintained. Someone is always cleaning or doing some sort of maintenance to the property to keep it pristine! the pool renovation is beautiful and a fantastic spot to watch the sunsets. the beach is easily accessible and virtually private with very little interruptions other than some boats passing by. the pictures dont do this place justice. my husband made use of the spa amenities everyday with the sauna and steam room, indoor pool, outdoor pool and beach -he essentially had a hydrotherapy circuit routine every morning. this apartment itself is well maintained and was exactly as advertised. our favorite spot was on the balcony enjoying the perfect views of the ocean. We have so many spots on the island close by as far as restuarants and two grocery/markets. there are also many rest. in a close drive. when we come back to St Martin, i'm staying here again!

The Cliff in Cupecoy Beach HEAVEN!!!
The communication with Joe and the stay was excellent. The amenities were great and whoever he has doing the housekeeping, does a great job. The concierge at the front desk is like being at a hotel and there’s a restaurant right on site like staying at a four star hotel with having your complete privacy to yourself

FLASH SALE! June-Sept. 2025! Ocean&Tropical Views!
Wonderful location in Simpson Bay. It is walking accessible to everything in the area.

Villa Sunrise - Amazing View of Orient Bay
Excellent place with an amazing view. Great staff.

The Rock 2 Duplex Sea View Apartment with Jacuzzi
Our stay at the Rock was perfect! Such a great location. Florence was super direct and clear with all of the instructions, very quick to respond. Her mom Nicole was so sweet. The perfects hosts. Will hopefully be back one day! Already miss the views.

Top of the art penthouse
Beautiful place on Simpson bay. Perfect location! We were able to walk to many restaurants and Simona helped us with grocery delivery when we arrived, which was very convenient. Make sure to keep doors closed at all times. We briefly left a door open to the balcony and a terrible soiled smell filled the home off and on for a couple days. Home looked just like photos and all amenities were a great addition. Thanks for hosting us!

Beautiful villa Azur ,Low Lands ,private tennis
Great location, host and overall experience.

Le Colibri – Oriental Bay – Private Jacuzzi
Veronique was so friendly and helpful. She recommended a local car rental agency that picked us up at the airport and brought us directly to Le Colibri and our rental car, saving us the worry of navigating roads and finding our vacation home. The area was quiet at night and Veronique provided amenities such as beach towels and a small cooler that were very useful and saved us the trouble of obtaining/bringing these items ourselves. She checked in a few times and we relied on her recommendations which were all good.
Family- and pet-friendly home rentals

Orient Bay "B&C Collection" 2BD+Sofa
The condo was so close to restaurants, shops and the beach. We loved it there! The beds were comfortable, the ac worked well! It is our plan to return!

Your Paradise Villa
Denis goes out of his way to insure his guests have a wonderful stay at his spectacular villa. His hospitality is top notch, and his property is absolutely perfect for enjoying the beauty and charm of the island. I cannot recommend this host and property any more highly and hope to be able to return in the future.

Villa Kiwi - Collection Villas Saint-Martin
This villa was absolutely stunning and had everything we needed for our stay, as two families with young children. It was minutes from the airport and close to many beautiful beaches and dining options. A car is necessary to get around. We spent lots of time in the pool, enjoying views of the ocean and the sunset in the evening. The villa was also immaculately clean and well maintained. Each room had its own bathroom, as well as an outdoor shower or bath option which we really enjoyed. The only thing to note is the entrance to the third bedroom is from the patio and not the villa itself. It wasn't a big issue for us however, as it was only a few short steps to the villa and we brought cameras to monitor our children in their room at night. All in all, we highly recommend this villa and would come back!

Princess Anouk, Orient Bay, pool, on the beach
Wonderful view of the beach and great patio. House had all the amenities you need for cooking your own meals. This was really nicely placed in the middle of Orient beach so you only have a 10-15 minute walk to all the restaurants for dinner.

Luxurious apartment, direct beach access
Jean Pierre is kind and helpful. helped me to carry the luggages upon check in and check out. The entrance is on a beach and have some stairs which would have been difficult without the help of Jean Pierre! the place is modern and well furnished and have everything you need. the view is spectacular and the beach is right in front so you can hear the sound of the sea while in the apartment. I love that! Its perfect for one person or a couple and I will be back again to my lovely St.Maarten and stay at this place if its available.

Caribbean Dream, Orient Beach. Mont Vernon.
Damiens Apartment is situated in a former hotel, now residence area, so its very quiet. there is direct access to the beach, but while we were there there were a lot of algae, so walking till to the beach chairs and bars took about 15-20min walking on the beach. If you drive its about 10 min drive away to the main square of the beach with all the restaurants and the beach bars. directly at the grounds is a pizzeria which is great for your first day, when you dont havr the energy to go anywhere and still get food. Two other good restaurants are a 2-5 min by car and the supermarket is also just about 5 min away by car and no matter where you are going you always pass the supermarket, so its convenient that its on the way. Contact with Damien was good, he always replied fast. At the beginning we would have wished for a little bit better communication about the water cuts due to a break in the water facility on the french side, but after we asked he sent us to links to newspapers where we could look up the times ourselves. You definitely need a car and there was enough parking space on the grounds. overall we enjoyed our stay at Damiens apartment!

Villa Azur, great view of the Orient Bay
Wait until you see the view! The photos can’t do it justice. The house was clean, comfortable, and so close to the best places to visit on the French side. Highly recommend!

Villa Flagrantia
We loved our stay! The neighborhood is quiet, the location is perfect if you have a car, and the view is beautiful. The secluded beach within walking distance was a real gem, and we enjoyed relaxing in the pleasant shaded dining area in the garden. Everything was exactly as described, and Nada was a wonderful host. Highly recommend!
Family-friendly home 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.

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.

C’est la Vie! Private pool and amazing views !
Very beautiful and pleasant house. Everything was impeccable up to the pool and its terrace to chill at the end of the day Very quiet neighborhood. Ideally located... very close to Grand Case and Orient Bay We would highly recommend this home to all vacationers See you soon Isabelle Fred

Pirat's kingsize bedroom
Our stay was magnificent, the location was central and close to everything, the pool, the views and the accommodation was five stars. Luc and his wife were kind enough to recommend and book us reservations at exceptional restaurants around our Airbnb. I would definitely recommend this place to all my friends.

Condo with a terrace, swimming pool
We staued at Isabelle's for a month snd by the time we left it felt like home. The neighborhood of Oyster Pomd is welcoming with several small but excellent restaurants within an easy walk. There is also a locsl market to pick up fresh bread and other items. Dawn beach is a quick drive. The unit was clean and provided plenty of room for my husband and I as well as space.for our daughter and three friends when they visited. We contacted Isabelle once because the microwave wasnt working and Maxime quickly replaced it with a new one. The one drawback, and only for when we had six people, was that the ad says two bathrooms which is true but there's only one toilet and it oa separate from the bathrooms. It required a bit of planning in the mornings and getting ready to go out out but it was manageable. Overall, we had a wonderful time and would recommend.

Oceanfront Villa with Private Pool
La Casita Villa was worth every penny! Peter is an amazing host, and truly thought of everything! The kitchen is fully equipped with anything you could need including a coffee maker, French press, blender, bottle opener, etc. And even the finer details have been thought of - for example, there is a cooler that they provide to allow you to bring things to the beach and keep cold. Peter was extremely responsive throughout our stay, and very resourceful. We had a maintenance issue with the fridge and Peter immediately had someone there to fix it. The Airbnb itself is stunning. We travelled with 3 couples and we each had our own room, 2 of which had ocean views. It’s the perfect mix of privacy with each room being separated from one another, while still allowed for the most fun and entertainment in the common areas. We spent a lot of time outside under the new gazebo because we could not get enough of the view! The pool overlooking the ocean at sunset is one we will never forget.

Ocean front "colibris" amazing view
It was a perfect place to enjoy the view with the pool. The house was big enough for 6 people. Orient bay is 5 min away for restaurants and beach. We had a wonderful 2 weeks! The host was really reactive to our demands. We will be back!

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 holiday rentals that are family-friendly in Simpson Bay
Total rentals
150 properties
Nightly prices starting at
$255 AUD before taxes and fees
Total number of reviews
2.2K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
120 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace
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