
House vacation rentals in Simpson Bay
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Top-rated house rentals in Simpson Bay
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Popular amenities for Simpson Bay house rentals
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 Cul-de-Sac
4.86 out of 5 average rating, 14 reviewsMaison Ti Case, Private Pool, Near Pinel Island
Had a great week in this home. The location was great for me as I was looking for rest. We were able to take advantage of the swimming pool as a family. The property is removed while being close to a shopping area and Grand Case Airport.

Home in St Maarten
4.96 out of 5 average rating, 57 reviewsVilla Vijoux Luxury, Modern OceanView 8 Bedrooms
“Nisha’s place was absolutely amazing! From start to finish, Manoj was incredibly responsive and acted as a fantastic concierge, providing great recommendations—including cake vendors that made my 50th birthday even more special. The villa was beautiful and made for a perfect celebration. The only small downside was the lack of TVs in the bedrooms, but everything else more than made up for it. Highly Recommend!

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 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 Philipsburg
5 out of 5 average rating, 13 reviews3 Bedroom Ocean Front Villa, Private Infinity Pool
Ideal location for a family vacation with friends. Michelle was very responsive and made us feel at home!
Weekly house rentals

Home in Orient Bay
5 out of 5 average rating, 13 reviewsVilla Galapagos, 3 Bedrooms, Orient Bay Beach
This was our 2nd stay at Villa Galapagos and was even better than our stay last year. The new outdoor table and chairs are a huge improvement and is an ideal dining space. The new SXM beach towels were a nice addition. You can check my prior review which includes info on the bedrooms, bathrooms, kitchen and outdoor cooking facilities. Those were all outstanding as they were last year. Philippe is responsive when a question comes up. Check in is super simple. We highly this Villa

Home in RUE DES GRANDES CAYES
4.88 out of 5 average rating, 17 reviewsVILLA "LES VENTS DE PINEL" EXCEPTIONAL SEA VIEW!
We had a wonderful stay at Julie's place. The pool and view were were so peaceful. It was just the escape we needed!

Home in Simpson Bay
4.87 out of 5 average rating, 15 reviewsSea La’Vie — 2mins walk from the beach!
We liked the location for the easy walk to nice beaches & restaurants. Sunset Beach is a must if you’re an airplane enthusiast. Those jumbo jets buzz right over head to land!And the restaurant & bar are a nice plus. There is a beach just a few minutes walk from the house in front of D’s restaurant- they don’t mind at all if you use their chaise chairs & they will serve you in the beach. The kitchen & bathrooms are well stocked. Only bummer was there really wasn’t a decent outdoor space .

Home in Collectivité de Saint-Martin
4.78 out of 5 average rating, 18 reviewsBlue Horizon villa
Wonderful Stay in Saint Martin! We had an amazing time at this villa! The space was spotless, comfortable, and well-appointed, with a beautiful pool offering breathtaking views. And lots of outdoor seating . The location was perfect—peaceful yet close to beaches and restaurants. Olivier was very responsive and helpful, making our stay seamless. Highly recommend and would love to return!

Home in Collectivité de Saint-Martin
5 out of 5 average rating, 13 reviewsPrestigious Villa with Breathtaking Ocean View
We very much enjoyed our stay at Marion’s beautiful home. It was well laid out, easy to get around, had plenty of parking, an awesome pool, and great kitchen. The bedding was comfortable and had all the amenities one could need. We were able to completely relax and enjoy our time. The breeze off the ocean and the surrounding hills gave us all the coolness we needed as well. The island is easy to get around as well. We enjoyed Grand-case and all the other places we visited. Wonderful stay! Highly recommend.

Home in Cul-de-Sac
4.94 out of 5 average rating, 35 reviewsVilla Zen : confort et luxe vue mer St Martin
Beautiful property with a wonderful view. Very private but only a quick drive from the beach, restaurants, grocery store, etc. You’ll have everything you need for a comfortable stay at this villa. Would highly recommend to anyone considering a stay here.

Home in Upper Prince's Quarter
5 out of 5 average rating, 20 reviewsSt. Maarten Villa Caribbean Jewel "THE JEWEL"
What a magical week! Thank you for sharing your exquisite home with us! Our family of 11 was more than comfortable at the Jewel. There was plenty of room to spread out, so we never felt like we were on top of eachother. There are 6 showers, so getting ready to go from the day at the beach to dinner time was always a quick turnaround! The outdoor shower was just dreamy.... The villas serene setting, perched on the side of the hill, with unobstructed views of St Barths & the ocean was breathtaking. Many memories (& insta posts!) were made & will definitely refer to friends and family... Ursula is pure sunshine & spoiled us rotten! From accompanying us to the market, & preparing our meal on arrival, as well as apple pie, gluten free muffins, passionfruit cocktails & her traditional Christmas cake! Ginny was always available with quick responses to our inquiries prior to arrival & had terrific recommendations! 5 stars all around & we hope to return!! xo

Home in Collectivity of Saint Martin
4.91 out of 5 average rating, 92 reviewsCoconut Beach Villa Sxm
Great location, close to several beaches in walking distance. Close to Grand Case with it's restaurants in walking distance. Nice villa, good swimming pool, spacey garden. View on the green mountains. Easy to check-in and check-out. Clear instructions.
Private house rentals

Home in Koolbaai
5 out of 5 average rating, 3 reviewsPelican key - BEACH FRONT Villa
What an amazing property, right on the water in a quiet Sint Maarten neighbourhood. The views were spectacular. Alexandra was the perfect host and very kind, always available to answer questions and provide suggestions for things to do. The interior of the unit was perfect for our family with 3 separate bedrooms and lots of sleeping space. The kitchen was fully equipped, and we made good use of it. I would definitely recommend Alexandra’s beach front villa! Thanks Alex!

Home in Orient Beach
4.75 out of 5 average rating, 12 reviewsNice Villa for 6 Orient Bay Beach
You couldn’t ask for a better location. It’s steps away from some of the best beach bars in Orient Bay. The house has a lovely deck on the 2nd floor with great views of the water and hills. Very peaceful. And there were some very thoughtful welcome amenities provided at checkin. Overall a great stay.

Home in Simpson Bay
4.66 out of 5 average rating, 38 reviewsProspère villa
Great location, close to Maho beach. Walkable to many attractions Jusnel is very responsive and always available for questions. Would definitely stay there again on our next trip.

Home in Collectivité de Saint-Martin
4.87 out of 5 average rating, 15 reviewsNEW House 2 bathrooms, 3 terraces and ocean view
Great location! Very nice and clean

Home in Simpson Bay
4.8 out of 5 average rating, 10 reviewsCasa Coral, Sint Maarten
Shelby was very attentive to our needs. Water is not hot but that apparently is what the island has. Water pressure is not the greatest but did the job. Being beside the airport was very convenient but not quiet. We all had a great trip and appreciate Shelby a lot.

Home in Upper Prince's Quarter
4.95 out of 5 average rating, 41 reviewsCaribbean Style Family Home
Great place to stay. I stayed with 3 friends and it was amazing. Judy was great she communicated well, even waited for us until nighttime to guide us to the airbnb to ensure we made it in okay and didn’t get lost. Only cone is that there were ants and the drive way to get into the Airbnb is very bumpy and can damage your car we had to pay $250 for a bumper because it was too low for the driveway. Other than that it was a great stay and I would recommend.

Home in Collectivity of Saint Martin
4.78 out of 5 average rating, 37 reviewsVery pleasant ocean view house with swimming pool
Thierry’s house was perfect, clean, beautifully decorated, lovely outside space, we loved the little pool ….. it was just perfect, the photos don’t do it justice. Colette who met us was lovely too and very helpful We would return in a heartbeat!!

Home in Cul-de-Sac
4.89 out of 5 average rating, 36 reviewsC&S Home; Spacious 3 BDR 2.5 BTHR with sea view
Staying at the Alizea residence was wonderful. I have to compliment that it was the best stocked kitchen I’ve ever had staying at an air bnb before. The home was cleaned very nicely and she left clear directions on everything for us. The gated location and keypad door made us feel that much more secure. Locally there is lots to do in that area, Pinel island is just minutes up the road and Anse Marcel is right over the hill. Highly recommend Pepe’s pizza right around the corner 4 minutes and it was lovely to have the Super U also 4 minutes away. The one complaint that I can think of which wouldn’t deter me from returning was I wish the pool was in better condition. I understand that it is a shared pool so no fault of Chrissy. Thank you for having a beautiful home for us to stay in during our trip to SXM.
Quick stats about house rentals in Simpson Bay
Total rentals
20 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
490 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Wifi availability
20 properties include access to wifi
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