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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
A spacious outdoor terrace features a private pool that reflects the sky and surrounding landscape. Lounge chairs are positioned poolside, offering space for relaxation. A distant green hill is visible, complementing the serene atmosphere. The villa is partially visible through large sliding doors.
Home in Little Bay
4.95 out of 5 average rating, 81 reviews

Villa Kailani 4 bedroom with Stunning Ocean Views

BillRating, 5 stars3 months ago
Awesome home with a relaxing feel, unbelievable views and very comfortable setting for 8 people. This is our second stay and can’t wait to come back again. Every bedroom has a picturesque view and sunrises are beautiful. There is ample room for everyone with multiple outdoor seating areas and a huge pool deck. Maayke is a great host who was super helpful and very quick to respond to questions. Absolutely recommend this place for an unforgettable vacation.
Superhost
A private pool is framed by a wooden deck, with lounge chairs positioned for relaxation under the sun. A covered terrace area offers a dining table, enhancing outdoor living. Lush greenery surrounds the property, with a palm tree adding a tropical touch.
Home in Cul-de-Sac
4.88 out of 5 average rating, 16 reviews

Maison Ti Case, private pool, near Pinel Island

SuzanneRating, 5 stars3 weeks ago
We had a very nice stay. Everything was clean and tidy. Glad the kitchen is so complete! Wonderful swimming pool. Slept well on the good beds. Private, in a nice and quiet area on Sint Maarten. Neighborhood is closed evening and night with a closed gate, safe 👍 Mr. Gilles always responds quickly and kindly. I said I missed tea towels, they were quickly bought and delivered to us. I definitely recommend this place!!
Guest favorite
A tranquil pool reflects the azure sky and distant boats. Surrounded by lush greenery, the pool area features a cascading waterfall and is bordered by smooth stones. A wooden partition provides privacy, enhancing the serene atmosphere of the waterfront retreat.
Home in Collectivity of Saint Martin
4.88 out of 5 average rating, 77 reviews

ALMOND BLUE ...Pinel bay view - caribbean feeling

JoelRating, 5 stars2 months ago
Villa Almond Blue enjoys an extraordinary, sublime view facing the bay. You can see Pinel and Saint Barth from the terrace, installed in a pleasant covered outdoor lounge The house, very pleasant and simple to live in, offers all the essentials for pleasant moments of relaxation.
Top guest favorite
An outdoor terrace features a sleek design with minimalist white seating arrangements and a shimmering pool. Tropical greenery frames the area, and expansive views of the ocean and sky create a serene backdrop. The layout encourages relaxation and enjoyment of the surrounding beauty.
Home in Collectivité de Saint-Martin
5 out of 5 average rating, 15 reviews

Prestigious Villa with Breathtaking Ocean View

DavidRating, 5 stars3 months ago
We had a fantastic time at Marion's house! She was amazing! The location is great - gated community between Grand Case and Marigot and not far from Orient Beach. The house was very clean and had everything we needed. View was amazing, pool and patio were nice (we spent a lot of time on the outdoor furniture), all the beds were super comfortable and the kitchen was very well equipped! Marion had some excellent dinner suggestions (even made our reservation for us at one place that was hard to get in) and she has a hook up with one of the beach restaurants at Orient that got us free chairs for the day. It might be worth noting that the house is a part of a 4-5 unit complex with neighbors on each side and a rental unit down below. However, this was not an issue as we rarely heard any of the neighbors and there is plenty of shrubbery and other elements that give adequate privacy. We even had a couples massage on the patio one day! Overall very pleased and highly recommend!!!
Guest favorite
A modern lap pool displays clear blue water reflecting the sky, bordered by a spacious deck. Two light blue chaise lounges are positioned nearby, accompanied by a large umbrella. The ocean and lush greenery form a picturesque backdrop under a partly cloudy sky.
Home in Blowing Point
5 out of 5 average rating, 7 reviews

Newly Renovated 2 Bedroom Villa

MarianneRating, 5 stars3 months ago
Aline and Katie were great to work with leading up to our trip. They looked into finding the best place for us to watch the Super Bowl (Go Birds!) and went on a shopping hunt to look for a thermos for the beach for us. Eli made our trip great!! He met us at the airport, led us to the villa, showed us around and had a welcome snack and beverage awaiting our arrival as well as the shopping list of groceries we asked for. Eli also arranged for us to get a Firestick to watch the Super Bowl in the comfort of our villa to watch the Eagles win! He checked in on us multiple times during our 9 night stay. The pool was the warmest of any we have rented in the Caribbean. The rooms were spacious and clean. Our only critique was that showers needed to be spaced apart for 4 people due to lack of hot water but it was manageable. Great stay!!!
Superhost
Home in Cole Bay
5 out of 5 average rating, 3 reviews

Luxurious Villa "Sea La Vie"

DavidRating, 5 stars2 months ago
Amazing spot on an amazing Island!
Guest favorite
A tranquil outdoor area features a clear infinity pool surrounded by lush tropical landscaping. Arched entryways lead to a covered patio with seating, while colorful flowers enhance the natural beauty of the space under a bright blue sky.
Home in Upper Prince's Quarter
5 out of 5 average rating, 17 reviews

"La Vue SXM" Paradise "Villa Rosa" 5 bedroom rate

ThomasRating, 5 stars3 weeks ago
Our stay for 8 people was wonderful. The area is more beautiful than imagined, and the pictures surely do not do it justice. The house is very private, and you need to traverse a couple large hills in order to get there. We had to swap out our first rental car because the tread felt very unsafe and struggled on some of the hills, but otherwise we really appreciated the privacy and sweeping views of the water from the villa.
Guest favorite
Home in Philipsburg
4.95 out of 5 average rating, 58 reviews

Villa Allamanda a Indigo Bay

AlenaRating, 5 stars3 months ago
Our stay was amazing! Props to the property manager, he was always there to help and responded super quick to any questions or concerns. Place was beautiful, although the pool was tiny it wasn't a huge deal. Only downside was that, during our stay, a mirror fell off the wall in the middle of the night and slightly shattered due to no fault of our own. My guess is it was hanging on something that broke... we were still asked to pay for the damages even though it was on them to better secure it to the wall. Other than that, great place and host! :)

Weekly house rentals

Guest favorite
A vibrant sunrise casts warm hues over the tranquil ocean, reflecting on the water's surface. Rocky cliffs frame the view, while distant islands are visible on the horizon amidst scattered clouds.
Home in Upper Prince's Quarter
4.88 out of 5 average rating, 34 reviews

Peaceful secluded 2BR apt w. sunrise & ocean views

KimberlyRating, 5 stars1 month ago
Adventurous and romantic! Exactly what we are looking for! It felt private despite the convenience of having the host nearby. Melissa was wonderful and very helpful. We sat on the patio and watched boats and cars and birds galore! There are some critters on the cliffs, like iguanas, but they won’t bother you. The breeze and air felt wonderful and I loved listening to the waves at night. I am very happy to chose to rent a Suzuki Jimny, as we observed other vehicles without 4x4 getting stuck on some nearby roads. It was exciting to see our cliff AirBnB from the catamaran tour we took. A lot of excursions go out of Bobby’s Marina, which is conveniently nearby and has secure parking for day trips. Trust the journey, the destination is beyond worth it!
Guest favorite
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
4.92 out of 5 average rating, 25 reviews

NEW House 2 bathrooms, 3 terraces and ocean view

ThandieRating, 5 stars2 weeks ago
Laurent was very helpful and friendly. The property was very nice and secure .
Top guest favorite
An outdoor dining area features a large wooden table set for a meal, with comfortable chairs surrounding it. The space is shaded by a wooden roof and white curtains, overlooking a pool surrounded by greenery. Glasses, plates, and a fruit centerpiece are arranged on the table.
Home in Oyster Pond
5 out of 5 average rating, 7 reviews

Spacious villa 8 people swimming pool sea view

ShaylaRating, 5 stars2 months ago
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!
Superhost
Sun loungers are positioned beside a clear pool, offering views of a lush, green hillside. The exterior design shows large sliding glass doors that open to a spacious living area, complemented by well-maintained landscaping.
Home in Mont vernon 3
4.67 out of 5 average rating, 3 reviews

Villa Carib sxm piscine.

AshantiRating, 5 stars12 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
Guest favorite
A serene outdoor area features a swimming pool surrounded by white stones. Comfortable lounge chairs are positioned nearby under palm trees. A dining table for six is set on the covered patio, providing an inviting space for meals and relaxation.
Home in Orient Bay
5 out of 5 average rating, 9 reviews

La Cool & Douce SXM, Orient Bay.

BrandonRating, 5 stars1 month ago
Virginie was the best host and you are paradise. It is the perfect location and had so many restaurants that we walked tomorrow throughout our trip. I would highly recommend!!
Top guest favorite
A private pool area features a clear blue swimming pool surrounded by a spacious patio. Lounge chairs are set beside the pool, while the bungalow's exterior is visible in the background, along with a dining set under an overhead structure. Lush greenery provides a natural backdrop.
Home in Collectivité de Saint-Martin
5 out of 5 average rating, 10 reviews

MAHI-MAHI Logde, private pool, Orient Bay

LennyRating, 5 stars2 months ago
It was one of the best spaces we ever rented via Airbnb. It is a perfect place for 2 adults, completely isolated and private. Pool a big plus. My wife and I are not a big fans of pools in general, but even we use it. It was close to all local restaurants and 5 min drive to supermarket. We already book it for the next year.
Guest favorite
An infinity pool and a lounge area are positioned on a deck overlooking the ocean. The pool features clear blue water, and the seating area is wrapped in bright blue cushions, providing a comfortable space to enjoy the expansive sea view under the clear sky.
Home in Upper Prince's Quarter
5 out of 5 average rating, 9 reviews

Sunrise & OceanView 3 bedroom Villa with Generator

NicolasRating, 5 stars3 months ago
This is a remarkable home and location. We could have stayed all day and soaked up the sun and views on the patio and in the lounge pool. The location is great to explore the island from. It is also quiet and peaceful. We decided to stay in the upper side of the island so getting to Orient Bay and Grand Case was a breeze. The home is within 15-20 minutes by car to some of the best restaurants we’ve ever been to. There’s also a great cafe within 10 minutes for coffee and pastries. Maia was very helpful and also taking advantage of the property concierge was very nice to get our trip started and help line up a few things for us. With two young children this was so perfect and the best vacation we’ve ever had!
Guest favorite
A private swimming pool is seen alongside a wooden deck, bordered by lush greenery and palm trees. Two lounge chairs are positioned for relaxation under the shade of a roof overhang, with outdoor dining furniture visible nearby, creating a seamless connection to the home's exterior.
Home in Anse Marcel
4.95 out of 5 average rating, 22 reviews

4 Clos de l'Anse - Anse Marcel

DeborahRating, 5 stars1 month ago
Julie’s place is a great spot in a quiet location near Anse Marcel beach. We loved the outdoor space and enjoyed cooling off in the pool.

Private house rentals

An outdoor dining area is featured alongside a private pool, with a clear view of the sea. A stone surface and neutral tones provide a contemporary backdrop. Lounge chairs are positioned by the pool, enhancing the inviting atmosphere.
Home in Lowlands
4.86 out of 5 average rating, 77 reviews

Sapphire Fantasy : Oceanfront paradise

ShavonaRating, 5 stars2 months ago
My stay at Smaart Vacation exceeded my expectations. Everything was as it was described on the booking site. The view was breathtaking! The property was in the perfect location. It was a lot to do in the area. I will book with them again in the near future. Look no further for a perfect stay in SXM.
Guest favorite
A charming yellow cottage is positioned near a sandy beach, surrounded by lush greenery. The structure features a corrugated metal roof and a small porch. A view of the water and distant boats can be seen in the background, creating a serene coastal atmosphere.
Home in Simpson Bay
5 out of 5 average rating, 13 reviews

Beach cottage in Simpson bay

BriannaRating, 5 stars1 month ago
Had a great stay! Location is amazing we are so grateful for this beautiful property to make our trip truly memorable!
Guest favorite
Steps leading down to a sandy beach are framed by a white railing. The clear turquoise water laps gently at the shore, revealing a mix of sand and smooth stones. Bright sunlight illuminates the tranquil scene, highlighting the serene coastal atmosphere.
Home in Cole Bay
5 out of 5 average rating, 12 reviews

Pelican key - BEACH FRONT Villa

JohnnyRating, 5 stars1 week ago
Alex’s place was great, it had a small private beach albeit a bit rocky. For adults that is good. For kids, there is a pool for them to play in. I would assume when the waves are a bit more calm it would be good for the kids to go in. Her house is also stocked with lots of kids toys so we were able to keep all the kids entertained while the adults lounge around. The one complaint I have is designated parking spots, the area has an abundance of street parking, but a few dedicated spots for the house would be nice. However this is not an issue with the house itself.
Top guest favorite
A spacious outdoor terrace features a stunning infinity pool overlooking the sea, complemented by comfortable sun loungers. A shaded dining area with a stylish table set for gatherings is visible, showcasing panoramic views of the coastline and vibrant blue ocean.
Home in Upper Prince's Quarter
5 out of 5 average rating, 5 reviews

Breathtaking view of St Barth – 8 people

ElizabethRating, 5 stars1 week ago
The home is luxurious and beautiful with stunning views and surroundings. The kitchen is fully equipped with everything you need and the space to dine is perfect for a family or group. There are so many sitting areas outside and in. The home is large with all rooms master size and facing the ocean. The decor is simple, classic and elegant! It was so easy to communicate and we had all our needs met. The hosts were amazing.
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
4.62 out of 5 average rating, 47 reviews

Villa Prospère

AmyRating, 5 stars1 month ago
The host was incredibly responsive and kind. The pool was amazing, and we thoroughly enjoyed our stay. It was within walking distance to the beach and restaurants, and only an 8-minute drive from the airport.
The villa is set amidst lush tropical landscaping, featuring vibrant flowers and palm trees. A spacious balcony offers seating areas with blue cushions, overlooking the vibrant garden. The light yellow exterior of the house complements the bright blue sky above.
Home in Cole Bay
5 out of 5 average rating, 3 reviews

Peaceful Paradise

BonnieRating, 5 stars3 months ago
Clark’s place was beautiful. It was spotless, modern, beautifully decorated, and well stocked with all the extras. There were four of us and we had lots of space. The beds were extremely comfortable and each room had its own bathroom. The grounds were stunning, with a pool and direct access to the ocean. Our favorite place was Clark’s deck that had the most incredible views of the gardens and ocean. We could have stayed there all day and night watching the boats, and the ever changing skyline, and sunsets. The location was very central and in a great area. It was within a few blocks (about 5-15 minute walk) to beaches, fun cafes, restaurants, and shops. It was an easy drive to main attractions on the island (e.g., Maho Beach, Orient Bay). Clark was an excellent host - very responsive and answered any questions that we had. We all loved our stay and would highly recommend it!
Guest favorite
A white gate opens to a sandy path leading to a turquoise ocean. Lush greenery frames the view, and a single tree stands on the left, creating a serene entryway to the beach.
Home in Simpson Bay
4.92 out of 5 average rating, 12 reviews

Coco's Beach House - Simpson Bay Beach

ClydeRating, 5 stars2 months ago
Really enjoyed the stay at this beautiful home. Peaceful love the sound of the ocean at night. Fun to watch the airplanes come by after landing and tiring around. The beach is beautiful and the privacy is second to none.
A spacious verandah features a comfortable seating area with a light-colored couch and a dark wicker coffee table. Lush greenery is displayed in a yellow planter, with panoramic views of the hills and bright blue sky in the background.
Home in Indigo Bay
4.77 out of 5 average rating, 155 reviews

La Pearle - Luxurious 1 Bedroom Condo By the Beach

MakiahRating, 5 stars5 days ago
This place was absolutely beautiful! It looked exactly like the pictures! I loved how responsive the host was during my stay! I would definitely stay again!

Quick stats about house rentals in Simpson Bay

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    600 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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