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Villa holiday rentals in Simpson Bay

Find and book unique villas on Airbnb

Quick stats about villa rentals in Simpson Bay

  • Total holiday rentals

    Explore 30 holiday rentals in Simpson Bay

  • Nightly prices starting at

    Simpson Bay holiday rentals start at $306 NZD per night before taxes and fees

  • Verified guest reviews

    Over 560 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Wi-Fi availability

    30 of Simpson Bay holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Simpson Bay rentals

  • 4.8 Average rating

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

Top-rated villa rentals in Simpson Bay

Guests agree: These villas are highly rated for location, cleanliness and more.

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Guest favourite
A private pool is bordered by a spacious patio area, featuring two lounge chairs. Expansive ocean views are visible in the background, with lush greenery surrounding the space. A dining table is situated under a covered area, providing a shaded option for meals outdoors.
Villa in Indigo Bay
4.95 out of 5 average rating, 81 reviews

Villa Ocean - Indulge Yourself in Paradise

A three-bedroom, two-bathroom beauty overlooking beach/vast views of the ocean in Indigo Bay. Sunset viewing on the deck, private pool or down to the beach 10 min by walking. 10 min to airport, night life, other popular beaches. Close to town. groceries, restaurants. All the bedrooms have a view of beach and the ocean. There is free wireless internet, TV, air conditioning, a dishwasher, refrigerator, microwave, wine refrigerator, coffee maker, washer dryer, outdoor gas grill and private parking.

Guest favourite
A private pool is situated on a wooden deck, surrounded by lush greenery and palm trees. Sun loungers are positioned nearby, offering a view of the sea and distant boats. The clear water of the pool reflects the vibrant blue sky.
Villa
5.0 out of 5 average rating, 110 reviews

VILLA I LOVE VIEW - villa luxe avec vue mer

Villa I LOVE VIEW est une oasis de tranquillité – avec sa piscine privative (naturisme possible), sa grande terrasse et son espace de cuisine luxueux. Venez découvrir sa vue aux multiples nuances de bleues en vous relaxant sur les transats au bord de la piscine aux reflets pierres naturelles zen Située à Cul de Sac, face à Saint Barth , l'ilet Pinel et la Baie Orientale. A proximité des plus belles plages de l'ile, restaurants, divertissements nautiques, c'est le lieu idéal pour vos vacances.

Guest favourite
A private pool is framed by wooden decking, complemented by two lounge chairs and a side table. A scenic view of azure waters and distant islands is visible, with sailboats dotting the horizon. Lush palm trees provide a tropical ambiance.
Villa in Cul-de-Sac
4.85 out of 5 average rating, 156 reviews

Villa Bella vue mer piscine et jacuzzi 3 chambres

Réveillez-vous chaque matin face à l’île Pinel, dans une villa moderne baignée de lumière, avec piscine privée et un environnement calme et verdoyant. La Villa est située dans la residence Horizon Pinel vue sur îlet Pinel, petite Clef, Orient Bay, Tintamarre et Saint Barthélemy. Elle donne vue sur l'incroyable et célèbre réserve naturelle de la baie de Cul de Sac, connue pour sa population de tortues, raies et pélicans. La baie peu profonde et toujours calme est idéale pour le snorkeling

Top Guest favourite
Villa in Upper Prince's Quarter
4.94 out of 5 average rating, 87 reviews

Villa Blue Roc

Cette villa luxueuse , est situee dans une residence securisee avec une vue epoustouflante , face a l ocean et l ile de St Barthelemy, Perchee sur les hauteurs de Dawn Beach, a 15 minutes des fameuses plages/restaurants d Orient Bay et Grand Case en partie francaise. La villa est egalement a 5 minutes de la capital hollandaise , Philipsburg, un incontournable du shopping. Grace aux grands espaces exterieurs et a la piscine a debordement , cette villa vous offrira un sejour inoubliable.

Superhost
Villa in Indigo Bay
4.82 out of 5 average rating, 17 reviews

AZUR 4BR 4.5BA Walk to Indigo Beach- Sea Side Dr.

Welcome to AZUR, the newest luxury villa at Indigo Bay, Sint Maarten. Stunning property features 4 BR, 4.5 BA each with a king bed, and en-suite full baths and fitted wardrobes. Guests can enjoy inside and outside dining, each room controlled AC , WiFi, Infinity pool, 3 large terraces, BBQ grill, rooftop lounge, tropical garden, turquoise sea, and sunsets. This captivating spacious villa has gourmet kitchen with island for casual dining. AZUR is your exclusive sanctuary by the sea.

Top Guest favourite
A stunning sunset is captured over the calm sea, reflecting vibrant colors onto the water's surface. In the foreground, a serene pool mirrors the sky, enhancing the tranquil ambiance of the outdoor space. The silhouette of trees adds a natural element to the scene.
Villa in Simpson Bay
4.97 out of 5 average rating, 91 reviews

Waterfront "Bonjour" Beacon Hill St Maarten

This stunning 4-bedrooms, 4 bathrooms villa overlooks Maho Bay and provides a front row seat to beautiful SXM sunsets, and over the famous Maho Beach. Enjoy the views while taking a dip in the home’s infinity pool overlooking the ocean or from its multiple outdoor dining and seating options conveniently and securely located minutes from restaurants, bars, nightlife, Maho Market and more, steps away from direct beach access to Simpson Bay Beach. Back up Diesel Generator

Superhost
A modern villa exterior is displayed under a clear blue sky. Sleek white walls are complemented by well-maintained landscaping and palm trees. An outdoor lounge area is visible, featuring comfortable seating and a shaded area for relaxation.
Villa in Simpson Bay
4.87 out of 5 average rating, 86 reviews

Modern 2 bedroom luxury beachside villa with pool

Your own private paradise. Modern 2 bedroom luxury villa in safe gated community with security. New appliances with air conditioning, WIFI, security cameras, and secured free parking including Smart TV with free NetFlix, HBO Max, and Prime access. Private pool with adjacent outdoor dining/lounge area. Perfect for families or couples. Maid and private chef service available if needed. Walking distance from dining, night clubs, and shopping. Steps away from the beach.

Guest favourite
An infinity pool is visible in the foreground, its clear water merging with the expansive blue sea. Beyond, the horizon features distant islands under a clear sky, complemented by palm trees swaying gently in the breeze.
Villa
4.84 out of 5 average rating, 91 reviews

Villa Indigo Dream, Indigo Bay SXM

Prepare to de-stress and to be mesmerized by the continuous influence of the sunlight and the sea throughout the villa. The villa offers a spectacular indoor-outdoor living experience which opens onto the infinity pool deck and boasts breathtaking views of the islands Saba, St. Eustatius and St.Kitts. The home defines true tranquility. Listen to the surf as sip your coffee in the morning or make a sunset toast watching nature's greatest light show over the sea.

Guest favourite
A private pool is set in a serene outdoor area, surrounded by lush greenery and palm trees. The pool features a tiled edge, with a wooden tray holding tropical fruits floating in the clear water. A spacious lawn complements the inviting atmosphere.
Villa in Indigo bay, Sint Maarten
4.94 out of 5 average rating, 71 reviews

Ocean Dream Villa

Indulge in luxury at a two-bedroom villa in Indigo Bay, Sint Maarten. Enjoy modern elegance, a private pool, and ocean views. Relax indoors or outdoors, savor gourmet meals, and unwind under starlit skies. Luxurious bedrooms offer ocean vistas. Whether for romance or family, this villa promises a memorable Caribbean escape at Ocean Dream, where luxury meets natural beauty. Book now for an extraordinary island retreat.

Guest favourite
Villa in Lowlands
4.77 out of 5 average rating, 152 reviews

SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay

Sea View Luxury Villa Perfect for Girls Getaways & Birthday Celebrations Maho Village Celebrate in style at this stunning Sea True villa, custom designed with high end finishes and built for an unforgettable immersive sensorial experience. With 5.8 meter vaulted ceilings a private pool and every amenity you could dream of. It’s the ultimate escape for groups and special occasions.

Guest favourite
An outdoor seating area features a black wicker sofa with colorful cushions. Nearby, a private pool glistens under the sun, surrounded by lush greenery. The terrace's wooden flooring leads to steps down to the pool, offering a relaxing space to enjoy the warm weather.
Villa in Koolbaai
5.0 out of 5 average rating, 18 reviews

Sol y Mar - Beachfront Penthouse with private pool

✨ Sol y Mar with IRE Vacations ✨ Beautiful beach penthouse Sol Y Mar is located in the heart of Simpson Bay. Sol Y Mar is steps away from the popular Kimsha beach, as well as many restaurants and activities of the area. This beach penthouse sits in the midst of it all. Ideal if you are looking to be within walking distance to supermarkets, restaurants, bars, clubs & watersports.

Top Guest favourite
A private outdoor area features a swimming pool surrounded by lounge chairs, with views of the water and distant hills. Palm trees provide shade, while a wooden structure offers a dining space. Natural stone tiles create a welcoming atmosphere, ideal for relaxation.
Villa in Cul-de-Sac
4.99 out of 5 average rating, 160 reviews

VILLA JADE 2 : SUITE PIEDS DANS L'EAU / PISCINE

VILLA JADE est un complexe de 3 villas situé dans la baie de CUL DE SAC et ses îlets ... VILLA JADE 2 est une suite spacieuse / vue mer pour 2 personnes les pieds dans l'eau, avec piscine privée. Les 3 villas sont mitoyennes mais très calmes et intimes. Votre unique vue est la mer... Accès direct à la mer par un ponton, et kayaks à votre disposition.

Popular amenities for Simpson Bay villa rentals

When is the best time to visit Simpson Bay?

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Avg. price$3,412 NZD$2,628 NZD$2,628 NZD$2,259 NZD$1,995 NZD$2,020 NZD$2,075 NZD$1,935 NZD$1,935 NZD$1,935 NZD$1,935 NZD$2,755 NZD
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