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Holiday houses in Little Bay

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Top-rated holiday rentals in Little Bay

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A wide view reveals the tranquil turquoise waters of Great Bay, framed by lush green hills. A modern tiled railing encircles the spacious deck area, inviting guests to enjoy the scenic landscape. Fluffy clouds drift above the vibrant seascape.
Apartment in Little Bay
4.92 out of 5 average rating, 25 reviews

Great Bay view charming Apt!

This special place with a Beautiful view of Great Bay! Watch the cruise ships come in with coffee and leave at night with a cocktail! . View Phillipsburg boardwalk from your deck. A short walk down the hill to Little Bay Beach.A mile from Front Street boardwalk shopping. Easy free parking on site. Starlink Wi-fi with a smart Tv and Netflix plus A DVD player with many free DvD’s on site.. Nice Caribbean breezes. 7 night minimum . We suggest renting a car for full enjoyment of touring the island.

Top Guest favourite
A bright living area features large glass doors that open to a private outdoor space. A comfortable sofa and a coffee table are positioned on a light-toned rug. A TV is mounted on a sleek white cabinet, while wooden accents add warmth to the design.
Apartment in Simpson Bay
5 out of 5 average rating, 62 reviews

The Loft at Simpson Bay Yacht Club

Welcome to The Loft at SBYC. Located in the heart of Simpson Bay in walking distance to the beach, great restaurants, grocery stores, shopping, salons/spas and more. In this fully renovated loft-style apartment, you will find high quality amenities throughout including a European kitchen and an amazing rainfall shower. The SBYC property offers 3 swimming pools, a hot tub, tennis courts and plenty of outdoor space for relaxing, all under 24-hour gated security. Free concierge service included.

Guest favourite
A vibrant blue gate opens to reveal a sandy beach and calm waters. Decorative pots with blooming pink flowers frame the entrance, accompanied by lush green leaves. In the distance, sailboats can be seen on the horizon under a cloudy sky.
Apartment in Simpson Bay
4.88 out of 5 average rating, 227 reviews

Apartment on the beach

Let this tranquil, centrally located, 1 bedroom apartment become your home away from home. This beachfront property is located on the BEST and WIDEST stretch of Simpson Bay beach with gentle waves and no rocks, which makes it a perfect spot for swimming. Although this property is tucked away, and there are never many people on this part of the beach, it is in a heart of Simposn Bay. Simpson Bay beach offers one of the longest stretches of uninterrupted sandy, white coastline on Sint Maarten.

Top Guest favourite
A serene beach view is captured, showcasing clear turquoise waters meeting powdery white sands. A picnic table sits on the beach, bordered by vibrant green plants and palm trees. Soft clouds drift above under a bright blue sky, completing the tranquil seaside scene.
Apartment in Simpson Bay
4.96 out of 5 average rating, 208 reviews

Lilly's Beach

This is a very SPECIAL SMAll RESIDENCE known as Ocean Edge . Beach Front located directly on beautiful Simpson Bay Beach! Enjoys one of the best locations on the island . Panoramic sea views with your toes in the sand and balmy Caribbean breezes. A clear turquoise sea dazzles in tropical sun, powdery white sands stretching along one of St. Maarten's longest beaches. Apartment with modern amenities and comforts. A perfect vacation spot ! Back up system installed to insure electricity.

Top Guest favourite
Apartment in Simpson Bay
5 out of 5 average rating, 226 reviews

The Beach House Apartment

A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more

Guest favourite
A spacious verandah features a comfortable seating area with a light-colored couch and a dark wicker coffee table. Lush greenery is displayed in a yellow planter, with panoramic views of the hills and bright blue sky in the background.
Home in Indigo Bay
4.78 out of 5 average rating, 187 reviews

La Pearle - Luxurious 1 Bedroom Condo By the Beach

Nestled on the hills of Indigo Bay, La Pearle is located midway between Philipsburg and the Simpson Bay touristic hang out. La Pearle exudes relaxation the minute you walk through the door! Awake to watching the Allure of the Seas make its way into the harbor. La Pearle, elegant, sophisticated and distinguished! The 1- bedroom spacious condo sleeps two! Experience luxury with a huge verandah overlooking the Indigo beach, Caribbean living, yours to enjoy!

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, 174 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 deckchairs, garden furniture, outdoor table and BBQ * Office space * 100 Mbps WiFi * 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, shops and other stores * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

Top Guest favourite
The infinity pool is visibly stretching towards the horizon, blending with the calm turquoise waters of the Caribbean Sea. Palm trees frame the scene, while a cruise ship can be seen cruising in the distance under a clear blue sky.
Apartment in Philipsburg
4.97 out of 5 average rating, 31 reviews

Studio Ocean Front, Infinity Pool

Clearwater is a cliffside waterfront property with one of the most spectacular views on the island! Overlooking Great Bay, Philipsburg, Divi Little Bay, the turquoise Caribbean Sea and the magnificent cruise ships, this one of its kind location will be sure to put you at awe. It is perfectly situated for easy access to all SXM has to offer; restaurants, beaches, grocery stores, downtown shopping, bars and entertainment.

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, 163 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
Loft in Grand Case
4.93 out of 5 average rating, 114 reviews

Beachfront Loft in Grand Case - Sea View

An exceptional beachfront loft on Grand Case Beach, offering majestic ocean views and a prime position above the iconic Rainbow Café. In high season, a stylish and trendy atmosphere sets the tone until about 11 p.m. Sunbeds can be reserved either directly or through us—but guests who book with our help enjoy privileged touches. A luminous, sophisticated retreat steps from Grand Case’s finest venues.

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, 115 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
The calm waters of an infinity pool reflect the clear blue sky, surrounded by vibrant tropical plants and smooth white walls. The gentle curves of the pool edge create a seamless transition into the lush landscape, inviting relaxation and enjoyment.
Guesthouse in Little Bay
4.86 out of 5 average rating, 230 reviews

Your oasis w/ocean view, private pool&hiking track

Long idelness by the infinity pool. Two bedrooms each with their own bathrooms. A few minutes from the beach, shops and nightlife and yet in a quiet, secluded and safe district. The guests has the entire unit with a private pool, a pool deck for sunbathing and a wide porch including a seating and a dining place. The house has a private gated parking.

Popular amenities for Little Bay holiday rentals

When is the best time to visit Little Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$700 NZD$662 NZD$676 NZD$670 NZD$649 NZD$585 NZD$602 NZD$601 NZD$524 NZD$535 NZD$566 NZD$721 NZD
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Quick stats about holiday rentals in Little Bay

  • Total holiday rentals

    Explore 150 holiday rentals in Little Bay

  • Nightly prices starting at

    Little Bay holiday rentals start at $35 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,840 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    100 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    150 of Little Bay holiday rentals include Wi-Fi access

  • Popular amenities for guests

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

  • 4.9 Average rating

    Little Bay stays are highly rated by guests—averaging 4.9 out of 5!