
Vacation rentals with a pool in Simpson Bay
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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

Home in Collectivité de Saint-Martin
5 out of 5 average rating, 5 reviewsVilla 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 🙏🏾

Home in Koolbaai
5 out of 5 average rating, 11 reviewsNew-Sunset Place Villa w Stunning Waterfront Views
If this space is available for your selected dates, BOOK IT! Joy was an amazing host who was insightful, flexible and attentive. Her space offered everything 3 couples could ask for: comfy furniture, ample amounts of fan and a/c units, outdoor lounge seating and a great sized pool with gorgeous infinity views of the ocean. Location served its purpose as it is away from most noise of airport and local traffic. Although not exactly walkable from nightlife in the area, a short and affordable cab ride was easy to call. Thank you joy!

Home in Caribbean
4.88 out of 5 average rating, 52 reviewsPelican Paradise
This place is so great that we had to make a return trip. Just like the first time, John's place was excellent. The weather is definitely warm during the summer, so we were thankful for the A/C to keep things cool at night. The pool was great, and the house was stocked with more than enough beach/pool towels to last us all week with 4 people. It was also nice to be able to wash any wet/dirty laundry before packing it up for the return trip. Another wonderful vacation thanks to John's house, we'll definitely be back again (again)!

Home in Collectivité de Saint-Martin
4.84 out of 5 average rating, 19 reviewsVilla Louisiana
Highly recommend staying here.

Home in Mont vernon 3
4.67 out of 5 average rating, 3 reviewsVilla 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

Home in Cul-de-Sac
5 out of 5 average rating, 40 reviewsWater access, snorkeling gear & kayaks
Our experience at Villa Ocean was truly fantastic. Melissa, Nina and Kevin were extremely proactive prior to our arrival, providing suggestions for activities and restaurants, as well as helping us navigate new travel requirements. They were also incredibly responsive to any and all questions we had during our stay, and generously made lunch reservations for us so we could make the most of our final hours on the island. Kevin was fantastic helping us find the villa in the dark upon our arrival, and provided a thorough overview of the villa and all its amenities. The villa itself is perfect. It looks exactly like the pictures, and proved to be a great size and set-up for our two families. We lived on the outdoor deck with the doors open to the interior - it was truly heaven. The view of the water and Pinel Island were a spectacular way to begin and end each day. We also made frequent use of the kayaks, making trips out to the sandbar and to Pinel Island. You will not regret booking it!

Home in Parc de la Baie Orientale
4.8 out of 5 average rating, 10 reviewsMaison 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!

Home in Cole Bay
4.98 out of 5 average rating, 43 reviewsModern 3BR with Private Pool
Cannot say enough positive things about Sabrina. She was a fantastic host and the place is exactly as pictured- spacious, clean, and great decor. Any questions we had were responded to very quickly. She also helped us out even after check-out when our flight was cancelled. Great location and central for exploring the island and its beautiful beaches. Thank you for everything Sabrina!!!
Condo rentals with a pool

Condo in Lowlands
4.78 out of 5 average rating, 74 reviewsLoft Condo - STEPS FROM BEACH!
Accommodated me last minute, very helpful the entire time. No issues with the room, beautiful location.

Condo in Simpson Bay
5 out of 5 average rating, 32 reviewsCasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
Back from vacation and already missed the place. Feels very homey. The view from the bottom balcony was exceptional. Manoj and Mariana were very responsive with excellent communications no matter what time of day. The house on the water inside a gated area was great. Private parking. A fully equipped house. We loved the fact that we had a washer and dryer. Beds were comfortable. Fully equipped kitchen and a bbq is a plus if you decide to bbq. We loved the guestbook idea, where you get to read other guest experiences and favourite places to visit and eat. The location is excellent especially you rent a car. Otherwise, you’re surrounded by grocery stores, restaurants, cafes and bus stops. Thank you Manoj for everything, we loved SXM and we hope to return soon.

Condo in Lowlands
5 out of 5 average rating, 37 reviewsThe Cliff in Cupecoy Beach HEAVEN!!!
Staying at Joe’s place was by far the best decision for an airbnb in St. Maarten. Between a beautiful private beach off The Cliff, an awesome infinity pool, and wide patio with a view of- I couldve stayed there the whole time and been content with the trip. The near by restaurants, grocery stores and things to do less than a mile or so drive made everything so convenient. Will certainly be coming back!

Condo in Marigot
4.98 out of 5 average rating, 50 reviewsUtopia Condo: Cozy, Quiet & Central with a Pool
We stayed in Anne's apartment for a few days between our holiday in Orient Bay and flying out home, we wanted somewhere conveniently close to Marigot, shops and restaurants and Anne's place was just what we wanted. The place was clean, equipped with all modern amenities and the sunsets were beautiful. Anne was super proactive in her communication.

Condo in Lowlands
4.88 out of 5 average rating, 40 reviewsMaho 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.

Condo in Upper Prince's Quarter
4.83 out of 5 average rating, 6 reviewsBeautiful, 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.

Condo in Simpson Bay
4.98 out of 5 average rating, 61 reviewsThe 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!

Condo in Little Bay
4.94 out of 5 average rating, 18 reviewsLittle Bay- Caribbean Blue View, 2 bed, sleeps 6
Tracy place was absolutely amazing—so comfortable, beautifully maintained, and in such a great location, especially the amazing views. St. Maarten is truly a paradise, and staying at her place made the experience even more special. We loved every moment, from relaxing having a coffee looking at the amazing views to relax in the pool with the family, and exploring the stunning surroundings. It was an absolute pleasure, and we’re so grateful for the opportunity to share in the beauty of Tracy wonderful space. We hope to return one day and create even more amazing memories! Note: First impressions of the road to the villa was surprisingly steep but after a few drives , you get used to it. I would say, it prep you for all the adventures on the island.
Home rentals with a private pool
Quick stats about vacation rentals with a pool in Simpson Bay
Total rentals
220 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
5.1K 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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