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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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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
4.83 out of 5 average rating, 24 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.

Top Guest favourite
A bright building is showcased with orange-tiled roofs and white walls, surrounded by lush greenery and palm trees. The structure is positioned along the water's edge, with boats visible in the distance and an inviting view of the bay and surrounding landscape.
Condo in Simpson Bay
5 out of 5 average rating, 44 reviews

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub

A spacious apt in a great location. This apt is located on the 2nd and 3rd floor in a gated +24/7 secured community of the Simpson Bay Yacht Club. A fully stocked kitchen. Open concept Dining/Living room combination leads to a covered patio for outdoor dining with panoramic bay views. 2 large and spacious bedrooms with private baths. Enjoy morning coffee or afternoon cocktails on one of the 3 patios all overlooking water. This complex offers 2 pools, Tennis, Jacuzzi, security and parking.

Guest favourite
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, 8 reviews

Sunny Outlook - 1-bdr condo - Beachfront Residence

✨ Sunny Outlook with IRE Vacations ✨ This amazing 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!

Guest favourite
Apartment in Upper Prince's Quarter
5 out of 5 average rating, 11 reviews

Aman_Sky

The unique Aman_Sky is an oasis of calm, luxury and elegance, built into the hillside overlooking the sublime and sparkling Atlantic Ocean and Saint Barth. This a brand new modern property consists of two master bedrooms with two bathrooms, living room with fully equipped kitchen, exterior terrace and laundry area. All two bedrooms, the living room have unobstructed views of the ocean. A breathtaking infinity pool and a sundeck overlook the ocean, form the focal point of Aman

Top Guest favourite
Condo in Maho
4.9 out of 5 average rating, 239 reviews

Maho Love Shack: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 for you to indulge.

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, 117 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 in Marigot
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

Top Guest favourite
A spacious terrace is furnished with a wooden dining table surrounded by black wicker chairs. Lush greenery and the lagoon are visible beyond the railing, with palm trees swaying gently in the breeze. The sky is bright blue with scattered clouds.
Apartment in Simpson Bay
5 out of 5 average rating, 24 reviews

Vitamin sea 2

Welcome to Vitamin Sea 2 ! This one bedroom condo is well located in Simpson Bay Yacht club, central location in the heart of the action, and nonetheless peaceful atmosphere, tucked away by lush yet elegant landscaping and architecture. The living room and the master bedroom have an amazing view over the lagoon, offering a fresh respite from the town of Simpson Bay. 24/7 security gated residence, swimming pool, parking.

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.
Apartment 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.
Apartment in Little Bay
4.99 out of 5 average rating, 172 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 !

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.
Apartment in Indigo bay
4.94 out of 5 average rating, 123 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.

Guest favourite
An inviting outdoor living space features a covered terrace with comfortable seating, a stylish bar area, and potted plants. The warm wooden flooring complements the soft purple lighting, while ocean views can be seen in the background, creating a relaxing ambiance for gatherings.
Townhouse in Sint Maarten
4.98 out of 5 average rating, 95 reviews

Indigo Bay Villa Poolside - Ocean 14

Experience refined Caribbean living in this enchanting 2-bedroom villa, nestled within the exclusive Indigo Bay community of St. Maarten. This beautifully designed villa offers a perfect blend of comfort, style, and outdoor elegance, making it an ideal retreat for those seeking tranquility and luxury.

Popular amenities for Simpson Bay rentals with a pool

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$435 NZD$466 NZD$466 NZD$391 NZD$334 NZD$343 NZD$370 NZD$338 NZD$279 NZD$286 NZD$334 NZD$497 NZD
Avg. temp26°C26°C26°C27°C28°C29°C29°C29°C29°C29°C28°C27°C

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 $137 NZD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    210 of Simpson Bay holiday rentals include Wi-Fi 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!