
Vacation rentals with a pool in Cupecoy Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cupecoy Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Cupecoy Beach rentals with a pool
House rentals with a pool

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!

Pelican Paradise
Perfect little villa (actually much bigger than we expected), located in the best neighbourhood of St-Maarten, and managed by a true Superhost!

Villa Louisiana
This place was amazing. It was exactly as it was described. We had anywhere from 2-8 of us at a time and there was plenty of space and bathrooms also worked out great. We would go back here again.

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!

Modern 3BR with Private Pool
I stayed there with my family for my birthday and it was great. The location was great had stores near by . The host was great helped with the check-in and instructions. The place was gorgeous and clean. The pool was great. They cleaned it every morning. The personal touches like their welcome board with your name was a great surprise. Thank you for that. Definitely booking them again when I’m going back with my mom. Thank you for the great stay.

Sunset Views Designer 3 Bedroom House
Dans place was beatiful and perfect for our family of 4. 2 girls, 6 years and 3 years old. The Island is very small and you can drive everywhere in 30 minutes. The house is clean with a great porch for sunsets and pool for the kids. There was fun wildlife (lizards and humming birds) for the kids to see on the property. The property is walking distance for our 3 year old to kimsha beach, restaurants, and a grocery store. We took ferries to st.barts and anguilla during our week at Dan's place which were driveable in 15 min to their respective terminals. Bathrooms were clean, beds were soft and house is fully stocked with all our needs. We could not have imagined a better time or had a better host.
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.

Beautiful, airy 2BR condo overlooking Dawn Beach
All around a great place to stay, one needs a car to get around to beaches and food stores. The views from our balcony was beautiful would 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
Destinations to explore
- Luxury rentals Cupecoy Beach
- House rentals Cupecoy Beach
- Apartment rentals Cupecoy Beach
- Rentals with a hot tub Cupecoy Beach
- Waterfront rentals Cupecoy Beach
- Rentals with outdoor seating Cupecoy Beach
- Rentals with a patio Cupecoy Beach
- Villa rentals Cupecoy Beach
- Rentals with a sauna Cupecoy Beach
- Beachfront rentals Cupecoy Beach
- Fitness-friendly rentals Cupecoy Beach
- Pet-friendly rentals Cupecoy Beach
- Smoking-friendly rentals Cupecoy Beach
- Rentals with beach access Cupecoy Beach
- Family-friendly rentals Cupecoy Beach
- Condo rentals Cupecoy Beach
- Rentals with a washer and dryer Cupecoy Beach
- Rentals with pools Sint Maarten
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom