
Condo vacation rentals in Simpson Bay
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Top-rated condo rentals in Simpson Bay
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Popular amenities for Simpson Bay condo rentals
Weekly condo rentals

Janel's Gem - Lovely 2- bdr condo in Weymouth Hill
I would recommend this accommodation. It was a really great experience. He was so helpful and always reachable when you had questions.

FLASH SALE! June-Sept. 2025! Ocean&Tropical Views!
Wonderful location in Simpson Bay. It is walking accessible to everything in the area.

Vacation in Paradise on the Beach
The photos, description and previous reviews are very accurate and reflect reality. Big favorite for the terrace and for the decor of the studio. Patrick is a perfect host! The Mezza Luna and Savannah restaurants within walking distance are delicious, as well as the nearby bakery for croissants, sandwiches and coffee. We would recommend this studio without hesitation, perfect for a couple or single person.

Isla 517, Cupecoy, St. Maarten
Great spot! Safe, friendly people. We liked the pool option too. The rooftop is extra special at sunset if you come back from the beach early; also a quiet place to read. Certainly a fabulous location for bakery, cafes, restaurants, groceries and exquisite beaches. Super convenient & walkable. Good parking too. Shelly was warm, helpful and replied quickly before & during our trip.

Grand Getaway - Royal Retreats at Maho Beach Studi
Great location! Grocery store and many restaurants are all on the same strip in walkable distance!! Left plenty of necessities like towels, wash clothes, toilet paper and dish soap. Over all great place to stay!!

On the beach beautiful one bedroom 2 baths
Marie’s place came as advertised. It was clean, spacious, functional, cozy, and well decorated. The kitchen and bathrooms were well equipped and generally in good working condition. The water in the master bath shower ran a bit cooler than the main bath shower but not a huge issue as there was thankfully the second bathroom as an option. The view and proximity to the beach was appreciated daily and was a differentiator. Didn’t swim in it though as there are better options nearby but was essential to our overall experience. Parking was really convenient too. The location is very close walking distance to a small grocery store (literally across the street) and an awesome boulangerie (we bought quality baguettes and pastries there daily). Marie was very friendly, kind, helpful, and quick to respond to your needs. Overall, it checked off on everything we expected and was a key factor to making our vacation a success. Would definitely come back!

Paradis Caraibes 2BR * On the Beach!
The setting and location of this apartment is outstanding. It was wonderful to be able to see the sea out the window, hang out on the patio, and walk right down a few stairs to the beach. It is a 5 minute walk down the beach to the beginning of the town with tons of restaurants, I understand some of the best on the island. We liked being away from the busier parts of the island where the cruise ship ports are. A couple downsides of the the apartment is that you hear people pretty easily because oddly the bathrooms have windows that go to the common areas, I guess for ventilation, but it can be noisy and we heard babies cry in the middle of the night. A sound machine could be a good option. The other potential downside is being on a busy road without a sidewalk. We were close to town but didn't want to walk on the beach at night, so ended up driving. Though there are not many parking spaces, Ian did tell us where else to park when the spaces were full and that worked out.

Beachfront 3 bedroom apartment on Simpson Bay
This was my 7th visit to St. Maarten and I would absolutely stay at this beautiful condo again. It is spacious and clean and the location on Simpson Bay can't be beat. Check-in was a breeze and the host provided a welcome basket on our arrival that allowed us to put of shopping for groceries until the next day -- so we were able to hit the beach immediately. I love that we could walk to lots of bars and restaurants, as well as walk to beach clubs with the closet being right next door. Great property and great host!! If you're on the fence about this one - don't be - you're going to LOVE it!
Pet-friendly condo rentals

Feet in the ocean, Orient Bay, Beach apartment
We absolutely loved our stay and hope to be back! Virginie thought of everything international travelers might need for a beach getaway from the beach chairs, table, and cooler to helpful directions and welcome notes. You can’t beat the convenience to the beach and the pool was an added bonus when the beach got too crowded on big cruise ship afternoons. Highly recommend booking!

Modern Oceanview Apartment
The apartment is a perfect size for a couple with a large balcony and a breathtaking view. When we had questions and concerns Anna and Ash were available for help. All in all a great vacation. The only thing that worth mentioning that TV was not working but it actually made us spend more time outside and in the sun 🌞😀

"SeaBird" studio, feet in the water on the beach
I highly recommend booking Camille's place. She was very responsive and made checking in very easy. Her place has an amazing view and is a short walk from several great restaurants.

Luxurious apartment, direct beach access
Jean Pierre is kind and helpful. helped me to carry the luggages upon check in and check out. The entrance is on a beach and have some stairs which would have been difficult without the help of Jean Pierre! the place is modern and well furnished and have everything you need. the view is spectacular and the beach is right in front so you can hear the sound of the sea while in the apartment. I love that! Its perfect for one person or a couple and I will be back again to my lovely St.Maarten and stay at this place if its available.

Casa Nova, Indigo Bay SXM
Beautiful accommodations, exactly as shown in the pictures. Indigo Bay is a lovely site, peaceful, serene yet close enough to plenty of action in town. Wonderful host and very helpful with recommended activities and check in was a breeze. Great value for the money. Would definitely return to this air bnb!

Cozy Duplex 5, Le Shamrock Orient Bay Residence
The house is just like the photos, a common area with a pool, barbecue and a beautiful garden. The cleaning is excellent. It has everything you need to use in the kitchen. You can feel at home. The hosts are super attentive and are aware of everything. Thanks!

Modern / cosy Studio next to university / Beach
Laurent's unit was exactly as described and pictured. It is a small, efficiency unit designed for 2. In is located in the heart of Jordan Village which can be busy with college students during the day and some bustle at local restaurants at night, so I was pleasantly surprised how quiet the apartment was. It is only yards from the Carrefour grocery and numerous restaurants and an easy walk to Mullet Bay. Check in was very simple and Gwen was quick with communication. We would recommend to singles or a couple looking for a clean and modern efficiency apartment at a good price.

Duplex Frangipani Sea view and Saint Barth
This Airbnb and a very good value. It was clean and the downstairs air conditioner was cold when we needed it. The views are spectacular! Karine was quick to help us out when we needed bowls and beach towels. She helped us with the WiFi and upstairs fan too. Ask her for directions to the path to Orient Beach. The pool is on the ground floor-it’s not obvious from the photos-and sometimes it was busy with up to 8 people, but usually not too busy. I recommend bringing your own pillow and make iced coffee at night for the next morning because the keurig is noisy in the a.m.. The washing machine was such an asset. Always had hot water for showers and never for washing dishes. Am going to miss this place! Thank you so much Karine!
Condo rentals with a pool

Utopia Condo: Cozy, Quiet & Central with a Pool
We had a great stay in Anne Karine's apartment! Ideally located just on the edge of Marigot, perfectly quiet and a nice view over the lagune. The apartment is spacious, nicely decorated, has AC in both the living room and the bedroom and it has everything you need. The kitchen is perfect to make dinner, there are extra pooltowels, you can borrow a beach parasol and little chairs and dining outside is very cosy. We absolutely loved our stay and the communication with Anne Karine was excellent. Very higly recommended!

Beachfront property with pool view
Harry’s place was perfect for us, especially the private beach! Harry was extremely helpful, responsive and accommodating. Would def recommend his place 😊

Maho 1 Bed Condo with ocean view & Free Wi-Fi
From the very beginning Phil was very helpful and personable. Phil was very detailed on the instructions for check-in and the surrounding area. He provided recommendations for things to do and places to eat. He inquired if we had any questions or concerns, making us feel comfortable and at ease with renting from him. He already had pretty much covered 99.9% of the information that would have been needed, therefore we felt pretty much at home being in his place. We loved how well stocked the unit was re: towels, linen, kitchen supplies, the peacefulness of the unit and the cleanliness (which is definitely a plus plus for us) but above all the view from the unit was to die for. We enjoyed our time very much especially when lounging at the pool. We were especially grateful that he accommodated our check-out time. We will definitely be back. Thank you Phil for being a great host.

Sunset Lodge: sunny cozy, lagoon view & great deals
Carole’s place was great! The area is safe and very calm and cozy. The sunset views are awesome from either the patio or the pool. We felt right at home since the moment we arrived. Carole was super responsive, flexible for the check-in and helpful with instructions. The place is very clean and tidy with all required amenities. It’s great for a couple. You are close to Marigot (few mins) and driving distance 20-25 min to most places around the island. You will need a car to get around but you have a supermarket walking distance. We would definitely come back here if we come back! Overall, awesome experience!

Studio 113E Emerald
Spotless place … accommodating host for my early check in. Had a little trouble with lock box but realized it had 2 buttons on each side. I was pressing one.

Sbyc 3bdr with private jacuzzi and 3 shared pools
Beautiful condo with great views, and convenient to most places on the Island. Jolanda was very responsive to any questions and needs we had. Would definitely stay here again.

New Duplex Fidji
Terrific condo in the best location in Orient Village. Clean and comfortable and great hosts! We love the small well equipped kitchen for making breakfast and enjoying on the porch overlooking the gorgeous Orient Bay. It’s fun to watch the sailboats and yachts come in and out and the kite surfers from the living area, porch and front bedroom. Excellent host - proactive and responsive. Thank you for the memorable vacation!

LA VIDA - Duplex on the beach
It was a very tropical, beautiful view in the open air kitchen. The bathrooms and kitchen had very nice finishings. Very comfortable bed and furniture. Great air conditioning when needed. Great pool area with two pools. Nice breezes since you are right on the water. The condo grounds had beautiful palm trees and flowering plants everywhere. There's a great bakery and three restaurants on the water that are walkable from the unit. Mullet Bay beach was our favorite, a short distance away with three places for food. It's close to Maho Village also with a small shopping area with shops, restaurants and a casino. Romaine was a very responsive host if you had a question or need. A car is recommended. Beach chairs and a cooler were provided also.
Quick stats about condo rentals in Simpson Bay
Total rentals
100 properties
Nightly prices starting at
ﺩ.ﺇ257 before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
90 properties have a pool
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