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House vacation rentals in Simpson Bay

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Popular amenities for Simpson Bay house rentals

House rentals with a pool

Guest favorite
The villa features a spacious terrace with a private swimming pool, showcasing clear blue water. The open layout includes multiple seating areas and large glass doors that provide access to the indoor living space, all set against a clear blue sky.

Home in Collectivité de Saint-Martin

5 out of 5 average rating, 5 reviews

Villa Taïana - Oyster Pond

DarineRating, 5 stars5 months ago
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 🙏🏾
Superhost

Home in Cul-de-Sac

4.86 out of 5 average rating, 14 reviews

Maison Ti Case, Private Pool, Near Pinel Island

AudreyRating, 5 stars6 months ago
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.
Guest favorite

Home in St Maarten

4.96 out of 5 average rating, 57 reviews

Villa Vijoux Luxury, Modern OceanView 8 Bedrooms

VeronicaRating, 5 stars1 week ago
“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!
Guest favorite
A private swimming pool is framed by white walls, offering clear views of the turquoise Caribbean Sea. Lush palm trees can be seen in the background under a bright sky, creating an inviting outdoor space.

Home in Caribbean

4.88 out of 5 average rating, 52 reviews

Pelican Paradise

JohnRating, 5 stars7 months ago
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)!
Superhost
A private pool is surrounded by lush greenery and colorful flowers, providing a serene outdoor retreat. Reclining lounge chairs are positioned along the poolside, inviting relaxation in the sunlit space. The clear blue sky complements the tranquil atmosphere of the garden.

Home in Collectivité de Saint-Martin

4.84 out of 5 average rating, 19 reviews

Villa Louisiana

AdamRating, 5 stars2 weeks ago
Highly recommend staying here.
Superhost
A modern home exterior is shown with a light-colored facade and expansive windows. A private pool is situated in front, surrounded by a clean patio space. Two lounge chairs are positioned nearby, inviting relaxation under a bright blue sky.

Home in Mont vernon 3

4.67 out of 5 average rating, 3 reviews

Villa Carib sxm piscine.

AshantiRating, 5 stars8 months ago
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
Superhost
A private pool is framed by wooden decking, with lounge chairs positioned nearby for relaxation. The surrounding fencing creates a sense of seclusion, while the vibrant buildings of the residence are visible in the background, complemented by palm trees swaying gently in the breeze.

Home in Parc de la Baie Orientale

4.8 out of 5 average rating, 10 reviews

Maison les Sucriers, Baie Orientale le Village

ChristineRating, 5 stars2 months ago
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!
Guest favorite
A turquoise pool with a curved edge is bordered by a sleek white deck and palm trees. A shaded seating area with white lounge chairs offers a place to relax. The backdrop features clear water and distant hills under a partly cloudy sky.

Home in Philipsburg

5 out of 5 average rating, 13 reviews

3 Bedroom Ocean Front Villa, Private Infinity Pool

AndrewRating, 5 stars2 weeks ago
Ideal location for a family vacation with friends. Michelle was very responsive and made us feel at home!

Weekly house rentals

Guest favorite
A sunny outdoor area features a round heated pool surrounded by wooden decking. Several lounge chairs with turquoise cushions are positioned around the pool. A covered seating area is visible in the background, enhancing the space for relaxation.

Home in Orient Bay

5 out of 5 average rating, 13 reviews

Villa Galapagos, 3 Bedrooms, Orient Bay Beach

SteveRating, 5 stars7 months ago
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
Guest favorite
An outdoor terrace presents a private pool with clear blue water, surrounded by wooden decking and tropical plants. Palm trees sway in the background, while a scenic view of the sea and distant boats is visible under a bright, blue sky.

Home in RUE DES GRANDES CAYES

4.88 out of 5 average rating, 17 reviews

VILLA "LES VENTS DE PINEL" EXCEPTIONAL SEA VIEW!

DanielRating, 5 stars1 month ago
We had a wonderful stay at Julie's place. The pool and view were were so peaceful. It was just the escape we needed!
Superhost
A vibrant mural showcases a colorful underwater scene depicting marine life including a turtle, dolphins, and various coral formations. The mural features the text 'St. Maarten' prominently, surrounded by shades of blue and bright colors, highlighting the local coastal theme.

Home in Simpson Bay

4.87 out of 5 average rating, 15 reviews

Sea La’Vie — 2mins walk from the beach!

SusanRating, 5 stars1 week ago
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 .
Superhost
A charming terrace is displayed with comfortable wicker seating arrangement and a small table. A scenic view of the ocean is visible in the background, framed by tropical plants. The space is designed for relaxation with wooden flooring and a covered area providing shade.

Home in Collectivité de Saint-Martin

4.78 out of 5 average rating, 18 reviews

Blue Horizon villa

YvonneRating, 5 stars1 month ago
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!
Guest favorite

Home in Collectivité de Saint-Martin

5 out of 5 average rating, 13 reviews

Prestigious Villa with Breathtaking Ocean View

LoriRating, 5 stars3 days ago
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.
Guest favorite
A shaded terrace features comfortable seating with blue cushions, overlooking a private pool and sea views. A small coffee table sits in the center. Lush greenery and palm trees are visible in the background, enhancing the serene outdoor space.

Home in Cul-de-Sac

4.94 out of 5 average rating, 35 reviews

Villa Zen : confort et luxe vue mer St Martin

DanielRating, 5 stars1 month ago
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.
Guest favorite
A charming oceanfront villa is surrounded by well-manicured gardens, showcasing lush greenery and vibrant flowers. The two-story structure is complemented by a tiled roof and large windows, offering picturesque views of the horizon during twilight.

Home in Upper Prince's Quarter

5 out of 5 average rating, 20 reviews

St. Maarten Villa Caribbean Jewel "THE JEWEL"

rebeccaRating, 5 stars1 month ago
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
Guest favorite
The exterior of a two-story villa is displayed, featuring a blue roof and white walls. Green grass surrounds the property, with potted pink flowers positioned near the walkway. Lush greenery and distant hills provide a natural backdrop against a blue sky with scattered clouds.

Home in Collectivity of Saint Martin

4.91 out of 5 average rating, 92 reviews

Coconut Beach Villa Sxm

MelleRating, 5 stars2 months ago
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 reviews

Pelican key - BEACH FRONT Villa

TimRating, 5 stars2 weeks ago
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!
A private swimming pool is surrounded by palm trees and vibrant greenery. Two red loungers are positioned beside the pool, complemented by beach towels. The serene environment invites relaxation under clear blue skies.

Home in Orient Beach

4.75 out of 5 average rating, 12 reviews

Nice Villa for 6 Orient Bay Beach

RosioRating, 5 stars25 months ago
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.
Superhost
A spacious sleeping area features a large yellow bedspread complemented by two decorative pillows. Nightstands with lamps flank the bed, and a wall mirror provides depth to the room. Natural light illuminates the space through a nearby window.

Home in Simpson Bay

4.66 out of 5 average rating, 38 reviews

Prospère villa

ShellyRating, 5 stars1 month ago
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.
Superhost
A vibrant view of the coastline and distant hills is framed by the greenery of palm leaves and a tall cactus. The blue rooftops of nearby houses contrast with the clear blue water, creating a serene outdoor setting.

Home in Collectivité de Saint-Martin

4.87 out of 5 average rating, 15 reviews

NEW House 2 bathrooms, 3 terraces and ocean view

AriannaRating, 5 stars3 weeks ago
Great location! Very nice and clean
The exterior of a single-family home is illuminated under a twilight sky, showcasing a welcoming entrance. Soft lighting highlights the outdoor areas, including a shaded patio. Surrounding greenery adds a touch of nature, contributing to a tranquil evening atmosphere.

Home in Simpson Bay

4.8 out of 5 average rating, 10 reviews

Casa Coral, Sint Maarten

NancyRating, 5 stars11 months ago
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 reviews

Caribbean Style Family Home

TanzaniaRating, 5 stars1 month ago
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.
A private swimming pool is surrounded by lush palm trees and green landscaping, offering an ocean view. Clear blue skies with scattered clouds create a bright atmosphere, enhancing the tranquility of the outdoor space.

Home in Collectivity of Saint Martin

4.78 out of 5 average rating, 37 reviews

Very pleasant ocean view house with swimming pool

JulieRating, 5 stars23 months ago
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!!
A serene swimming pool is surrounded by a wooden deck, featuring lounge chairs for relaxation. Lush greenery and rocky outcrops frame the area, while a clear blue sky with clouds creates a tranquil backdrop. Sun floats and an inflatable ring add a playful touch to the scene.

Home in Cul-de-Sac

4.89 out of 5 average rating, 36 reviews

C&S Home; Spacious 3 BDR 2.5 BTHR with sea view

JamieRating, 5 stars2 weeks ago
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

Destinations to explore