Vacation rentals with a pool in Simpson Bay Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Simpson Bay Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

A sunlit patio area features several lounge chairs positioned near a swimming pool. The modern architecture includes white walls with teal accents, while palm trees are visible in the background. Clear blue skies create a bright, inviting atmosphere.

Guesthouse in Cole Bay

4.93 out of 5 average rating, 29 reviews

New ! Apartment with pool and ocean view #1

Newly renovated apartment with swimming pool and ocean view. Ideally located in Pelican Key, next to the beach, restaurants, groceries, bars, casinos, clubs, next to Simpson Bay and close to the airport. This apartment, "Aruba", is part of Ruby Blue Residence with 5 other independent apartments, swimming pool, garden, laundry with washer and dryer, private free parking. Adult only ! Enjoy your vacation in our peaceful place ! Sint Maarten is currently experiencing some daily power outages

Guest favorite

A living area features a modern television mounted on a minimalist white console. A circular coffee table sits below, accompanied by a decorative shell. Light filters through sheer curtains, illuminating the space and offering a glimpse of the outdoor area.

Condo in Marigot

4.93 out of 5 average rating, 41 reviews

Beachfront Condo| Pool View + Private Beach Access

Welcome to Perle des Sables, nestled in Marigot, this exquisite vacation rental lives up to its name, offering an idyllic escape on a private beach. Immerse yourself in the tranquil embrace of turquoise waves, sink your toes into the soft white sand and witness breathtaking golden sunsets painting the skies of St. Martin. With its prime location in a secured private residence, it ensures both serenity and peace of mind. Experience the epitome of beachfront paradise in this extraordinary haven.

Superhost

An outdoor terrace is visible, featuring a small table and two chairs. Beyond, a serene view of palm trees and water is seen, complemented by the soft reflection of the sky on the surface. The space is surrounded by light, airy fabric drapery.

Apartment in Collectivity of Saint Martin

5 out of 5 average rating, 6 reviews

Just in paradise with lagoon's view

Situé au 2ème étage, avec une superbe vue , dans une charmante résidence à la Baie Nettlé. Joliment décoré, tout confort, entièrement équipée et climatisé. D'une surface de 50m2, idéal pour une ou deux personnes (deux à deux places) , cet appartement peut accueilr jusqu'à 9 personnes (lit bébé et lits singles supplémentaires fournis sur demande) Coin salon Espace bureau salle à manger sur la terrasse et canapé-lit single Salle de bain avec baignoire 2 piscines Coucher de soleil inoubliable !

Guest favorite

A cozy sleeping area features a spacious bed adorned with a checkered white and black blanket. Decorative towels are arranged in a heart shape, complemented by fresh flowers. A warm light is emitted from a stylish lamp beside the bed, with a palm tree artwork above.

Apartment in mont Vernon 2

4.89 out of 5 average rating, 9 reviews

the cozy corner studio in Mont Vernon 2

You'll have a great time at this comfortable place to stay. affordable and friendly location . you are 5 minutes from grand case by car, 8 minutes from orient bay and 2 minutes from hope estate. there is a small pool area that is shared between guests as well as a lounge area in the yard where we find guests chatting and sharing experiences of the island we also have a small car rental company send a message for more info.🌴 airport / port pick up available when renting a car.

Superhost

A private pool is framed by a circular terrace, surrounded by lush greenery and palm trees. A gazebo with a thatched roof offers shade, while the ocean view extends beyond the horizon, highlighted by a clear blue sky with scattered clouds.

Villa in Cole Bay

4.69 out of 5 average rating, 29 reviews

Pelican key Home with the view

This villa provides a great escape for a family vacation, honeymoon or anniversary. Treat yourself with this beautiful villa and an unforgettable ocean view. A gated luxury 3bedroom, 2 bath with a private pool. Enjoy your romantic evenings around the outside dining table or cook a family dinner in the well equipped kitchen. Even though in a very secluded location it is convenient to all amenities including shopping, restaurants, supermarkets, beaches, casinos and night life.

Guest favorite

Two inviting swimming pools are set within a serene complex, surrounded by vibrant buildings in various colors. Palm trees provide a tropical touch, and the clear blue sky enhances the tranquil environment.

Condo in Collectivity of Saint Martin

4.98 out of 5 average rating, 59 reviews

Feet in the ocean, Orient Bay, Beach apartment

Si vous rêvez de mer turquoise et de sable blanc cet appartement est fait pour vous. Grace à son accès direct à l’immense plage de la Baie Orientale et les deux piscines de la résidence, c'est l'endroit idéal pour des vacances les pieds dans l'eau. Idéalement situé en première ligne face à la mer, dans le domaine sécurisé d'Orient Bay. Venez profiter de ce spacieux T2 tout confort à la décoration soignée, dans une résidence calme, verdoyante et proche de toutes commodités.

Superhost

A private pool area features clear blue water surrounded by light-colored tiles. Two white lounge chairs are positioned beside the pool, and a small table is located nearby. The space is bordered by a yellow exterior wall and includes glass doors leading indoors.

Apartment in Oyster Pond

4.87 out of 5 average rating, 125 reviews

Lovely Studio Apartment with Pool & Nature Views!

Take a break and unwind at this peaceful studio apartment, perfect for your Caribbean getaway! This fully equipped studio is located just 7-10 minutes away from the capital, Philipsburg, and a few minutes away from several beautiful beaches. It also has gorgeous scenic views and an inviting and relaxing pool! As well as a rooftop terrace with scenic 360 views. Baby crib and grill available upon request for small fee and washer & dryer available on premise for free use.

Superhost

A private pool extends seamlessly into the view of the beach and ocean. Comfortable seating is arranged on the terrace, complemented by a vibrant green plant. The distant mountains and fluffy clouds form a picturesque backdrop against the bright blue sky.

Condo in Pelican

4.66 out of 5 average rating, 64 reviews

SeaLaVie Apartment with Private Pool

Welcome to the stunning St. Maarten Beachfront Apartment with Private Pool! This luxurious Airbnb property offers an unforgettable vacation experience in one of the most beautiful and sought-after destinations in the Caribbean. Perched on the pristine white sands of St. Maarten's exquisite Kimsha beach, this beachfront apartment boasts breathtaking panoramic views of the turquoise waters and the endless horizon.

Superhost

The outdoor area features a private pool surrounded by tiled patio flooring. Two lounge chairs are positioned nearby, and a large window with yellow shutters offers an inviting entrance to the villa. Lush greenery complements the tranquil setting against a bright blue sky.

Villa in St Martin

5 out of 5 average rating, 11 reviews

Villa Jeluca with pool - sxm island vacation

Located on the heights of the eastern bay, a recent villa, 3 bedrooms and swimming pool, in the immediate vicinity of the most beautiful places of the French part. From the huge terrace you have a breathtaking view of the eastern bay and its ocean. A few minutes from the beach of the eastern bay and the village square. Enjoy with your family this fabulous accommodation that offers good moments in perspective.

Superhost

A spacious private pool is bordered by a sun terrace featuring several lounge chairs. The modern architecture of the villa is visible in the background, with expansive glass doors providing a view of surrounding hills and the coastline.

Villa in Lowlands

4.88 out of 5 average rating, 16 reviews

Reflection Y 5 Star Villa

Our modern style will surely have you feeling like you are living in the lap of luxury. One-of-a-kind panoramic view in this 5-Star Villa! Conveniently located nearby the beautiful Mullet Bay Beach, Casinos, restaurants, shopping in the Maho Village, and the world-famous plane landing experience at the airport. Car Rental deals available upon request and an all-around vacation package!

Superhost

A clear view of the pool area is presented, featuring lounge chairs arranged around a swimming pool. Umbrellas provide shade for seating areas. The landscape includes lush greenery and distant views of buildings against a bright blue sky, enhancing the sense of space and relaxation.

Apartment in Lowlands

4.84 out of 5 average rating, 73 reviews

Modern Studio in gated Resort pool & gym.generator

This Resort-like living Studio is close to the island main attractions, Mullet Beach, Maho night life area, Casino Royale, shops, supermarket. 5 minutes drive from international airport. Walk to the beach, restaurants and nightlife. Sports club next door, padel, soccer, pickleball. Pool, bbq, gym, bakery, fitness center, sand volleyball on property.

Guest favorite

The image captures a private infinity pool surrounded by lush greenery and palm trees. The calming blue water reflects the sky, while a scenic view of the coastline and distant ocean is visible in the background. Lounge chairs are positioned nearby for relaxation.

Guesthouse in Little Bay

4.86 out of 5 average rating, 228 reviews

Your oasis with spectacular views and private pool

Long idelness by the infinity pool. Two bedrooms each with its own bathroom and seperate toilette. A few minutes from the beach, shops and nightlife and yet in a quiet and safe area. The guests has the entire home with a private pool. Please check “villa_pi” on instagram for more photos

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What guests are saying

Ocean View Villa-Indigo Bay W/Private Pool/0 Steps

5 out of 5 average rating, 26 reviews4 days ago

Firstly This place is paradise. Second This is the cleanest Airbnb I have ever booked! Seriously clean as a whistle. The decor was perfect without being over done. The panoramic view from the living room provided the perfect back drop to a cup of coffee and for dinner at night. We spent so much time in the pool Perfect size for our group. The host greeted up and kept in contact through our stay. The place was easy to find and navigate as well. Every room was spacious and allowed us to decompress at the end of the day! I can’t wait to come back!

Home in Sint Maarten

What guests are saying

Villa vue mer, piscine et jacuzzi

4.95 out of 5 average rating, 20 reviews1 month ago

Francois was a great responsive host. He guided us to the house and showed us around. The place was squeaky clean and just as the pictures showed. The road was a bit winding and steep to get there but we adjusted and became more comfortable as the week went on. If you’re an older couple, this may not be the place for you as the driveway is steep and you need to drop the trash at the end. The winding stairs inside also might not be ideal for the elderly. Anse Marcel beach is a gem and I love that our place was away from the tourists. It’s super close to the Pinel Ferry and grocery store. Thanks for a great visit!

Villa in Anse Marcel

What guests are saying

Luxury, Villa Panoramic Sea Views, Pelican Key

4.86 out of 5 average rating, 29 reviews11 months ago

We had an amazing time staying in Mike's home. The house itself is clean, safe, and a perfect place to relax in the pool with a view. Michael was a great communicator leading up to the trip and gave us fantastic recommendations. Once we arrived, Peaches was there for us in everyway, constantly responsive to our questions and even picked up a lost item from a taxi for us! My biggest recommendation if you stay here is to rent a car, the house is a bit further back in a neighborhood ( makes for a nice and quiet area) but pretty difficult if you would like to walk anywhere. There are restaurants and bars just a few minutes away a long with a number of grocery stores. Driving to both Marigot and Phillipsburg only took around 15-20 minutes depending on traffic, so the house was in a great location to get around the island. Would absolutely stay there again.

Home in Cole Bay

What guests are saying

Gorgeous Oceanview Apartment W/Generator

5 out of 5 average rating, 4 reviews3 months ago

Saul’s place is fantastic with a pool just outside surrounded by picturesque bougainvillea trees. Located toward the top of Pelican Hill, the apartment has a view of the ocean that is absolutely spectacular…like sleeping in the eagle’s nest of the island. The unit is comfortable and quiet; however, its close proximity (3 minute drive or 10 minute walk) to the hustle and bustle of Simpson Bay gives the feeling of being in the center of all the action. As not many areas of the island are walkable, the entire Pelican neighborhood is a wonderful option for its clearly indicated sidewalks and consistently low traffic patterns compared to the rest of Simpson Bay where there are boutiques and grocery stores galore, an endless array of restaurants featuring almost any cuisine you can imagine, nightclubs, bars, and quite a bit of traffic. The unit, itself, was very clean with a large living space that is rare for the island. Saul is a phenomenal host. We can’t wait to come back soon!

Apartment in Cole Bay

What guests are saying

Exquisite 2 Bed Luxury Apt w Views Walk to Beach

5 out of 5 average rating, 5 reviews1 week ago

Fourteen is an absolutely gorgeous property. My son is a student at the medical university nearby and the location was perfect for us ! The view is incredible. Mullet Bay beach is the best beach on the island, pool was great too! Beds were super comfy ! Would stay here again! Jeff was super friendly and had great suggestions. Thank You!!

Apartment in Cupecoy Beach

What guests are saying

Family friendly 2 bedroom home with private pool

5 out of 5 average rating, 4 reviews13 months ago

Manoj en Mariana hebben er alles aan gedaan om ons verblijf zo fijn mogelijk te laten zijn. De woning is smaakvol ingericht en heeft een heerlijk zwembad en terras. Opvallend was ook de vriendelijkheid in alle contactmomenten. Manoj heeft gastvrijheid en service hoog in het vaandel staan. Het verblijf in de woning heeft bijgedragen tot een geweldige week op Sint Maarten

Home in Little Bay

What guests are saying

Tropical Getaway Sxm!

5 out of 5 average rating, 3 reviews1 month 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.

Apartment in DUTCH CUL DE SAC

What guests are saying

5B Oceanview villa near Philipsburg

5 out of 5 average rating, 8 reviews1 month ago

Jennifer is an amazing host. She responds quickly and is very courteous; going out of her way to make sure our stay was exceptional. The house is well kept and clean. It was also so nice and convenient to have laundry in house! Our family made great use out of the pool, which was cleaned regularly during our stay. We would definitely recommend this place!!

Home in Little Bay

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