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Holiday houses in Happy Bay

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Top-rated holiday rentals in Happy Bay

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Top Guest favourite
A sandy garden is visible, featuring beach chairs and an umbrella, with a clear view of the beach and sea. A wood deck houses outdoor furniture, illuminated by string lights. Tropical plants surround the area, offering a relaxed atmosphere and easy beach access.
Apartment in Grand Case
4.98 out of 5 average rating, 62 reviews

Best location of the beach! Charming apartment!

This unique and pretty appartment located on the beach, in the heart of Grand-Case has its own little sandy garden, beach chairs and direct beach access . Enjoy a stunning full view on Creole rock and Anguilla. The location in the village and on the beach will make you feel privileged. An Incredible choice of food and entertainment options await you just a short walk away. Groceries, Pharmacy, shopping... New studette on the street side is ready now for two more guests. Pictures coming soon

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, 217 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, 228 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

Superhost
A bright kitchen area features a round white table surrounded by four chairs. Appliances, including a washing machine, are positioned conveniently. An expansive window offers unobstructed views of the sea, and a stylish light fixture adds a contemporary touch to the space.
Holiday home in MONT CHOISY-SAINT MARTIN
4.87 out of 5 average rating, 69 reviews

Mont Choisy "Amazing sea view & Spa" 2BD+Sofa

Relax in this peaceful and elegant accommodation, featuring a private jacuzzi and breathtaking views of the Caribbean Sea, the Dutch side of the island, Terre-Basse, and Anguilla. Enjoy stunning sunsets from your terrace. A well-maintained pedestrian path allows you to reach the idyllic Happy Bay beach and the popular Friar’s Bay beach in just 5 minutes. Ideally located just a few minutes from Grand Case — the island’s culinary hotspot — as well as Marigot and Orient Bay.

Top Guest favourite
A patio area is visible, featuring a private pool beside comfortable loungers, adorned with orange towels. A shaded dining space with a table is positioned near the water's edge, with picturesque views of the bay and surrounding landscape.
Villa in Cul-de-Sac
4.99 out of 5 average rating, 166 reviews

VILLA JADE 1: FEET IN THE WATER/POOL SUITE

VILLA JADE is located in the bay of "FRENCH CUL DE SAC". It is a beachfront complex consisting of 3 private villas. VILLA JADE 1 is a suite for 2 people with a private pool. The villas are quiet and private... your only view is the sea. The bay of "FRENCH CUL DE SAC" is 5 minutes from ORIENT BAY, touristy with restaurants, bars, water activities, but also a few minutes from GRAND CASE, our typical little village with gourmet restaurants by the sea....

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, 179 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
Apartment in Grand Case
4.94 out of 5 average rating, 35 reviews

Modern Apt in Beachfront residence - Hill view

• ⛱️ In a beachfront residence next to the Bleu Émeraude hotel — enjoy a quiet beach out front, with Rainbow Café and other restaurants just a 5–7 minute walk away. • 🌊 Just 60 seconds from door to water. • ✨ Modern, minimalist two-story (staircase) 1BR fully renovated (2025) • Enjoy the beach without paying sea-view prices (save ~50%). On a busy road, but now fitted with premium soundproof windows for peaceful comfort

Top Guest favourite
Home in saint martin
5 out of 5 average rating, 13 reviews

Villa Josefa SXM · Ocean View Above Friar’s Bay

✨ Perched above Friar’s Bay, this villa offers a breathtaking view from Maho to Anguilla. 🏡 3 ocean-view master suites, kitchen ready for a private chef. Upstairs, a covered terrace becomes a peaceful refuge facing the sea for up to 10 guests. 🌊 Pool surrounded by a suspended deck, pergola & evening serenity. 🌴 Gated residence, beaches within walking distance. Here, luxury, nature and sunsets are lived more than described.

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, 167 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
A stunning view of the turquoise sea is visible from a private balcony, featuring a railing with vertical bars. The sandy beach is directly accessible, framed by palm trees and distant hills under a clear blue sky with scattered clouds.
Apartment in Grand Case
4.95 out of 5 average rating, 106 reviews

"Blue beach" On the beach with a AMAZING VIEW

" Blue beach "est un Appartement situé au deuxième étage dans une Résidence les pieds dans l'eau avec une vue exceptionnelle à 180° sur la mer des CARAÏBES et a un accès direct sur la plage de Grand Case. Proche du centre du village bien reconnu pour sa gastronomie , ainsi que de tous les commerces et de l'aéroport coté Français. Idéal pour un couple d'amoureux, entre amis ou pourquoi pas en famille .

Top Guest favourite
Loft in Grand Case
4.93 out of 5 average rating, 119 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.

Guest favourite
A beachfront terrace features modern white lounge chairs and a dining table, overlooking the crystal clear waters. A grill is positioned nearby, and a cooler rests beside an ice bucket, enhancing the inviting coastal experience.
Apartment in Sandy Ground
4.95 out of 5 average rating, 22 reviews

Luxury Beachfront Enclave Unit 2

Luxury brand new beachfront residence directly on beautiful Sandy Ground Beach. This spacious second floor unit is 1,640 square feet. The unit has two terraces, a walk-in shower with handheld & rain shower, a gourmet kitchen, and more. Location is ideal as you can walk to ten plus restaurants. Being on the Caribbean side of the island, the beach is typically always calm & crystal clear.

Popular amenities for Happy Bay holiday rentals

Destinations to explore

  1. Airbnb
  2. Saint Martin
  3. Happy Bay