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Holiday rentals with a pool in Simpson Bay

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Simpson Bay

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

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Guest favourite
An outdoor terrace features a wooden deck, complemented by various potted plants. A glass table is surrounded by light-colored chairs. In the background, a sparkling blue pool is visible, alongside a lush green area and a view of the coastline and sky.
Home
5 out of 5 average rating, 15 reviews

Modern Bungalow with Stunning Seaview & Pool

Découvrez notre Luxueux & Cosy Bungalow Kombawa, chambre séparée, cuisine tout équipée, canapé lit à disposition dans le salon, grand placard, douche à l'italienne, idéal à 2 ou 3, ou en famille. Il est situé à quelques minutes à pied de la très belle plage de Baie aux Prunes, la vue époustouflante vous permettra d'admirer les couchers de soleil sur la mer. Venez vous ressourcer au coeur de cet écrin de verdure à la douce mélodie du chant des oiseaux idéalement situé entre les 2 parties de l'île

Top guest favourite
The private patio features a saltwater pool with ocean views, complemented by lounge chairs and tropical plants. Soft clouds drift overhead, enhancing the serene atmosphere. Nearby, a dining area offers an inviting space for meals while overlooking the lush garden and the expansive sea.
Home in Cole Bay
4.82 out of 5 average rating, 22 reviews

Luxury Villa Turquoise Heaven in Pelican Key

Welcome to Villa Turquoise Heaven- Modern Luxury in Pelican Key, SXM Experience the pinnacle of Caribbean elegance at Villa Turquoise Heaven, the newest luxury villa in the exclusive Tepui Residence. Designed for relaxation and style, this modern retreat offers a seamless blend of indoor-outdoor living with unparalleled views of the turquoise Caribbean Sea. From waking up to the gentle sound of waves to savoring sunsets from your private infinity pool, Villa TH offers an unforgettable escape.

Guest favourite
A cozy living area features a comfortable gray sofa and a wooden coffee table. Two windows offer expansive views of the ocean, with light reflecting off the water. Beams stretch across the ceiling, enhancing the airy feel of the space.
Apartment in Simpson Bay
4.8 out of 5 average rating, 183 reviews

Oceanfront w Pool | Maho Beach area

Location , Location Location ! You can not get any closer to the ocean than in this cliff side apartment. The sound of waves crashing below and incredible ocean views from every room. The sunrise is magical everyday and by night the glowing lights of Simpson bay. This cliff side apartment has everything you need for a dream stay away from the crowds. . Just steps from 4 beaches Simpson bay, Mullet bay, burgeux bay and a 5minute walk to the world famous Maho Beach with its famous plane landings

Superhost
Home in Simpson Bay
4.67 out of 5 average rating, 3 reviews

Coco's Beach House - Simpson Bay Beach

Coco's Beach House is a stunning property just steps away from the Simpson bay beach. It will leave you feeling like you are in paradise, 2 King bedrooms with ensuite, full kitchen, 2 private patios, glittering glimpses of the beautiful turquoise ocean and all the comforts of home. It is the perfect spot for 2 couples or a family with small children. Situated in the heart of the Island, we are walking distance to some of the nicest restaurants on the island, bakery, restaurants & nightlife.

Top guest favourite
Flat in Upper Prince's Quarter
5 out of 5 average rating, 17 reviews

Aman_Aria

This unique place has a style all its own, newly built, contemporary retreat features two elegant master bedrooms, each with its own private bathroom, a spacious living area seamlessly connected to a fully equipped kitchen, an inviting outdoor terrace. Every bedroom and the living room offer uninterrupted vistas of the mesmerizing ocean. The heart of Aman is its spectacular infinity pool and sun-drenched deck, inviting you to relax while soaking in breathtaking panoramas.

Guest favourite
An aerial view of the villa showcases its modern architecture with a terracotta-tiled roof and expansive outdoor spaces. A large infinity pool reflects the surroundings, while shaded areas with loungers and a fire pit area provide spaces for relaxation and gathering.
Villa in Upper Prince's Quarter
4.95 out of 5 average rating, 115 reviews

The Blue Door Villa - 4 bed ocean view home

At the Blue Door Villa, we offer our guests all the creature comforts of being in a well-equipped vacation home. We are located on the Dutch side, minutes from the French border in a quiet gated community. The Blue Door Villa is a perfect place to relax while you listen to ocean waves and swim in the infinity pool. There are multiple outdoor spaces offering privacy or space to gather. We are now offering our guests an exclusive, free concierge service.

Top guest favourite
An outdoor terrace features comfortable white lounge furniture arranged around a coffee table. Sun loungers are positioned beside a private infinity pool, overlooking the ocean and distant boats. The scene is framed by tropical plants and a clear blue sky, enhancing the serene coastal environment.
Loft
4.99 out of 5 average rating, 184 reviews

Sea Loft, Breathtaking View – Private Pool

* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with lounge chairs, garden furniture, outdoor table and BBQ * Office area * 100 Mbps Wi-Fi * TV with thousands of channels from around the world * 250 m walk to Fort Louis de Marigot Marina * 5 min walk to Marigot city center with its restaurants, boutiques and other shops * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

Guest favourite
A serene infinity pool extends to the horizon, bordered by smooth stone tiles. Three light blue loungers are positioned for relaxation, overlooking the expansive sea and a clear blue sky scattered with clouds.
Villa in Beacon Hill
5 out of 5 average rating, 22 reviews

Infinity Ocean Edge - Luxury Oceanfront Penthouse

✨ Infinity at Ocean Edge with IRE Vacations✨ 15% Discount on select dates* Come take advantage of this luxury property located on the end of the Beacon Hill peninsula, ensconced on all sides by the inviting Caribbean Sea! This spectacular waterfront property is one of a kind. Located just minutes from several of St. Maarten’s most popular beaches and beach bar hangouts, a great day is always guaranteed. This property is not kid friendly.

Guest favourite
An outdoor terrace features a private pool and a dining area with a table and chairs. Sun loungers are positioned nearby, surrounded by tropical greenery. A scenic view of the water and distant buildings can be seen, with sunlight illuminating the wooden deck.
Flat in Lowlands
4.96 out of 5 average rating, 24 reviews

The Lost Paradise

Ce magnifique appartement, situé près des plages de Maho et Mullet bay et du quartier touristique de Maho, est idéal pour passer de superbes vacances. Très fonctionnel, il est parfait pour 4 personnes avec ses 2 salles de bains et sa chambre indépendante. Un lit escamotable dans le salon servira de second lit. Situé sur la presqu’île pittoresque de Point Pirouette, ce logement unique vous fera passez de merveilleux moments.

Top guest favourite
A private heated pool is featured at the edge of the terrace, offering views of the ocean and nearby islands. The clear blue water contrasts with the light-colored stone surrounding the pool, while lush greenery can be seen in the background against a clear sky.
Flat in Little Bay
4.99 out of 5 average rating, 169 reviews

Stunning 2 BD Ocean View - Terraces Lt Bay

Treat yourself to the utmost stylish and modern ocean view apartment located in the exclusive Little Bay Hill . This spacious environment, is designed to be enjoyed as a family, has a terrace with stunning sea views, private pool, one master suites ( Japanese king bed and a walking closet), one bedroom suite with two twin size beds ( could be converted to king size bed ) . Welcome to Terraces Little Bay !

Guest favourite
A modern living area is presented, featuring a gray sofa with decorative pillows, positioned on a light-colored rug. Large glass doors provide access to a balcony with views of the surrounding landscape. Natural light fills the space, highlighting the minimalist décor and coastal ambiance.
Flat in Cupecoy Beach
5 out of 5 average rating, 18 reviews

B-804 Splendid 1 bedroom Ocean corner view

Welcome to Fourteen at Mullet Bay, the most exquisite and luxurious beachfront residence in St Maarten located directly on the famous Mullet Bay beach and golf course.<br><br>As you enter this beautiful one bedroom condo apartment on the 8th floor, you will directly feel at ease overlooking the stunning white sandy beach of Mullet Bay and its breathtaking turquoise waters.

Top guest favourite
An inviting outdoor space features a private pool surrounded by lush greenery and sea views. Comfortable lounge chairs are positioned nearby, providing a serene spot to relax. Sunlight reflects off the water's surface, creating a tranquil atmosphere.
Flat in Indigo bay
4.94 out of 5 average rating, 122 reviews

Independent apartment at the bottom of the villa – Indigo Bay

The Villa Stella apartment welcomes you in a unique setting with spectacular views of the Caribbean Sea. Located in a 24-hour secure residence, tranquility awaits. You will be just an 8-minute walk to Indigo Bay Beach and close to shops and restaurants in the Dutch side. Composed of 2 bedrooms and 2 bathrooms, you can relax in the pool/jacuzzi overlooking the bay.

Popular amenities for Simpson Bay rentals with a pool

When is the best time to visit Simpson Bay?

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Avg. price£189£203£203£170£145£149£161£147£121£124£145£216
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Quick stats about holiday rentals with a pool in Simpson Bay

  • Total holiday rentals

    Explore 210 holiday rentals in Simpson Bay

  • Nightly prices starting at

    Simpson Bay holiday rentals start at £60 per night before taxes and fees

  • Verified guest reviews

    Over 4,510 verified reviews to help you choose

  • Family-friendly holiday rentals

    120 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    210 of Simpson Bay holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Simpson Bay rentals

  • 4.8 Average rating

    Simpson Bay stays are highly rated by guests – averaging 4.8 out of 5!