
Vacation rentals in Simpson Bay
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Top-rated vacation rentals in Simpson Bay
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Popular amenities for Simpson Bay vacation rentals
Simpson Bay oceanfront vacation rentals

Modern Cozy Stay Steps From Mullet Beach
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

Water access, snorkeling gear & kayaks
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!

Lilly's Beach
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.

RIGHT ON ORIENT BEACH Oceanview Garden Suite 4* 🏝🌞
Wonderful week in paradise ! Great hosts !

Enjoy Stunning Sunsets Beachside 2 BR/2 Bath Condo
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.

Fayalobi - Large 1 bed Beachfront Apt 2nd floor
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!

2 Bedroom Ocean Front Villa, Private Infinity Pool
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.

Top floor, incredible view on ocean and Orient Bay
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

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

Villa 2 Chambres Indigo Bay
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!!!

Casalinda Amazing Sunsets Pelican Key St Maarten
absolutely amazing! gorgeous views, very clean, host is super super nice and helpful would 10/10 recommend!

Tropical Getaway Sxm!
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.

Villa with sea view and heated pool
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!

Infinity Views Indigo Bay SXM
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

Sugarbird Nest: Sunrise Ocean Views | Great Bay
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.

Mountain View
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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