Vacation rentals with a pool in Simpson Bay Beach

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Top-rated rentals with a pool in Simpson Bay Beach

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Guest favorite

A clear swimming pool reflects sunlight, featuring tranquil ripples across its surface. In the background, several blue lounge chairs are arranged on a deck, flanked by lush greenery, providing a serene environment for relaxation.

Condo in Simpson Bay

4.97 out of 5 average rating, 91 reviews

Beach front luxury! Huge 2BR that has it all! 😍🤩😍

5 star hotel luxury is yours in this modern beach home! 2 guest rooms with en-suite bathrooms and deck access. Enjoy cooking your own meals and dine inside or on the deck (or beach!). Largest deck on Simpson Bay beach has it all: huge daybed, loungers, living and dining areas for your comfort and pleasure. Unwind in the den and enjoy the big screen there or in either bedroom. Your neighbor is a boutique hotel and will gladly serve you meals and drinks right to your deck! Much more info available

Guest favorite

A rooftop pool area is presented, featuring an infinity edge that overlooks the ocean. Comfortable lounge chairs are arranged along the pool deck, with clear blue skies and distant hills visible in the background. The tranquil water reflects the sunlight, creating a serene ambiance.

Home in Simpson Bay

4.92 out of 5 average rating, 12 reviews

Townhouse Villa LX

Superbe Maison mitoyenne, faisant partie d’une petite copropriété sécurisée dans le quartier de Beacon Hill. Située à 5 minutes de l’aéroport, vous pourrez admirer le ballet unique des avions au dessus de la plage de Maho, sans nuisances sonores, depuis la piscine commune installée sur un rooftop. Très spacieuse avec ses 3 belles chambres, 2 salles de bain, entièrement climatisée, terrasse arborée et cuisine équipée. Située à proximité des restaurants et clubs. Accès plage direct en 1 minute.

Top guest favorite

A spacious swimming pool is framed by lush landscaping and poolside chairs, offering a serene view of the ocean. The clear blue water reflects the sky, with a backdrop of gently swaying palm trees and distant ships on the horizon.

Condo in Simpson Bay

4.99 out of 5 average rating, 68 reviews

The Beach Condo

The Beach Condo, located in Palm Beach Apt. complex is a completely newly renovated 2 bedroom condo right on Simpson Bay Beach. Equipped with all amenities, this is your ideal tropical luxurious getaway. A brand new, fully equipped kitchen, large living and dining area and two king size bed-bedrooms with individual bathrooms give you all the space you need for a retreat in the Caribbean. Lounge on the porch, swim in the pool or live it up on the beach, it's all right there for you to enjoy.

Superhost

An infinity pool extends over the edge, offering panoramic views of the lagoon. The tranquil water reflects the blue sky, while steps lead from the pool's edge to the terrace. Lush greenery is visible, enhancing the serene atmosphere of the space.

Guest suite in Cupecoy

4.9 out of 5 average rating, 110 reviews

Panoramic View Terrace Infinity Pool Top Penthouse

Wake up to the magnificent panoramic view of the lagoon on the top floor, rejuvenate your body with a refreshing dip in the private rooftop infinity pool with a coffee or tropical drink. Take a 10 mins stroll to the famous Mullet bay Beach and grab a few freshly French croissants by the Square. After sunset, enjoy the plentiful neighborhood bars and restaurants or take 5 mins drive to Maho where you will find a vast variety of restaurants, casino and clubs or Porto Cupecoy for romance spot.

Top guest favorite

A spacious swimming pool is surrounded by lush greenery and palm trees. Lounge chairs are positioned around the pool area, which reflects the clear blue sky and is adjacent to a series of two-story white buildings with blue roofs.

Condo in Simpson Bay

5 out of 5 average rating, 29 reviews

Beachfront Caribbean Breeze in Paradise, SXM

Caribbean Breeze inviting Beach front home. A few steps to our beach and pool. Walk to mainstream. Amazing views . 2/2.5 with huge Master. Hear the waves flowing in onto the shore for those relaxing days and nights. New kitchen, living room , bathrooms, dining area,etc. Unwind on any balcony, penthouse ocean view, on daybed with a nice drink , looking over the verse tranquil ocean. Take a dip in the soothing crystal clear waters, 1 minute walk away. Amenities enclosed & Wi-Fi included.

Top guest favorite

A private pool is surrounded by a wooden deck, featuring multiple lounge chairs arranged for relaxation. The space offers a clear view of the sea and distant hills, complemented by a bright sky with scattered clouds. The outdoor area invites enjoyment of the coastal scenery.

Loft in Marigot

4.99 out of 5 average rating, 161 reviews

Sea Loft Vue imprenable - piscine privée

* Loft de 200m² * Vue mer exceptionnelle * Piscine privée * A 250 mètres de la petite plage de Galisbay * Terrasse avec chaises longues, salon de jardin, table d'extérieur et BBQ * Espace bureau * Wifi 100 Mbps * TV avec milliers de chaines du monde entier * A 250 m à pied de la marina Fort Louis de Marigot * A 5 min à pied du centre ville de Marigot avec ses restaurants, boutiques et autres commerces * A 5 min de l'embarcadère pour Saint-Barth et Anguilla, et de la station de taxis

Guest favorite

Condo in Maho

4.9 out of 5 average rating, 210 reviews

Serene Oasis: Unwind by the Rooftop Pool & Hot Tub

This charming, cozy, and tranquil tropical nest is located where all the action is! The golf course, iconic bars, the unprecedented landing strip, the popular Maho and Mullet bay beaches, Maho market with daily fresh take away breakfast/lunch buffets and a divine selection of exotic restaurants are all in walking distance! If you wish to just lounge and relax by the pool, jacuzzi, and private gazebo bar or enjoy the nightlife; it’s all readily available, at your fingertips!

Superhost

A spacious outdoor seating area features comfortable wicker furniture, including a circular sofa and lounge chair. Lush tropical plants and vibrant flowers provide a scenic backdrop, while distant green hills are visible under a partly cloudy sky. A glass coffee table sits centrally among the seating.

Home in Calabash Rd, Cole Bay

4.89 out of 5 average rating, 149 reviews

THE HILL HOUSE, 2 Bdr, pool, panoramique vue

Hébergement avec piscine privée et vue à couper le souffle Offrez-vous une parenthèse de rêve dans cette maison élégante, nichée dans le quartier sécurisé Almond Grove Estate. Profitez de 2 chambres climatisées, d’un salon lumineux, d’une cuisine équipée, et surtout d’un espace extérieur idyllique avec piscine et vue panoramique sur Simpson Bay. À seulement 5 min de Marigot, 10 min de l’aéroport et 15 min des plages, c’est l’adresse parfaite pour un séjour inoubliable !

Superhost

The image depicts a clear blue swimming pool surrounded by lounge chairs and tropical palm trees. In the background, the ocean can be seen alongside a beach area with a white railing, under a bright sky featuring fluffy clouds.

Apartment in Simpson Bay

5 out of 5 average rating, 4 reviews

1-bdr condo in Beachfront Residence, Simpson Bay

This amazing completely renovated 1 bedroom 1.5 bathroom unit is located at Palm Beach Condo’s, directly on Simpson Bay Beach. Palm beach is very convenient located in Simpson Bay, here you will find beach bars, restaurants and supermarkets within walking distance. Only a 10 minute drive from the airport. Palm beach offers you a large common pool and private access to the beach. Enjoy your day on the beach, at the pool or go on an adventure on our beautiful island!

Superhost

A private pool is framed by a wooden deck, offering lagoon views. Two lounge chairs are positioned nearby, with a small round table beside them. The surrounding area is brightened by natural sunlight, enhancing the serene waterscape.

Apartment in Point Pirouette

4.91 out of 5 average rating, 118 reviews

Secret View amazing apartment- Private pool

Welcome to Secret View, a stunning, fully renovated, stylish and modern apartment located directly on the lagoon with a private pool and breathtaking views. Quiet and secure area, next by Maho, Mullet Bay, the golf course, supermarket, bars, restaurants, and casinos. A true sanctuary, it’s sure to be the highlight of your holiday. Private and free parking Your ultimate vacation retreat. Sint Maarten is currently experiencing some daily power outages

Guest favorite

A serene outdoor space features two lounge chairs adorned with towels, facing a small plunge pool. The area overlooks the stunning Caribbean Sea, enhancing the calm ambiance with lush greenery in the background and a clear blue sky.

Apartment in Indigo bay

4.95 out of 5 average rating, 103 reviews

Appartement indépendant bas de villa - Indigo Bay

L'appartement de la Villa Stella vous accueille dans un cadre unique avec une vue spectaculaire sur la mer des Caraïbes. Située dans une résidence sécurisée 24h/24, la tranquillité est au rendez-vous. Vous serez à seulement 8 min à pied de la plage d'Indigo Bay et proche des commerces et restaurants de la partie néerlandaise. Composée de 2 chambres et de 2 salles de bain, vous pourrez vous détendre dans la piscine/jacuzzi surplombant la baie .

Guest favorite

A panoramic ocean view is captured from the terrace featuring a private heated pool. The crystal-clear water of the pool reflects sunlight, while the vast sea and distant islands are visible under a bright blue sky with scattered clouds.

Apartment in Little Bay

4.94 out of 5 average rating, 125 reviews

Stunning Ocean View - 2 / 3 Brm Terraces Lt. Bay

Treat yourself to the stylish and modern ocean view apartment . This spacious environment, is designed to be enjoyed as a family, has a terrace with stunning sea view, climatized private pool, two master suites (one w/Japanes king bed and walking closet), the other with two double size beds (you can join them and make a king bed) and closet and a third room with daybed. All of them with their own bathroom and ocean view. Welcome!