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Vacation rentals in Simpson Bay

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Simpson Bay vacation rentals

Stay near Simpson Bay's top sights

Maho Beach72 locals recommend
Carrefour Market, Sint Maarten61 locals recommend
Karakter Beach Bar/Restaurant48 locals recommend
Avantika36 locals recommend
Soggy Dollar Bar31 locals recommend
The RedPiano Lounge29 locals recommend

Simpson Bay oceanfront vacation rentals

Guest favorite
A well-lit bedroom features a spacious bed adorned with a colorful patterned quilt. Large glass doors open to a balcony, offering views of the surrounding area. Light-colored walls and stylish furniture contribute to the room's contemporary look.
Apartment in Lowlands
5 out of 5 average rating, 5 reviews

Modern Cozy Stay Steps From Mullet Beach

HoueRating, 5 stars1 month ago
Very nice place. good location, as described. Very pleasant stay. Only small downside: the TV was not working. We'll be back! Thanks to Golden Palm
Top guest favorite
A bright living area features a comfortable sofa and a wooden coffee table, with natural light flowing in through large sliding doors. The space is complemented by woven light fixtures and a decorative wall hanging, offering views of the outdoor seating and lush surroundings.
Home in Cul-de-Sac
5 out of 5 average rating, 42 reviews

Water access, snorkeling gear & kayaks

MonicaRating, 5 stars2 months ago
Our stay at this Airbnb in St. Martin was incredible! The place was exactly as described and looked just like the photos—beautiful, clean, and well-stocked with everything we needed. The hosts were fantastic—super responsive and even helped us coordinate in-house massages, which was such a treat. One of the highlights was the kayaks, which we highly recommend using to visit Pinel Island—an unforgettable experience! This rental truly exceeded our expectations, and we wouldn’t hesitate to stay here again if we return to the island. Highly recommend!
Guest favorite
A dining area features a modern table with four chairs, positioned near large windows showcasing panoramic views of the turquoise sea and sandy beach. A wall mirror reflects the inviting atmosphere, while lush greenery can be seen outside, enhancing the coastal ambiance.
Apartment in Simpson Bay
4.96 out of 5 average rating, 193 reviews

Lilly's Beach

JennaRating, 5 stars3 weeks ago
Great, private location with beautiful views while still being walking distance (20ish min) from the main strip. The walk to the strip is through some run down areas but felt safe and walked to and from every night with no concern. Beach access & beach chairs easily accessible and found everything we needed for an easy stay. I would recommend a rental car to visit other parts of the island. Airplane noise was no issue as it’s only prevalent during daytime hours. Would stay again.
Superhost
A dining area is set outside, featuring a wooden table with seating for four. Lush greenery surrounds the space, offering a view of the turquoise ocean beyond. The scene highlights the tranquil beach atmosphere, with gentle waves visible in the distance.
Condo in saint martin
5 out of 5 average rating, 4 reviews

RIGHT ON ORIENT BEACH Oceanview Garden Suite 4* 🏝🌞

RobynRating, 5 stars13 months ago
Wonderful week in paradise ! Great hosts !
Guest favorite
A circular pool glistens under clear blue skies, surrounded by a sunbathing area with lounge chairs. Lush greenery lines the pool, leading toward the turquoise ocean in the distance, while gentle waves can be seen lapping at the shore.
Condo in Lowlands
4.94 out of 5 average rating, 32 reviews

Enjoy Stunning Sunsets Beachside 2 BR/2 Bath Condo

JodyRating, 5 stars1 month ago
Kevin's condo was great met all of our needs. Was clean and comfortable. Plenty of hanger and shelf space. We were 2 couples, plenty of room for together and alone time. Two en suit bathrooms for privacy. Great views, close to pools, and a short walk to beaches, restaurants and grocery stores. Everyone including staff and other owners were extremely friendly and informative. Kevin was a great host. Quick to reply an answered all questions. Would highly recommend to friends and family. Great place to stay.
Guest favorite
A covered balcony features a view of a sandy beach and mountainous landscape in the distance. Lush greenery is positioned nearby, and the space is illuminated by natural light filtering through the open area.
Apartment in Philipsburg
5 out of 5 average rating, 11 reviews

Fayalobi - Large 1 bed Beachfront Apt 2nd floor

LoanRating, 5 stars3 weeks ago
One of the top Airbnbs we’ve stayed at! Well air conditioned, spacious, great views, and great amenities - huge walk-in closet, second bathroom was a plus, and washer/dryer, dishwasher are state of the art. We had no troubles parking in the area thanks to Ludmila providing an area to park. Airbnb is in a prime location on Front St and very accessible to restaurants, shops, taxis. The place still felt private and safe for two young ladies. Also, Ludmila is the best host! She was very responsive and went above and beyond to make our stay comfortable. Loved her! A few restaurants we loved nearby: Simple Tingz (Jamaican Indian), Jimmys Original Fat Boy BBQ, Chez Delphine, and Coffee Lounge. Bobby’s Marina is nearby, which was convenient because we walked over to meet Under SXM for our snorkeling tour of the underwater sculpture park. A must! I highly recommend booking this place!
Top guest favorite
A refreshing pool area is surrounded by palm trees and colorful tropical plants. Lounge chairs are positioned near the pool, offering views of the turquoise Caribbean Sea and nearby coastline. Natural light illuminates the space, emphasizing the vibrant outdoor environment.
Home in Philipsburg
5 out of 5 average rating, 17 reviews

2 Bedroom Ocean Front Villa, Private Infinity Pool

BillRating, 5 stars4 weeks ago
Michelle was an incredible host! She met us upon arrival and made sure we were comfortable and knew all the ins and outs of the villa. The place was exactly as pictured—absolutely gorgeous, with a breathtaking view! She had placed a very thoughtful gift basket out for us, along with recommendations for dining, shopping etc. The home was immaculate…and very well appointed…perhaps the best Airbnb kitchen setup I’ve seen…every time we thought, “I wonder if they have a….” The answer was yes! You could tell that Michelle is very detail oriented from how thoughtfully laid out everything was. And throughout the stay, they were very friendly and communicative, helping us with any questions we had or just being friendly and gracious hosts. This home is a multi unit villa enclosed by a gate and a wall; so Michelle and her husband live next door, but you would never know they were there—it feels very secluded and peaceful. The location is perfect…close to everything.
Superhost
An open living area features a comfortable sofa positioned beside a side table with a lamp. A round dining table with wooden chairs stands on the terrace, offering unobstructed views of the ocean and horizon through large glass sliding doors.
Condo in Étang Chevrise
4.74 out of 5 average rating, 27 reviews

Top floor, incredible view on ocean and Orient Bay

DylanRating, 5 stars2 weeks ago
I had a fantastic stay at Laurent’s Mont Vernon Airbnb right at the top of the Orient Bay beach in Saint Martin. The Airbnb was spacious and clean and looked exactly like the photos- you truly can’t beat the view on the balcony! Once you walk down the steps of the compound to the beach (because it is such a large beach) it is about a 10-15 minute stroll until you reach the start of the beach clubs and Orient Bay Village. Laurent was also a very responsive host on the Airbnb app as well as text communication to answer any questions I had. Highly recommend staying here!

Other great vacation rentals in Simpson Bay

Top guest favorite
Villa in Cul-de-Sac
5 out of 5 average rating, 19 reviews

Villa Pure - 3 BR waterfront with kayaks, wifi, AC

StaciRating, 5 stars1 week ago
Villa Pure was far and away the nicest Airbnb we have ever stayed in. The property genuinely exceeded every expectation. Beautifully and comfortably furnished with everything we could possibly need. The outdoor space was sprawling and private and was an amazing second living space with beautiful views. The beds were so comfortable too. The hosts were communicative and offered suggestions and recommendations to any requests or questions we had. It was a great location, so close to Super U (Grocery), Orient Beach, Grand Case, but maybe the most special is that it's right across from Pinel Island that we Kayaked to twice to enjoy the restaurants and the secluded atmosphere. Our kids spent every morning hunting for beautiful shells, days in the pool, playing volleyball, ping pong all in our backyard. I cannot recommend this place enough! We can't wait to come back next year
Superhost
A modern kitchen is equipped with sleek cabinetry and contemporary appliances. A white countertop extends into a dining area with three black stools. Large glass doors open to a grassy outdoor space, providing a view of the pool area and distant water.
Home in Sint Maarten
4.67 out of 5 average rating, 12 reviews

Villa 2 Chambres Indigo Bay

JefferyRating, 5 stars1 month ago
Phadya and Robert's "Oceans 29 " was everything that was advertised, beautiful, clean, contemporary with a great central location and breath taking views !!! Check-in was easy with Phadya describing all the Villa amenities and some ins and outs of the property. We would definitely stay here again and will recommend to future Sint Maarteen visitors!!!
Superhost
The bright living area features a comfortable seating arrangement with white sofas and a wooden coffee table. Large sliding doors open to a view of the outdoors, allowing natural light to fill the space. A dining area is visible in the background.
Home in Cole Bay
4.88 out of 5 average rating, 8 reviews

Casalinda Amazing Sunsets Pelican Key St Maarten

EmmaRating, 5 stars1 month ago
absolutely amazing! gorgeous views, very clean, host is super super nice and helpful would 10/10 recommend!
Superhost
A private pool is situated on a spacious terrace, with sun loungers placed around its edges. The surrounding hills provide a lush green backdrop, while a covered seating area is visible to one side, offering shade and comfort for relaxation.
Apartment in DUTCH CUL DE SAC
5 out of 5 average rating, 3 reviews

Tropical Getaway Sxm!

ShadyraRating, 5 stars2 months ago
We had a very pleasant stay. The place is spacious and had everything we needed. The environment is great if you come as a group, where you can entertain together but also everyone has their private space. Brandon was a very accessible host. the place was well situated and next time if I am coming with a group I would definitely stay at his place.
Superhost
A serene swimming pool with clear blue water is framed by lush greenery. Two turquoise lounge chairs are positioned beside the pool, offering a relaxed spot to enjoy the tranquil view of the Caribbean Sea in the background under a bright blue sky.
Villa in Saint-Martin
5 out of 5 average rating, 3 reviews

Villa with sea view and heated pool

JaniqueRating, 5 stars14 months ago
We absolutely loved staying at this villa for many reasons. First, its location and three features we appreciated: it is on the west side of the island which means we saw beautiful sunsets every night; it is near Friar’s Bay Beach that we enjoyed a lot, including delicious food and great music at the Friar Bay Beach Café (quick note: you can walk to Friar’s Bay through the road - probably a 10 mins walk - but with the heat, we preferred to drive); and finally, it is secure and very private - we did not see nor hear neighbours. Second, its comfort. We spent most of our time outside, either in the pool or the covered patio. We also made friends with the turtles! The villa is well equipped with all we needed. And I would be remiss not to mention Julia’s quality service. She welcomed us at the villa and was very efficient to explain all its features. It was easy to communicate with her. Merci Julia!
Superhost
Colorful bougainvillea flowers frame a stunning ocean view filled with sailboats on the horizon. The bright blue waters and varied shades of the sky highlight the vibrant scenery, creating a serene coastal atmosphere.
Villa in Indigo Bay
4.82 out of 5 average rating, 49 reviews

Infinity Views Indigo Bay SXM

KingRating, 5 stars3 weeks ago
This property had an excellent location. Very peaceful, relaxing, and not far from many restaurants and experiences. Host was always responsive and had very clear instructions for everything. I would definitely stay here again! 10/10
Guest favorite
A panoramic view of the southeastern coastline featuring calm turquoise waters and a distant hillside. Boats are anchored in the harbor, with the outlines of the shore and hills providing a tranquil backdrop under an overcast sky.
Villa in Little Bay
4.96 out of 5 average rating, 46 reviews

Sugarbird Nest: Sunrise Ocean Views | Great Bay

BrendaRating, 5 stars1 month ago
Sugarbird Nest was an absolutely wonderful place to stay. During our 2 week holiday Ariana was always available to offer suggestions on places to visit on the island, and restaurants to eat. We really enjoyed walking into Philipsburg and watching the cruise ships come and go. Our view of Great Bay and Divi Little Bay was wonderful. Fiona and Bobby were great animals “hosts” as well. The pictures shown are exactly like it is, and the space was bigger than we expected. There were so many great amenities. We highly recommend this Airbnb. We will be back.
Top guest favorite
Villa in Lower Prince's Quarter
5 out of 5 average rating, 24 reviews

Mountain View

KimRating, 5 stars2 weeks ago
Nick’s was the perfect place to unwind after a long day of traveling! It was cozy, comfy and very clean! We were really impressed how much Nick communicated with us and made sure we had what we need.

Quick stats about vacation rentals in Simpson Bay

  • Total rentals

    340 properties

  • Nightly prices starting at

    $30 before taxes and fees

  • Total number of reviews

    10K reviews

  • Family-friendly rentals

    150 properties are a good fit for families

  • Pet-friendly rentals

    60 properties allow pets

  • Rentals with a pool

    230 properties have a pool

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Simpson Bay?

    Yes! Work meets play with ease at over 140 vacation rentals in Simpson Bay featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in apartment rentals in Simpson Bay?

    Experience the best of Simpson Bay with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Simpson Bay?

    Four-legged friends are welcome in Simpson Bay. Choose from more than 60 vacation rentals for guests traveling with pets.

  • Are there Simpson Bay vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 230 vacation homes with pools in Simpson Bay, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in Simpson Bay have self check-in?

    Absolutely! We offer over 20 apartment rentals with self check-in in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Simpson Bay have a bbq area?

    Absolutely! We offer over 20 house rentals with a bbq area in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Simpson Bay have wifi?

    Absolutely! We offer over 30 villa rentals with wifi in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Simpson Bay have a gym?

    Absolutely! We offer over 50 condo rentals with a gym in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly condo rentals in Simpson Bay?

    Simpson Bay has more than 50 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Simpson Bay?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

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