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Villa holiday rentals in Simpson Bay

Find and book unique villas on Airbnb

Top-rated villa rentals in Simpson Bay

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

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Top 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, 76 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.

Top Guest favourite
Villa in Philipsburg
5 out of 5 average rating, 9 reviews

Ocean View Villa Little Bay

🌴 Villa Little Bay – Oceanview Bliss With 360° Views Enjoy the peaceful sound of the waves and a serene, private atmosphere that’s still close to everything. We’re located within walking distance to Philipsburg, the vibrant heart of SXM—Front Street, top shopping, restaurants, and the island’s best casinos. The beach is just 5 minutes away, Step outside to your private patio for sunbathing, and shimmering ocean‑view pool. Villa offers the perfect blend of tranquility and convenience.

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
4.86 out of 5 average rating, 78 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
The private pool features clear blue water, surrounded by lounge chairs and lush tropical greenery. An expansive view of the ocean is visible in the background, complemented by a bright blue sky and scattered clouds.
Villa in Pelican Key
5 out of 5 average rating, 33 reviews

Villa Zircon in Pelican Key awaits you - Generator

Gorgeous 4 bedroom - 4 bath villa in the heart of Pelican. This luxurious villa has a beautiful private pool with stunning ocean views and sleeps up to 10 people. It has 4 bedrooms and each bedroom has its own bathroom. 2 lounge areas inside, a dining area and of course all the seating outside on the deck to enjoy the sun, the breeze and the incredible views! We look forward having you. Add my listing to your wishlist by clicking the❤️ in the upper right corner.

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, 118 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.

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, 145 reviews

Villa Bella sea view pool and jacuzzi 3 bedrooms

Wake up every morning facing Pinel Island, in a modern villa bathed in light, with a private pool and a quiet and green environment. The Villa is located in the Horizon Pinel residence overlooking Îlet Pinel, Petite Clef, Orient Bay, Tintamarre and Saint Barthélemy. It overlooks the incredible and famous Cul de Sac Bay Nature Reserve, known for its population of turtles, rays and pelicans. The shallow and always calm bay is ideal for snorkeling

Guest favourite
An outdoor space features a private pool surrounded by lounge chairs and a dining area with a large table. Palms sway gently in the breeze, framing views of the turquoise waters and lush hills. The deck is paved with light-colored tiles, enhancing the serene atmosphere.
Villa in Cul-de-Sac
4.95 out of 5 average rating, 128 reviews

VILLA JADE3: 2 BEDROOMS & POOL FEET IN THE WATER

VILLA JADE is a complex of 3 villas, on the waterfront. VILLA JADE 3, our 2 bedroom villa is located in Cul de Sac Bay, facing PINEL Island and the turquoise water nature reserve. Life is peaceful there, kayaking, relaxing, BBQ... You are 5 minutes from the fabulous Baie Orientale, its restaurants, bars and water activities... The 3 villas are adjoining but very private and quiet, your only view is the sea... your only goal is to "enjoy"......

Top 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, 23 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.

Top Guest favourite
A heated pool is surrounded by a bright tiled patio, featuring two people on colorful chicken floaties. The backdrop offers expansive ocean views under a clear blue sky, with scattered clouds enhancing the tranquil atmosphere.
Villa in Sint Maarten
5 out of 5 average rating, 31 reviews

Beach-Private Pool-2 Master King Bedrooms

Get away from your everyday stress and let the breathtaking views of the Caribbean Sea wash it all away as you enjoy the incomparable blue hues of the sea. Unwind in two sublime master suites, each boasting an inviting king-size bed and private bathrooms where you can melt away your worries like never before. Slip into total relaxation with every dip in a heated pool within a breathtaking courtyard—all at your own leisure!

Top 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
4.96 out of 5 average rating, 57 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.

Top Guest favourite
A panoramic view captures the serene turquoise waters of Great Bay, framed by rolling hills and lush greenery. The horizon features a blend of clouds and sunlight, creating a tranquil coastal atmosphere. Cruise ships are subtly visible along the shoreline.
Villa in Little Bay
4.99 out of 5 average rating, 91 reviews

Barefoot Villas GreatBay View in Hot Tub & Balcony

Wake up to stunning panoramic views of Philipsburg and Great Bay. Sip your morning coffee as cruise ships glide into port, all while soaking in the refreshing ocean breeze. This centrally located property puts you just minutes away from Philipsburg’s vibrant shopping scene, local supermarkets, restaurants, and some of the island’s best beaches.

Top Guest favourite
An infinity pool extends toward the horizon, offering uninterrupted views of the Caribbean sea. The clear blue water reflects the sky, creating a serene atmosphere. Gentle slopes of greenery frame the scene, with a distant island visible on the water's surface.
Villa in Philipsburg
4.99 out of 5 average rating, 317 reviews

Villa Dream View Belair Sint Maarten SXM

Embrace the tranquility in a friendly tropical caribbean modern designed private villa with spacious rooms that are sure to keep you comfortable and feeling at home. Enjoy the sunny day with infinity pool overlooking caribbean sea or enjoy the sea view while watching the sailing huge cruise ships.

Popular amenities for Simpson Bay villa rentals

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$2,901 NZD$2,901 NZD$2,780 NZD$2,275 NZD$2,064 NZD$2,064 NZD$2,064 NZD$1,925 NZD$1,925 NZD$1,925 NZD$1,925 NZD$2,741 NZD
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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 $406 NZD per night before taxes and fees

  • Verified guest reviews

    Over 510 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, 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!