
Holiday rentals with a pool in Simpson Bay
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Top-rated rentals with a pool in Simpson Bay
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Popular amenities for Simpson Bay rentals with a pool
House rentals with a pool

Life's Good
"Life is good" is a secluded villa with a very interesting set up. it has two separate bedrooms with in suite bathrooms on the top level with a separate kitchen and living room as well as a reasonable size infinity pool on a lower level. This would work well for either two couples or parents with preteens/teens of the same sex. The view is to die for. Indigo bay is a heavily developing neighborhood but this villa stands on the opposite side of the bay from the new hotel construction so it is not affected by it at all. There is a short drive to Indigo Bay beach (small and feels private) and another 5 min drive to a nearby grocery store. It is only 10min away from Simpson bay and 15 min from Marigot. it was easy to communicate with the owner of this villa and their local management company who gave us a warm welcome. we definitely plan to come back and spend more time in this lovely place.

Ocean View Villa-Indigo Bay W/Private Pool/0 Steps
This property was absolutely breathtaking. The home looked better in person. Very clean, accessible to most attractions and a beautiful quiet neighborhood. 10/10 experience we will definitely come back!

New-Sunset Place Villa w Stunning Waterfront Views
The villa was perfect. Beautiful view, upscale and clean. Joy was easy to communicate with and offered help with logistics such as car service private yachts, groceries and private chef service. The private pool off our deck was clean and refreshing We started planning our next trip before this one ended.

SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay
Great place !! Loved the location and the villa was beautiful

The best view on the island!
Casa Victoire is one of the best rentals we have ever used for vacation- the pictures do not do it justice and Maly was an amazing host! If you are thinking about staying here just go ahead and click that button and you will not be disappointed. The pool was fabulous overlooking the bay and Pinel Island. Within a few minutes drive of Grand Case and Orient Bay- both with plenty of activities and food. Maly provided so much useful information before arrival and during our stay. The layout worked great for myself and 4 adult children- plenty of space for all. If you rent a car I highly recommend Nono car rental recommended by Maly- car will be waiting on you at the house and they will pick you up at the airport so you can get right to your vacation without worrying about driving as soon as you arrive Thank you Maly- we look forward to our next trip to St Martin!

Luxury Bungalow Sea & Pool View
We loved our stay and can’t wait to return!

Préstige - Luxurious 3 bedroom by the Beach
The host was very pleasant and made herself available to answer any questions. The home was beautiful, clean and had everything we needed to enjoy our trip. The view was amazing and the pics did it no justice. I will be booking again on my next trip to Saint Marteen♥️

Teresa’s Ocean Paradise
Marcus & Jocelyn’s place was extremely nice. The location is about 30 mins from the airport which allowed us to view more of the island. The place was extremely nice, quiet and the view is beautiful. Irene the host was very friendly and provided treats at check in. The home was stocked with plenty of refreshments which was very thoughtful. I truly enjoyed my stay.
Apartment rentals with a pool

Five Star Luxury Beachfront Condo Private Hot Tub
Amazing view and perfect location for a week on the beach and within walking distance of plenty of things to do, places to eat, etc.

FLASH SALE! June-Oct. 2025! Ocean&Tropical Views!
This location is excellent ..everything is near by ..the host is amazing ...thank you for everything its definitely worth it...I wiill be back again and again

cosy apartment
Loved Yoan! So helpful! Met me to help find the apartment and was a gentleman helping with my bags. Space was clean and spotless. Recommended me so many places to see, do and eat. Definitely would come to him again🥰

Maho 1 Bed Condo with ocean view & Free Wi-Fi
Phil is a fantastic host who communicates proactively, ensuring you have all the information you need for a smooth and hassle-free stay. His well equipped apartment is located in Maho Beach, one of the best spots in St. Maarten. From the balcony, you can enjoy views of the sea, the pool, and the island’s famous attraction—the nearby airport—where you can watch planes land right before your eyes. We'll certainly come back!

Brand New- Maho Condo Studio with Seaview and Pool
Our short 3 night stay at Maho Condo was excellent. The space is very clean and small but functional. There are two large closets with plenty of hangers and four drawers of under bed storage. Kitchen: Stocked with glasses, dishes and cutlery as well as appliances like a ninja blender, air fryer and toaster. Bathroom: Rainfall shower with nice pressure, hot water and plenty of towels. They even have darker makeup towels. Misc. Robot vacuum, ironing board, smart tv. Amenities: Fully equipped gym and although we never used the pool it’s a nice size and has plenty of chairs. The onsite security made us feel safe coming and going at night. Location: close to the airport with about a 10 min walk to Maho beach. 5 min drive to Mullet Bay beach. In walking distance to bars/restaurants and the Maho market. We had a car and parked often in the gravel lot across the street. Communication: Great. We got a nice welcome and had an open communication with the hosts should we need anything.

Beachfront 3 bedroom apartment on Simpson Bay
Just returned from our stay and we had an amazing time. The condo is very spacious. Washer and dryer is a must when you visit the beach. We used Mary Boon loungers and umbrella while enjoying drinks and appetizers. There were loungers and umbrellas available but was easier to walk down and sit on the ones already set up :) It was just two of us so was more space than we needed. Would recommend bringing house shoes due to travertine flooring throughout.

'Emerald Pearl' Studio in Maho with Full Amenities
We had the pleasure of staying at the Emerald Pearl Studio in Maho, and it was an absolutely fantastic experience. The studio is well equipped with everything you could possibly need for a comfortable stay-from a functional kitchen to a cozy bed (too soft for us) but that’s our preference. The location is unbeatable, just a short walk to the famous Maho Beach,where you can enjoy beautiful sunsets,watch planes fly overhead, or just relax by the ocean. It’s also conveniently located near some great restaurants, bars, shops and a supermarket. The host was incredibly accommodating and provided excellent communication she even left me a bottle of wine for my birthday which I thought was very nice and she even let us check in early. I recommend renting a car for the whole island experience, but taxis are only a 5 minute walk away. If you’re looking a relaxing, comfortable and stylish place to stay in Maho I recommend Emerald Pearl Studio. I will definitely be returning. 2 ppl only ;)

Island Time- Luxurious 2 BR Condo. Stunning views!
This place is absolutely beautiful! Photos don’t do it justice, it’s even better in person. My man and I had this place to ourselves but it’s perfect for 2 couples. Balconies in both rooms and full bathrooms! It’s also in a perfect area very close to Maho plaza but you absolutely need to rent a car. I didn’t want to leave, it’s so beautiful and peaceful! I will definitely come back here for my next trip to Sint Maarten & Anguilla.
Quick stats about holiday rentals with a pool in Simpson Bay
Total rentals
230 properties
Nightly prices starting at
₹5,138 before taxes and fees
Total number of reviews
5.6K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with dedicated workspaces
100 properties have a dedicated workspace
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