
Vacation rentals with a pool in Cupecoy Beach
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Top-rated rentals with a pool in Cupecoy Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Cupecoy Beach rentals with a pool
House rentals with a pool

My Paradis Bleu beach house!
Villa Flamingo was absolutely perfect! Even better than the photos. It was roomy, clean, extremely well appointed and Christine was a dream to communicate with. Alexandre was also very helpful and stopped in upon our arrival to make sure everything was okay. Everything we needed for our stay was there, including items we didn't expect, such as beach accessories and snorkels! The kitchen had all the equipment needed and some helpful basics such as salt/pepper/oil/coffee. The location is perfect since we had a view of the ocean, which was a two minute walk, and the Orient Bay courtyard with its restaurants and shops meant we never needed to use our car! It was nice to have real people nearby as we had quick answers to real-time questions. We will definitely be back and can't imagine staying anywhere but in their properties.

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
Had the most amazing stay thanks to Joy. She was very responsive and helpful - providing great suggestions for restaurants and things to do nearby. The villa was beautiful - just as pictured!

Villa Louisiana
Virginie was a great host - responded in a timely fashion to all my questions and provided clear useful answers. Property was great. Location can't be beat. Would strongly recommend.

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
We had a very nice stay. The location of the house is fantastic and is close to all restaurants, beach grocery store. The host was very flexible when we arrived and we are very grateful for that . The place was very clean and well maintained. We'll definitely be back! Thank you!
Condo rentals with a pool

Loft Condo - STEPS FROM BEACH!
We 100% recommend staying at Jayne's place. She was so helpfully with car rental, changing dates due to flight trouble, and making sure to answer all our questions about SXM. The location worked great for us, our son loved the pool and how close location is to Mullet beach. We had a rental car, but if you do not you have a good selection of food places, grocery stores, beach, casino all within easy walking distance. Location felt very safe, with gated area and night guard on site. Pool and seating area was a great space to spend time and relax. We well for sure be booking with Jayne again when we return to SXM.

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!!!
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

Utopia Condo: Cozy, Quiet & Central with a Pool
We had a great stay in Anne Karine's apartment! Ideally located just on the edge of Marigot, perfectly quiet and a nice view over the lagune. The apartment is spacious, nicely decorated, has AC in both the living room and the bedroom and it has everything you need. The kitchen is perfect to make dinner, there are extra pooltowels, you can borrow a beach parasol and little chairs and dining outside is very cosy. We absolutely loved our stay and the communication with Anne Karine was excellent. Very higly recommended!

Maho 1 Bed Condo with ocean view & Free Wi-Fi
From the very beginning Phil was very helpful and personable. Phil was very detailed on the instructions for check-in and the surrounding area. He provided recommendations for things to do and places to eat. He inquired if we had any questions or concerns, making us feel comfortable and at ease with renting from him. He already had pretty much covered 99.9% of the information that would have been needed, therefore we felt pretty much at home being in his place. We loved how well stocked the unit was re: towels, linen, kitchen supplies, the peacefulness of the unit and the cleanliness (which is definitely a plus plus for us) but above all the view from the unit was to die for. We enjoyed our time very much especially when lounging at the pool. We were especially grateful that he accommodated our check-out time. We will definitely be back. Thank you Phil for being a great host.

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
We have been coming to SXM for 15 years and I have stayed all over the island and this is my favorite. The beach, the pool, at your doorstep, it is beautiful! You can't ask for anymore. I have already rebooked for next year!

Little Bay- Caribbean Blue View, 2 bed, sleeps 6
Lovely location! Really enjoyed our stay here and would definitely come back. Felt very homey and comfortable, it was perfect. The view was amazing and made the hill up 100% worth it. You really get used to the drive after the first time. There's an amazing beach called Great Bay Beach right near by and a great on the beach restaurant called Eat Something. Ask for Lenny if you want to eat and rent chairs there, he's the best!
Home rentals with a private pool
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