
Condo holiday rentals in Simpson Bay
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Top-rated condo rentals in Simpson Bay
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Weekly condo rentals

Janel's Gem - Lovely 2- bdr condo in Weymouth Hill
My friend and I traveled together for a weekend to celebrate my birthday. The host was an amazing person, very kind, helpful and welcoming. The accommodation was well kept, the view was breathtaking both day and night time and we didn’t get any unsafe or uncomfortable feeling at all. In conclusion I recommend this Airbnb to anyone. It was definitely an amazing experience and one to remember 👍🏾👍🏾👍🏾

Studio COCO
Our Airbnb was exactly what we were expecting. It was cozy and quiet and had the perfect amount of space for the two of us. The outside patio was enclosed and provided an escape from the heat allowing us to enjoy eating meals and reading books while remaining outside. The pool was very clean and refreshing but could have benefited from some umbrellas for shade. The beach area was beautiful to look at but unfortunately the rocks prevented us from swimming. Our fave moment was the view we had outside our window of the beach, mountains and harbour in Marigot. The location provided walkable access to great restaurants along with a french bakery, rotisserie shop and a convenience store. The island has so much to see but arriving to our home base at the end of the day provided us with the tranquility we sought. Elisa was a wonderful host and answered our texts quickly. She had water, coffee and beer available for our arrival. We will return and couldn’t imagine staying anywhere else.

Vacation in Paradise on the Beach
We have always stayed at all inclusive resorts. We wanted to try something different but were hesitant about an Airbnb. Patrick's Villa was the first we viewed and nothing that we looked at online left the impression of La voyageur. Between the amazing reviews and beautiful decor, it just felt right. From our arrival, to departure and all the things in between, Patrick was an amazing host. From restaurant reservations to the best beach clubs, we were able to spend each second of our trip experiencing the best St. Martin had to offer. Patrick truly made our experience exceptional not to mention the unique atmosphere this flat provides. Beautiful views in a gated community with the best French cuisine within walking distance, we were truly in our perfect paradise. We purchased a few groceries and cooked a few times but ultimately felt at home. It was so very hard to leave. Thank you Patrick for offering a very special experience that we hope to revisit soon.

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!!

MAYA, Elegant Condo T2, Swimming Pool - Pinel
My husband, two year old daughter and I had the best time at Severine’s place. The home is beautiful and Séverine is an extremely responsive and communicative host. The outdoor terrace was used a ton. The pool is okay- we only used it once, we were mostly at the ocean. Who goes all that way to use the pool anyway?! Great quiet little neighborhood and close to orient bay. Amazing boulangerie up the street! The only thing I’ll mention is that to get into the apartment for the first time I had to message Séverine so she could let me in remotely, so I had to keep my phone on. I was hoping to avoid having my phone on data for the entire vacation. Not a big deal but something to note! Overall would highly recommend!

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!
My family and I enjoyed our spring break in Grand Case at Melinda and Ian’s place. Ian texted in advance of our arrival and met us promptly at the property to walk us through all the details, allow us to ask questions, and give us some proactive tips. It was such a kind gesture and made us feel welcome from the jump! The house is located beachfront, just steps from the water. We enjoyed the porch that was elevated enough to relax with a cocktail and watch our children play safely in the sand/sea. We were delighted to learn there was snorkel gear at the house for us to use, you can easily spot fish, starfish, etc. There are many restaurants located within short walking distance which we appreciated — ranging from local fare to high end dining. We felt beyond relaxed in the comfort of the property and are already discussing our return!
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!

Pet-Friendly Private Balcony Near Marinas & Beach
Great place to stay, wonderful roof terrace, awesome amenities, great location

Modern Oceanview Apartment
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

"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
Amazing host, would recommend!
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 Condo| Pool View + Private Beach Access
Very clean and very accessible area. About 15 minutes from the airport and very close to the port to visit Anguilla. There is a mini supermarket around. A mall walkable by 12 minutes, and bakeries too and a mini downtown area. The bnb itself is very clean, the neighbors are very polite as well. Harry is very helpful and super responsive. Would stay again. Good space for a couple, 2 friends, and great and safe for solo. I felt very safe. Thanks Harry

Studio "Between Land and Sea" 2
Sabrina was a super host. Very welcoming and available, impeccable apartment, private beach and beautiful pool corresponding to the description. Superb bedding, apartment prettier than in the photos. I will be sure to call on Sabrina the day I return to Saint Martin.

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.

New studio with superb view of the Caribbean Sea
Absolutely loved our stay here! From start to finish, everything was seamless. The host was incredibly friendly, welcoming, and full of helpful local recommendations that really enhanced our trip. The apartment itself was spotless, beautifully decorated, and had all the amenities you could possibly need for a comfortable stay — even better than the photos! The neighborhood felt very safe and was in a super walkable location, with tons of great restaurants, cafes, and shops just steps away. It was the perfect home base to explore the city. What really stood out was how thoughtful and attentive the host was. They truly go above and beyond to make sure guests feel at home — from the little personal touches to quick communication, you can tell they genuinely care. If you're considering booking, don't hesitate — this place is a gem. I’d 100% stay here again and recommend it to anyone looking for a cozy, clean, and convenient place with an amazing 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.

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
$110 AUD before taxes and fees
Total number of reviews
3.2K 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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