Family-friendly holiday rentals in Cole Bay

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.

5.0 out of 5 average rating, 84 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.

KitchenIndoor spacesSolo travel

4.81 out of 5 average rating, 103 reviews

A master bedroom featuring large windows that offer a view of the ocean and sky. Natural light floods the spacious area, highlighting the white bedding on the bed and the elegant design of the room. A modern freestanding bathtub is seen in the corner.

Condo in Philipsburg

Horizon (Apt3) – Sea & Pool View, Terrace

Stylish triplex with 3 bedrooms, all with sea and pool view. Located in Black Palm, an elegant residence of 7 apartments in Indigo Bay, a calm and exclusive neighborhood. Indigo Beach is just a 5-minute walk away. Enjoy the shared pool with sea view. Ideal for up to 5 guests: couples, friends or families looking for relaxation. - 5 minutes’ walk from Indigo Beach - 5 minutes’ drive from the nearest supermarket - Private parking on site - Concierge service available for any request.

Indoor spacesKitchenCondition

5.0 out of 5 average rating, 254 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

KitchenIndoor spacesOutdoor spaces

4.97 out of 5 average rating, 29 reviews

Condo in Simpson Bay

4 Bedroom Beachfront Condo with Private Pool D2.1

Welcome to Kim Sha Beach Front apartment where amazing memories are made! Location is our shining spot! Just mins walking to the beach and located in the busiest area! Surrounded by bars and popular restaurants with local and international food, spas, shops and casinos! Walking distance to Simpson Bay Marina where you have departures to different islands with numerous boat charter and water sports activities. The location assures that you will have an unforgettable holiday!

Indoor spacesFamilyNearby

4.96 out of 5 average rating, 153 reviews

A serene beachfront view is presented through sliding glass doors, showcasing a private terrace with a small round table and two chairs. Palm trees gently sway in the breeze, framing the clear turquoise sea and sandy beach beyond.

Condo in Marigot

"SeaBird" studio, feet in the water on the beach

The "SeaBird studio" is ideally located with a beautiful view of the Caribbean Sea and an idyllic beach just for you! It offers plenty of comfort and storage with refined and original decoration. The residence is perfectly secure with a large swimming pool and tropical garden. Everything is within walking distance: grocery store, local market, shops, traditional or gourmet restaurants, ferry station to other islands, etc... High-speed Wi-Fi and TV Europe and America.

KitchenFamilyPool

5.0 out of 5 average rating, 201 reviews

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

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

Indoor spacesFamilyNearby

4.86 out of 5 average rating, 159 reviews

A modern living area features a comfortable gray sofa and a wooden dining table with two chairs. A decorative plant adds a touch of greenery. On the wall, a piece of artwork depicts an abstract scene, while a television is mounted on a white shelf across from the seating.

Apartment in Cole Bay

J-m house 2

Welcome to the “Friendly Island” of Sint Maarten, a Caribbean gem where the sun shines all year round and hospitality is a true tradition. Here, we welcome you to our elegant and harmonious guesthouse, thoughtfully designed for your comfort and well-being. From the moment you arrive, you’ll be charmed by the warm and soothing atmosphere. Every space has been carefully crafted, with everything you need to make you feel instantly at home.

Indoor spacesFamilyParking

4.85 out of 5 average rating, 158 reviews

A dining area is presented with a modern table surrounded by four black chairs. Above, a colorful artwork adorns the wall, complementing the vibrant decor. Two candles on the table add an elegant touch, while soft lighting from above enhances the welcoming ambiance.

Condo in Cole Bay

Convenient, Near Airport, Free Parking + Security.

Cozy 1 bedroom apartment that is centrally located in a gated community in Cole Bay. This area is situated on the Dutch side of the island, but it is near the French side of the island. The apartment is 10 minute drive from the Princess Juliana International Airport. In the area, there is a small supermarket which is 1 minute walking distance and Lagoonies Bistro & Bar which is 2 minute walking distance from the apartment.

KitchenIndoor spacesCheckout

Villa in Indigo bay, Sint Maarten

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.

4.93 out of 5 average rating, 73 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.

KitchenIndoor spacesBathroom

4.99 out of 5 average rating, 189 reviews

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

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 !

Indoor spacesFamilyHospitality

4.99 out of 5 average rating, 105 reviews

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

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.

FamilyKitchenBeach

5.0 out of 5 average rating, 61 reviews

Home in Cole Bay

Spacious 3BR with Private Cozy Pool

This spacious 3-bedroom, 2.5-bathroom home with its own private pool is the perfect retreat for those seeking a luxurious yet cozy getaway. The home is centrally located Cole Bay. It sleeps up to 6 guests and features a private backyard, a fully equipped kitchen and a short drive to beaches, restaurants and supermarkets.

Indoor spacesKitchenCheck-in

Popular amenities for Cole Bay family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A spacious outdoor lounge area is featured, with white sofas adorned with blue cushions. The view includes vibrant ocean hues and palm trees swaying gently. A dining table is positioned in the background, offering a scenic space for alfresco meals.

4.95 out of 5 average rating, 113 reviews

Top of the art penthouse

KitchenFamilyCleanliness

4.91 out of 5 average rating, 258 reviews

Condo in Maho

Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub

KitchenIndoor spacesQuiet

4.93 out of 5 average rating, 211 reviews

Guest suite in Cole Bay

Indigo Sweet

FamilyKitchenQuiet

4.85 out of 5 average rating, 157 reviews

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

Villa Bella sea view pool and jacuzzi 3 bedrooms

Indoor spacesKitchenComfort

Guesthouse in Saint Martin

4.9 out of 5 average rating, 226 reviews

Bungalow in the lowlands

KitchenIndoor spacesPool

Apartment in Saint Martin

An octagonal jacuzzi is positioned on a wooden deck, surrounded by lush greenery. Two lounge chairs are placed nearby, providing a comfortable seating area. The view overlooks a scenic landscape with hints of distant hills under a bright sky, creating a serene outdoor ambiance.

4.92 out of 5 average rating, 106 reviews

The Perch - A unique jungle experience.

FamilyIndoor spacesValue

4.95 out of 5 average rating, 143 reviews

A scenic view reveals a large swimming pool surrounded by lounge chairs and colorful flower gardens. The sparkling blue ocean and a distant boat can be seen, under a bright sky with fluffy clouds. Palm trees gently sway in the breeze, adding to the tropical ambiance.

Condo in Lowlands

Saint Maarten La Terrasse Maho

Indoor spacesFamilyParking

4.91 out of 5 average rating, 141 reviews

An infinity pool extends over the edge, offering panoramic views of the lagoon. The tranquil water reflects the blue sky, while steps lead from the pool's edge to the terrace. Lush greenery is visible, enhancing the serene atmosphere of the space.

Guest suite in Cupecoy

Panoramic View Terrace Infinity Pool Top Penthouse

KitchenFamilyHospitality

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 153 reviews

An outdoor wooden deck terrace features two lounging chairs, surrounded by lush greenery. Natural light filters through the open sliding door, leading into the studio interior. A surfboard serves as a decorative element against the wall, adding a touch of character to the space.

Apartment in Lowlands

Garden Side 2 Large Studio

KitchenFamilyLaundry

Apartment in Upper Prince's Quarter

A modern kitchen with a sleek countertop offers an unobstructed view of the ocean through large glass doors. The space includes a coffee maker, a fan, and cooking amenities, while the living area beyond is furnished with a dark sofa and bright decorative accents.

4.89 out of 5 average rating, 104 reviews

Relaxing Hideaway w/ Great Views

FamilyIndoor spacesCondition

Guest suite in Simpson Bay

A cozy sitting area is showcased, featuring a round coffee table surrounded by two comfortable chairs and a small dining table. A decorative mirror reflects light, while a lamp provides additional warmth. Artwork adorns the wall, contributing to the space's aesthetic.

4.82 out of 5 average rating, 233 reviews

MYRIEL — Perfect Location/Nightlife/Beach

KitchenFamilyNearby

4.94 out of 5 average rating, 142 reviews

Loft in Grand-Case

Beachfront Loft in Grand Case - Sea View

Indoor spacesKitchenNearby

4.86 out of 5 average rating, 168 reviews

A view of a sandy beach with crystal-clear turquoise waters. Gentle waves are visible lapping at the shore. A few boats can be seen in the distance against a backdrop of a bright blue sky dotted with fluffy clouds. Lush green foliage frames the scene.

Condo in Saint Martin

2 Bedroom Duplex up to 5 guests right on the beach

Indoor spacesFamilyLocation

5.0 out of 5 average rating, 126 reviews

A panoramic view of turquoise waters showcases numerous boats anchored in the distance, framed by lush palm trees. A rainbow appears across the sky, adding a colorful touch to the serene coastal landscape.

Townhouse in Cole Bay

Hillside Beach Townhouse Simpson Bay

FamilyIndoor spacesAccuracy

Guest suite in Cul-de-Sac

A serene outdoor space is featured, showcasing a rectangular pool surrounded by wooden decking. A decorative feature resembling a statue is centrally placed against a white wall. Lush greenery is visible nearby, enhancing the privacy of the tranquil environment.

4.93 out of 5 average rating, 121 reviews

Cozy apartment, private pool & terrace

FamilyKitchenCheckout

4.95 out of 5 average rating, 22 reviews

A spacious living area is characterized by arched doorways allowing natural light to fill the room. A round dining table sits centered, with white chairs and a decorative wooden stool nearby. A neutral sofa and a hanging punching bag are visible, inviting relaxation.

Apartment in Cole Bay

Les Alysés - 2BR-private pool

KitchenIndoor spacesTV

Family-friendly home rentals with a pool

A panoramic view of the azure ocean is captured, dotted with sailboats. The sandy beach features thatched umbrellas and lounge chairs. Lush palm trees are visible, alongside a beachside bar area with shaded seating, all under a bright sky with fluffy clouds.

4.92 out of 5 average rating, 66 reviews

Royal Palm Hilton SXM

FamilyKitchenLaundry

4.7 out of 5 average rating, 46 reviews

A sleek, reflective pool extends towards the horizon, capturing the vibrant sunset. Lush greenery frames the view, adding a natural element to the scene. The setting creates a peaceful ambiance, inviting relaxation amidst the beauty of the surrounding landscape.

Villa in Cole Bay

A heavenly Sint Maarten's retreat

FamilyIndoor spacesWi-Fi

4.83 out of 5 average rating, 18 reviews

Villa in Indigo Bay

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

Indoor spacesPoolCondition

5.0 out of 5 average rating, 5 reviews

Apartment in Cole Bay

Beautiful 3 bedroom condo with a private pool

FamilyIndoor spacesGetting around

5.0 out of 5 average rating, 26 reviews

Apartment in Pelican

Luxurious Hidden Pearl - Private Pool

Indoor spacesKitchenCleanliness

4.98 out of 5 average rating, 40 reviews

A modern living area features large floor-to-ceiling windows that offer panoramic views of the ocean and beach. A light-colored sofa is positioned beside a small wooden table, while a plant adds a touch of greenery. Natural light brightens the space, creating an inviting ambiance.

Apartment in Cupecoy

Stunning oceanfront condo

Indoor spacesFamilyAmenities

4.91 out of 5 average rating, 55 reviews

An outdoor dining area is displayed, featuring a white table set with blue glassware. Purple chairs provide seating, while panoramic views of the Caribbean Sea and rolling green hills are visible beyond the patio, showcasing the tranquility of the surrounding landscape.

Villa in Indigo Bay

Villa Elysian in Indigo Bay

Indoor spacesFamilyLocation