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Holiday rentals with a pool in Simpson Bay Beach

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Popular amenities for Simpson Bay Beach rentals with a pool

House rentals with a pool

Top guest favourite
Home in Koolbaai
5 out of 5 average rating, 14 reviews

New-Sunset Place Villa w Stunning Waterfront Views

ElisabethRating, 5 stars1 week ago
We had such a wonderful time and can’t wait to return! This is a perfect place for a family or small group of friends. The location is wonderful—in a quiet area, but not far from restaurants, groceries, etc.—and the views are amazing!! We spent a lot of time on the deck—sunning, eating, taking dips in the pool, watching boats pass by, and enjoying incredible sunsets! From beginning to end, Joy and Sandrine were so responsive and very patient in answering all of our questions. Joy sent information ahead of our stay about excursions and restaurants, and she was available to make bookings when needed. We highly recommend this property and would definitely stay here again!
Guest favourite
Home in Caribbean
4.89 out of 5 average rating, 53 reviews

Pelican Paradise

PhilippeRating, 5 stars3 weeks ago
Perfect little villa (actually much bigger than we expected), located in the best neighbourhood of St-Maarten, and managed by a true Superhost!
Superhost
Home
4.85 out of 5 average rating, 20 reviews

Villa Louisiana

TeresaRating, 5 stars1 week ago
This place was amazing. It was exactly as it was described. We had anywhere from 2-8 of us at a time and there was plenty of space and bathrooms also worked out great. We would go back here again.
Superhost
Home in Mont vernon 3
4.67 out of 5 average rating, 3 reviews

Villa Carib sxm piscine.

AshantiRating, 5 stars9 months ago
First, the pictures really don’t do this place justice. Second, Flo was beyond amazing, I would definitely recommend this place to anyone who’s traveling to St.Maarten! Till next time Flo! <3
Top guest favourite
Home
5 out of 5 average rating, 41 reviews

Water access, snorkeling gear & kayaks

MonicaRating, 5 stars2 weeks 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!
Superhost
Home
4.8 out of 5 average rating, 10 reviews

Maison les Sucriers, Baie Orientale le Village

ChristineRating, 5 stars3 months ago
We had a very nice stay. The location of the house is fantastic and is close to all restaurants, beach grocery store. The host was very flexible when we arrived and we are very grateful for that . The place was very clean and well maintained. We'll definitely be back! Thank you!
Guest favourite
Home in Cole Bay
4.98 out of 5 average rating, 43 reviews

Modern 3BR with Private Pool

JeremyRating, 5 stars1 month ago
Cannot say enough positive things about Sabrina. She was a fantastic host and the place is exactly as pictured- spacious, clean, and great decor. Any questions we had were responded to very quickly. She also helped us out even after check-out when our flight was cancelled. Great location and central for exploring the island and its beautiful beaches. Thank you for everything Sabrina!!!
Superhost
Home in Cole Bay
4.78 out of 5 average rating, 9 reviews

Sunset Views Designer 3 Bedroom House

MatthewRating, 5 stars2 weeks ago
Great spacious and clean home, fully equipped with everything you need for young kids as well. Large master suite with very comfortable beds. Dan sends very clear and detailed instructions that are very helpful for thr stay. I hope to be back soon. Thanks for having my family!

Apartment rentals with a pool

Superhost
Apartment in Lowlands
4.76 out of 5 average rating, 79 reviews

Loft Condo - STEPS FROM BEACH!

DonRating, 5 stars1 week ago
Jaynes place was great and well worth what we paid for it. She is a great host and helped with booking attractions and tips on great local spots. We will look forward to booking with her again in the future. The island always passes any expectations you would have for a great vacation and Jayne just helps to make it that much more pleasant.
Top guest favourite
Apartment in Simpson Bay
5 out of 5 average rating, 35 reviews

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub

HowardRating, 5 stars2 weeks ago
This was a very safe and secure unit in the heart of Simpson Bay. The unit was perfect for our stay, nicely furnished, had fantastic outdoor space and was quite comfortable. The hosts Mariana and Manoj are great communicators who made us feel very cared for while at the property! Thank you both so much for a great stay!!
Top guest favourite
Apartment in Lowlands
5 out of 5 average rating, 38 reviews

The Cliff in Cupecoy Beach HEAVEN!!!

BruceRating, 5 stars1 month ago
The communication with Joe and the stay was excellent. The amenities were great and whoever he has doing the housekeeping, does a great job. The concierge at the front desk is like being at a hotel and there’s a restaurant right on site like staying at a four star hotel with having your complete privacy to yourself
Top guest favourite
Apartment
4.98 out of 5 average rating, 51 reviews

Utopia Condo: Cozy, Quiet & Central with a Pool

DaphneRating, 5 stars2 months ago
We stayed in Anne's apartment for a few days between our holiday in Orient Bay and flying out home, we wanted somewhere conveniently close to Marigot, shops and restaurants and Anne's place was just what we wanted. The place was clean, equipped with all modern amenities and the sunsets were beautiful. Anne was super proactive in her communication.
Top guest favourite
Apartment in Lowlands
4.88 out of 5 average rating, 40 reviews

Maho 1 Bed Condo with ocean view & Free Wi-Fi

FlorRating, 5 stars2 months ago
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.
Superhost
Apartment in Upper Prince's Quarter
4.83 out of 5 average rating, 6 reviews

Beautiful, airy 2BR condo overlooking Dawn Beach

StevenRating, 5 stars14 months ago
All around a great place to stay, one needs a car to get around to beaches and food stores. The views from our balcony was beautiful would recommend.
Top guest favourite
Apartment in Simpson Bay
4.98 out of 5 average rating, 62 reviews

The Beach Condo

TonyRating, 5 stars1 month ago
We have been coming to SXM for 15 years and I have stayed all over the island and this is my favorite. The beach, the pool, at your doorstep, it is beautiful! You can't ask for anymore. I have already rebooked for next year!
Guest favourite
Apartment in Little Bay
4.95 out of 5 average rating, 19 reviews

Little Bay- Caribbean Blue View, 2 bed, sleeps 6

SammyRating, 5 stars2 months ago
Lovely location! Really enjoyed our stay here and would definitely come back. Felt very homey and comfortable, it was perfect. The view was amazing and made the hill up 100% worth it. You really get used to the drive after the first time. There's an amazing beach called Great Bay Beach right near by and a great on the beach restaurant called Eat Something. Ask for Lenny if you want to eat and rent chairs there, he's the best!

Home rentals with a private pool

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