
Vacation rentals with a pool in Simpson Bay
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Simpson Bay
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Simpson Bay rentals with a pool
House rentals with a pool

Villa Taïana - Oyster Pond
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 🙏🏾

Spacious villa 8 people swimming pool sea view
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!

New-Sunset Place Villa w Stunning Waterfront Views
My best friend and I enjoyed the house. It was the perfect home base for our island adventures peaceful, private, and just as described. The views were beautiful, and we loved having our morning coffee outside while listening to the water. The location made it easy to get around the island, and everything felt safe and convenient. The house was clean, cozy, and had everything we needed, from a well-equipped kitchen to comfortable beds. The host was friendly, responsive, and made sure we had everything we needed before and during our stay. We had such a great time and would absolutely stay here again the next time we visit St. Maarten. Can’t wait to return!

Villa Louisiana
Villa Lousiana was a wonderful place to stay in Orient Beach. The restaurants and stores are a short walk around the corner. The property is private and the pool was great to cool off. Virginie was a gracious host!

Villa Carib sxm piscine.
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

Water access, snorkeling gear & kayaks
Our stay at this Airbnb in St. Martin was incredible! The place was exactly as described and looked just like the photos—beautiful, clean, and well-stocked with everything we needed. The hosts were fantastic—super responsive and even helped us coordinate in-house massages, which was such a treat. One of the highlights was the kayaks, which we highly recommend using to visit Pinel Island—an unforgettable experience! This rental truly exceeded our expectations, and we wouldn’t hesitate to stay here again if we return to the island. Highly recommend!

Maison les Sucriers, Baie Orientale, Le Village
Fantastic location for a relaxing stay, within minutes of the beach and excellent restaurants, markets, and local gym.

Prestige Too - Luxurious 2 bedroom
Sharina place was beautiful. My family and I enjoyed our stay very much. Sharina was warm, friendly, and responsive when necessary. The home was incredibly spacious, serene, and peaceful. My son enjoyed the pool while my husband and I took in the views. The home is secure and in a safe place as well. Many beaches within a few mins drive. There’s a nice grocery store about 8 mins drive to the home. Thank you for an incredible stay Sharina. And thank you for your understanding with my mishap with checkout. My apologies. Be safe and well.
Condo rentals with a pool

Loft Condo - STEPS FROM BEACH!
Jayne provided exceptional hospitality, exceeding our expectations. The accommodations were pleasing and well-maintained, offering a comfortable and convenient stay. The location was within walking distance of the beach and had many restaurants nearby. Jayne’s prompt and efficient response to our inquiries was truly remarkable. She effectively addressed any challenges we encountered, demonstrating a genuine commitment to guest satisfaction. On our initial night, an air conditioning malfunction occurred. Despite the inconvenience, Jayne promptly offered alternative solutions and promptly refunded our first night’s stay. She arranged for the necessary repairs to be completed the following day. Jayne’s exceptional hospitality extended beyond her professional responsibilities. She even left us a bottle of wine! Her genuine care and concern for her guests make her an outstanding host. I highly recommend staying with Jayne, as she offers an exceptional guest experience.

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
This was a very safe and secure unit in the heart of Simpson Bay. The unit was perfect for our stay, nicely furnished, had fantastic outdoor space and was quite comfortable. The hosts Mariana and Manoj are great communicators who made us feel very cared for while at the property! Thank you both so much for a great stay!!

The Cliff in Cupecoy Beach HEAVEN!!!
Wow, where do I even begin? Our stay at The Cliff was truly unforgettable. Everything about this condo exceeded our expectations. The listing was 100% accurate, but honestly, the pictures don’t do it justice. The space is even more beautiful in person! Spacious, spotless, and so comfortable. The ocean views from the condo were absolutely breathtaking, and having the beach right at our footsteps was a dream come true. The pool was pristine and relaxing, and we loved that Mullet Bay was just a short walk away. We also felt incredibly safe the entire time, which made the experience even more enjoyable. Special shout-out to Joe, the host—he was AMAZING! So friendly, helpful, and always just a message away. You can tell he genuinely cares about your experience. I would 100% stay here again and again.

Utopia Condo: Cozy, Quiet & Central with a Pool
A real favorite! This accommodation perfectly combines comfort, elegance and functionality. Every detail has been carefully thought out, from the choice of materials to the warm decor that creates a welcoming and soothing atmosphere. The space is bright, impeccably clean and perfectly equipped, offering everything you need for a pleasant stay. Special mention for the host, who was remarkably kind and available. A property that I would recommend without hesitation and where I will be happy to come back.

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!

MAYA, Elegant Condo T2, Swimming Pool - Pinel
My husband, two year old daughter and I had the best time at Severine’s place. The home is beautiful and Séverine is an extremely responsive and communicative host. The outdoor terrace was used a ton. The pool is okay- we only used it once, we were mostly at the ocean. Who goes all that way to use the pool anyway?! Great quiet little neighborhood and close to orient bay. Amazing boulangerie up the street! The only thing I’ll mention is that to get into the apartment for the first time I had to message Séverine so she could let me in remotely, so I had to keep my phone on. I was hoping to avoid having my phone on data for the entire vacation. Not a big deal but something to note! Overall would highly recommend!

The Beach Condo
Roel was great. The condo was exactly as described and Roel was very responsive/helpful. Would fully recommend to anyone!

Luxury Little Bay- Caribbean Blue
We enjoyed every minute of our stay! The condo had everything we needed. Very comfortable beds and a great kitchen! The lanai and pool were a wonderful addition! We also felt very safe at this location.
Home rentals with a private pool
Quick stats about vacation rentals with a pool in Simpson Bay
Total rentals
230 properties
Nightly prices starting at
$60 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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