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Waterfront vacation rentals in Simpson Bay

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Popular amenities for Simpson Bay waterfront rentals

Waterfront apartment rentals

Guest favorite
The open dining area features a round table set for six, accompanied by wooden chairs and decorative centerpieces. Soft lighting from pendant fixtures enhances the inviting ambiance. A comfortable seating area with a plush sofa and contemporary artwork completes the stylish layout, along with large windows providing natural light.
Apartment in Cupecoy
4.91 out of 5 average rating, 11 reviews

Designers Delight-3 BR, Pool, Gym, Tennis Courts

CrystalRating, 5 stars1 month ago
Property exceeded my expectations. Even better in person than the pics. The location was ideal and perfect for the 6 of us. We were so comfortable in the condo. Very spacious, well appointed and super walkable. Enzo was a gem. Very responsive and super proactive with recommendations. Can not say enough about how much we enjoyed this rental. Will definitely return.
Top guest favorite
The living area features floor-to-ceiling windows offering panoramic views of the lagoon and mountains. A comfortable blue sofa is complemented by textured cushions, with a cozy brown armchair nearby. A round table sits in the center, showcasing a remote control and decorative elements.
Apartment in Lowlands
5 out of 5 average rating, 46 reviews

Gorgeous 2 bedroom-17th floor, Fourteen Mullet Bay

KilmaRating, 5 stars2 weeks ago
Tamara was such a sweet and responsive host, she made everything seamless from start to finish. The unit was even better in person: super spacious, spotless, and the view was absolutely incredible. We felt right at home with how well-stocked everything was, from toiletries to detergent to coffee. The building amenities were clean and easy to access, and we especially loved the restaurant by the pool, perfect for lazy breakfasts without leaving the property. The staff onsite were warm and welcoming, and we felt completely safe the entire time. I would 100% stay here again. Thank you for an amazing stay, Tamara!
Guest favorite
A comfortable outdoor seating area is featured, consisting of a white sectional sofa and individual chairs, all accented with red cushions. A small table sits in the center, surrounded by lush greenery and a view of the beach in the background.
Apartment in SAINT MARTIN
5 out of 5 average rating, 15 reviews

"Black Pearl"

ShaunaRating, 5 stars1 month ago
We had a great stay. The unit is even better than in the photos. We encountered a few maintenance issues but host was quick to respond. Stephanie was always reachable and very helpful. The resort grounds are beautiful. Would stay again.
Top guest favorite
A bright area is designed with a spacious window offering views of palm trees and the beach. Three wicker bar stools are positioned at a counter, alongside a minimalistic desk lamp. The room features a light color palette with wood flooring and a cozy bed partially visible.
Apartment in Marigot
5 out of 5 average rating, 13 reviews

Studio Coconut

Esther-JoyRating, 5 stars3 weeks ago
If you’re looking for a quiet place to relax and unwind this place is for you. It’s on a beach but the waters weren’t so calm so I didn’t want to take the chance. Lola is very hospitable & was very responsive and helpful before and after arriving. The studio is just as seen in photos, very clean and has a modern cozy vibe. I’d suggest you rent a car…Lola helped with that before I arrived so I was able to pick up the car at the airport. I think this is a great option for a solo traveler as well.
Superhost
A spacious living area features contemporary furnishings, including white sofas and an accent chair, accompanied by a decorative coffee table. A striking mural of a cityscape adds visual interest. Natural light fills the room, enhancing the open layout leading into the dining area.
Apartment in Simpson Bay
4.86 out of 5 average rating, 21 reviews

Escape by the Lagoon

DianaRating, 5 stars1 month ago
Home was exactly as described with an amazing host!! Thank you for making my birthday special.
Top guest favorite
A contemporary living area showcases a spacious white sectional sofa paired with wooden accent tables. Large windows frame a scenic sea view and allow natural light to illuminate the space. A sleek entertainment unit holds a flat-screen TV, and a stylish ceiling fan enhances comfort.
Apartment in Lowlands
5 out of 5 average rating, 12 reviews

Luxury apartment, sea view

GabeRating, 5 stars1 month ago
The pictures of the condo unit were EXACTLY as they were advertised on this site. The Condo was in Excellent condition. They complex where the unit is located is a wonderful with location that is in the heart of the Cupecoy area of the island. The host was very accommodating and answered important questions prior to us booking. The service we received upon arrival was equally outstanding and responsive. The overall experience was Excellent. The combination of location, the complex, the unit and host all added up to be one of the best units we have rented on this platform, to date. I would 100% recommend this location and the unit to anyone who wants an amazing place to stay in St. Maarten. It is a perfectly located spot on the island. We'll be back for sure! Thanks
Guest favorite
A bright living space features large glass doors that provide a view of palm trees and the nearby beach. A dining table with four chairs is situated near the windows, and a cozy sofa enhances the relaxed atmosphere. Natural light fills the room, creating an open feel.
Apartment in Philipsburg
4.92 out of 5 average rating, 117 reviews

Amazing "Colosseo" duplex ocean view

AlexandriaRating, 5 stars1 week ago
This is such a beautiful property, the view is breathtaking. Leda was very helpful, and responsive any and everytime I needed her. You won't be disappointed ❤️
Top guest favorite
The infinity pool is visibly stretching towards the horizon, blending with the calm turquoise waters of the Caribbean Sea. Palm trees frame the scene, while a cruise ship can be seen cruising in the distance under a clear blue sky.
Apartment in Philipsburg
5 out of 5 average rating, 16 reviews

Studio Ocean Front, Infinity Pool

MattRating, 5 stars1 month ago
Michelle and Brent’s spot is absolutely perfect for a couple. You have a beautiful view of the ocean right outside the doors. This is one of 3 villas she has on the property. This studio is below a 2 bedroom space that you share the infinity pool with. I can’t wait to come back and stay with them. The location was perfect and a quick ride to everything on the island. 10/10 would recommend 🤌🤌🤌

Waterfront house rentals

Guest favorite
Two blue lounge chairs are positioned on a sandy beach, facing the turquoise sea. Gentle waves can be seen lapping at the shore, with green mountains visible in the background under a clear blue sky.
Home in Collectivity of Saint Martin
4.96 out of 5 average rating, 46 reviews

New! On the beach, 2 bedroom villa, sea view, pool

SueRating, 5 stars3 months ago
It was lovely to watch the waves and listen to the ocean everyday from our patio. Laure was so welcoming and offered ideas for places to go during our 6 week stay. She was very responsive to messages from us and genuinely want to make sure we had a wonderful visit. We were close to a variety of cafes and restaurants. The French bakery was a wonderful morning walk and Boat On Yacht Club a charming afternoon excursion. It took us a short time to get used to the to driving in Marigot but by the second week, we were comfortable with our route. I recommend getting out and about throughout the island. There is plenty to explore! Laure is a gem! We would stay here again.
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
A serene outdoor area features a heated swimming pool surrounded by comfortable loungers. Lush tropical plants and palm trees frame the space, while scenic views of the bay and ocean are visible in the background under a clear blue sky.
Home in Les Terrasses de Cul de Sac
4.95 out of 5 average rating, 21 reviews

Water access, heated pool, kayaks & snorkeling

HilaryRating, 5 stars1 week ago
We had an excellent week at Villa Cote Mer! I honestly can’t say enough good things. It is better than described. Pictures don’t even do it justice. It is very private and quiet, with a gorgeous view. There are plenty of places to eat within a 10 minute drive. Grocery store is less than 5 minutes. Melissa and Nina have provided a helpful guide to area restaurants, shops, and other attractions that make it so easy. The place was spotless, and the pool was pristine. It was very nice having midweek cleaning with fresh towels and linens. The garden area is gorgeous with many beautiful trees, flowers, and native foliage. The house sits down some from the road making it even more private. We have stayed in many Air BnBs in several international locations, and this one is one of the best! Melissa and Nina have been incredibly responsive and communicative making this a seamless, easy vacation. We will definitely stay here again the next time we visit St. Martin!
Top guest favorite
A modern pool area is positioned by the ocean, featuring a clear blue water pool and two sun loungers. A potted palm adds a tropical touch, with the horizon visible beyond gentle waves and scattered clouds.
Home in Cole Bay
5 out of 5 average rating, 20 reviews

New-Sunset Place Villa w Stunning Waterfront Views

DanaRating, 5 stars2 weeks ago
The villa was perfect. Beautiful view, upscale and clean. Joy was easy to communicate with and offered help with logistics such as car service private yachts, groceries and private chef service. The private pool off our deck was clean and refreshing We started planning our next trip before this one ended.
Superhost
The villa is presented from an elevated angle, showcasing a private pool surrounded by a sleek patio. Large glass doors provide a view of the inviting interior, while sun loungers are placed alongside the pool, integrating seamlessly with the lush surroundings.
Home in Lowlands
4.72 out of 5 average rating, 113 reviews

SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay

EmmanuelRating, 5 stars1 month ago
An amazing place even better in person
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!!!
Top guest favorite
A shaded outdoor seating area features a comfortable sectional sofa and a natural wood coffee table. Tropical palm trees and a view of the pool enhance the space, while loungers are positioned nearby. Soft textiles in muted colors contribute to a laid-back ambiance.
Home in SAINT MARTIN
5 out of 5 average rating, 14 reviews

The best view on the island!

LeslieRating, 5 stars3 days ago
Casa Victoire is one of the best rentals we have ever used for vacation- the pictures do not do it justice and Maly was an amazing host! If you are thinking about staying here just go ahead and click that button and you will not be disappointed. The pool was fabulous overlooking the bay and Pinel Island. Within a few minutes drive of Grand Case and Orient Bay- both with plenty of activities and food. Maly provided so much useful information before arrival and during our stay. The layout worked great for myself and 4 adult children- plenty of space for all. If you rent a car I highly recommend Nono car rental recommended by Maly- car will be waiting on you at the house and they will pick you up at the airport so you can get right to your vacation without worrying about driving as soon as you arrive Thank you Maly- we look forward to our next trip to St Martin!
Guest favorite
An open-plan living area is showcased, featuring large glass windows that frame stunning ocean views. A modern kitchen with a sleek island counter is visible alongside a cozy seating area with two brown sofas. Natural light fills the space, creating a welcoming ambiance.
Home in Upper Prince's Quarter
4.96 out of 5 average rating, 45 reviews

Teresa’s Ocean Paradise

EleishaRating, 5 stars4 days ago
Marcus & Jocelyn’s place was extremely nice. The location is about 30 mins from the airport which allowed us to view more of the island. The place was extremely nice, quiet and the view is beautiful. Irene the host was very friendly and provided treats at check in. The home was stocked with plenty of refreshments which was very thoughtful. I truly enjoyed my stay.

Waterfront condo rentals

Superhost
A spacious bed is positioned against a wall adorned with a vibrant tropical painting featuring flamingos. Soft lighting is provided by two wall-mounted fixtures on either side, complemented by decorative plants and towels laid out for a welcoming touch.
Condo in Marigot
4.85 out of 5 average rating, 136 reviews

Comfort & Charm – Premium Studio

NaomiRating, 5 stars1 week ago
Thank you Aurelien. We really were so comfortable at your place and admired the cute and clean style! We will recommend your place to friends snd family
Guest favorite
A spacious bedroom showcases a comfortable bed with neutral linens and several decorative pillows. Floor-to-ceiling glass doors open to a private balcony with seating, offering views of the ocean and the surrounding landscape. Soft lighting is provided by two bedside lamps.
Condo in Lowlands
4.93 out of 5 average rating, 14 reviews

Modern Oceanview Apartment

CarolinaRating, 5 stars1 month ago
Incredible location, clean unit and building, literally a 5min walk to mullet bay beach, 5min walk to Cupecoy beach, and two grocery stores one right next door to the building the other just a 3min walk away and two good cafes. Host was available and quick to respond to any needs, i will definitely be booking this unit again! Thank you
Top guest favorite
Two sun loungers are positioned on a sandy beach, accompanied by a small table holding a bottle of champagne and two glasses. A backdrop of clear blue water and gentle waves is visible, with a few green trees enhancing the tranquil setting.
Condo in Saint Martin,Guadeloupe
5 out of 5 average rating, 47 reviews

Villa Belharra, amazing view

ChantalRating, 5 stars1 month ago
We were amazed by this rental. We’ve always had great ones in the past but this one is the most beautiful one we’ve had. Rachel and her husband were amazing people and are taking care of your needs as soon as you get there. The views you have from the patio is amazing and relaxing. We will return for sure.
Guest favorite
A living area features a modern television mounted on a minimalist white console. A circular coffee table sits below, accompanied by a decorative shell. Light filters through sheer curtains, illuminating the space and offering a glimpse of the outdoor area.
Condo in Marigot
4.93 out of 5 average rating, 46 reviews

Beachfront Condo| Pool View + Private Beach Access

SarahRating, 5 stars1 week ago
We loved everything about our stay! Beach is right in your backyard and Marigot is within walking distance. Will definitely be staying here again in the future!
Top guest favorite
An aircraft descends just above a vibrant beach, with visitors enjoying the sun and clear blue waters. Tropical palms line the foreground, while sandy shores are dotted with colorful umbrellas and lounge chairs. A well-maintained resort can be seen in the background.
Condo in Sint Maarten
4.96 out of 5 average rating, 80 reviews

FLASH SALE! June-Oct. 2025! Ocean&Tropical Views!

DennisRating, 5 stars1 month ago
This location is excellent ..everything is near by ..the host is amazing ...thank you for everything its definitely worth it...I wiill be back again and again
Superhost
A spacious terrace is visible, featuring a wooden dining table surrounded by black chairs. A hanging rattan chair offers a cozy seating option. Lush palm trees and a serene lagoon can be seen in the background under a partially cloudy sky.
Condo in Marigot
4.71 out of 5 average rating, 84 reviews

BLUE JUNGLE♡ Duplex Terrace Amazing Sea View

JackRating, 5 stars2 weeks ago
The two of us had a wonderful long-weekend getaway! The unit and surrounding property is absolutely stunning. We loved the modern touch of the unit and how clean everything is. We got way more than we paid for and I’m so thankful we discovered this property.
Guest favorite
A spacious living area features large windows showcasing a view of palm trees and the lagoon. A wooden dining table is set for six, and an inviting seating area is arranged with a light-colored couch and coffee table, enhancing the serene ambiance.
Condo in Cole Bay
5 out of 5 average rating, 15 reviews

Sea Lover - Las Brisas (Sea Lover)

MarkoRating, 5 stars4 months ago
Thank you so much. We enjoyed it.very comfortable to stay with kids.
Guest favorite
A serene beach scene is presented with four lounge chairs under two sun umbrellas, offering shade. Soft sandy ground surrounds the area, with tropical palm trees in the background. The clear blue sky adds to the tranquil atmosphere, inviting relaxation by the beachfront.
Condo in Simpson Bay
4.89 out of 5 average rating, 9 reviews

*NEW* Coco's 15 Modern beachfront Retreat

KatrinaRating, 5 stars1 month ago
The place was steps from the beach! Beautiful and clean. Host very helpful. We loved st. Martin and this family friendly beach next to Mary Boons! We ate lunch there and cooked in dinner at home. Great appliances And every cooking tool you could need. Andrea was very helpful. The only thing I was a little worried about was the airplanes noise and honestly you forget they are even there after first day.

Quick stats about waterfront rentals in Simpson Bay

  • Total rentals

    130 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 before taxes and fees

  • Total number of reviews

    4.8K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    90 properties have a pool

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