Family-friendly vacation rentals in Simpson Bay

A spacious daybed is shaded by a wooden pergola, surrounded by vibrant greenery. The beach and ocean serve as a backdrop, with gentle waves lapping at the shore. Colorful cushions and a soft blanket add comfort, while a small Buddha statue creates a serene ambiance.

4.97 out of 5 average rating, 106 reviews

Beach front luxury! Huge 2BR that has it all! 😍🤩😍

5 star hotel luxury is yours in this modern beach home! 2 guest rooms with en-suite bathrooms and deck access. Enjoy cooking your own meals and dine inside or on the deck (or beach!). Largest deck on Simpson Bay beach has it all: huge daybed, loungers, living and dining areas for your comfort and pleasure. Unwind in the den and enjoy the big screen there or in either bedroom. Your neighbor is a boutique hotel and will gladly serve you meals and drinks right to your deck! Much more info available

4.85 out of 5 average rating, 40 reviews

The private patio features a saltwater pool with ocean views, complemented by lounge chairs and tropical plants. Soft clouds drift overhead, enhancing the serene atmosphere. Nearby, a dining area offers an inviting space for meals while overlooking the lush garden and the expansive sea.

Home in Cole Bay

Luxury Villa Turquoise Heaven in Pelican Key

Welcome to Villa Turquoise Heaven- Modern Luxury in Pelican Key, SXM Experience the pinnacle of Caribbean elegance at Villa Turquoise Heaven, the newest luxury villa in the exclusive Tepui Residence. Designed for relaxation and style, this modern retreat offers a seamless blend of indoor-outdoor living with unparalleled views of the turquoise Caribbean Sea. From waking up to the gentle sound of waves to savoring sunsets from your private infinity pool, Villa TH offers an unforgettable escape.

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 out of 5 average rating, 76 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.

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.

4.88 out of 5 average rating, 242 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.

Guesthouse in Simpson Bay

A modern two-story apartment structure features a covered balcony with seating for two. The exterior includes colorful accents and is surrounded by lush greenery. The parking area is enclosed by a wooden fence, accommodating multiple vehicles beneath the home.

4.95 out of 5 average rating, 108 reviews

Simpson Bay Beach 1 bed Apt Topdeck. Ocean views

Modern 1 bedroom luxury apartment detached from the main house. Backup power Generator. Marble floors throughout. All stainless appliances in a full size kitchen. Free WIFI inside and on roof deck. Live TV/ movies. Additional Queen sofa sleeper in living room sleeps 2. Washer/Dryer. 90 steps to the beautiful Simpson Bay Beach. Roof deck with 360° views. Grill, fridge and sink on deck. Beach chairs, beach towels umbrella, coolers. Parking right outside your gate. Onsite massage available.

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.

4.95 out of 5 average rating, 234 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.

5 out of 5 average rating, 244 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

A light-filled living space features a comfortable beige sofa set, complemented by natural wood accents. Large windows provide a view of the ocean, while a doorway opens to an outdoor space adorned with greenery. Simple decor enhances the tranquil atmosphere of the room.

4.96 out of 5 average rating, 103 reviews

Hamaka condo, a beachfront retreat on Simpson Bay

Escape to the ultimate beachfront retreat at Hamaka, a fully equipped condo recently renovated to offer the perfect private beach escape with easy walking distance access to restaurants, bars, and nightly entertainment in Simpson Bay, Saint-Martin. Experience waking up to the sound of the waves and having your morning drink to the sight of the endless shades of the ocean. At the end of your day, unwind and enjoy the magnificent sunsets that this beautiful island has to offer.

4.87 out of 5 average rating, 82 reviews

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

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.

4.99 out of 5 average rating, 193 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

A living room area features comfortable seating with colorful cushions against light blue walls. A dining table is set with breakfast items, including orange juice and pastries. Large windows allow natural light to illuminate the space, providing a view of the terrace and surrounding greenery.

4.99 out of 5 average rating, 101 reviews

Second Home Beach Apartment

Our SECOND HOME beach apartment is truly designed as a second home. A place to where we can escape from the world and reconnect with ourselves. It has all the amenities one needs, like a comfortable living room, high quality mattress and linens, cozy sitting on the terrace to watch the sunset, fully equipped kitchen, and airconditioning in each room. It is located just two houses away from the beautiful white sand beach of Simpson Bay.

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.

4.95 out of 5 average rating, 64 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.

Popular amenities for Simpson Bay family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A bright building is showcased with orange-tiled roofs and white walls, surrounded by lush greenery and palm trees. The structure is positioned along the water's edge, with boats visible in the distance and an inviting view of the bay and surrounding landscape.

4.98 out of 5 average rating, 50 reviews

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub

4.92 out of 5 average rating, 131 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

4.85 out of 5 average rating, 149 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

4.92 out of 5 average rating, 103 reviews

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.

Apartment in St Martin

The Perch - A unique jungle experience.

4.95 out of 5 average rating, 133 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

Guesthouse in Saint Martin

A spacious bedroom features a king-size bed with neutral bedding and decorative pillows. Floor-to-ceiling mirrors create a sense of openness, while a wooden vanity and a stylish chair add functional elements. Warm lighting enhances the overall ambiance.

4.9 out of 5 average rating, 221 reviews

Bungalow in the lowlands

4.99 out of 5 average rating, 96 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

4.95 out of 5 average rating, 133 reviews

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

Independent apartment at the bottom of the villa – Indigo Bay

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 86 reviews

A serene pool reflects the vibrant colors of a sunset, with bougainvillea blossoms floating gently on the water's surface. Lush green foliage frames the view, creating a peaceful atmosphere that invites relaxation.

Villa in Simpson Bay

Waterfront "Bonjour" Beacon Hill St Maarten

4.99 out of 5 average rating, 105 reviews

A spacious outdoor terrace is furnished with comfortable wicker seating and a dining table, providing panoramic views of the ocean and landscape. The inviting overflow pool is visible nearby, surrounded by lush greenery and vibrant tropical plants, creating an ideal space for relaxation and social gatherings.

Villa in MF

Your Paradise Villa

4.67 out of 5 average rating, 178 reviews

Condo in Maho

Maho Beach Ocean View Corner Suite

4.94 out of 5 average rating, 137 reviews

Loft in Grand Case

Beachfront Loft in Grand Case - Sea View

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.

4.94 out of 5 average rating, 109 reviews

Cozy apartment, private pool & terrace

4.96 out of 5 average rating, 151 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

4.8 out of 5 average rating, 142 reviews

A private balcony offers unobstructed views of the tranquil Caribbean Sea, with a sandy beach visible below. A simple table and chairs are positioned on the balcony, allowing for relaxed outdoor seating. Nearby, colorful beach bar structures can be seen along the shore.

Apartment in Philipsburg

1-BR Beach Front Ocean Condo

4.94 out of 5 average rating, 31 reviews

Apartment in Cole Bay

Lovem

Family-friendly home rentals with a pool

Apartment in Upper Prince's Quarter

4.97 out of 5 average rating, 35 reviews

Aman_Aria

A tranquil pool area is surrounded by lush greenery, with tropical plants framing the space. Sun loungers with vibrant blue cushions are positioned along the pool's edge. Natural stone walls provide a rustic backdrop, harmonizing with the serene atmosphere.

4.93 out of 5 average rating, 41 reviews

Modern apartment with shared pool and generator

Villa in Les Terres Basses

An infinity pool with crystal-clear water extends alongside the terrace, offering views of the lagoon and surrounding landscape. Palm trees and sun loungers can be seen at the water's edge, with blue skies and fluffy clouds reflecting on the water's surface.

4.98 out of 5 average rating, 44 reviews

Brand new! - Slowlife - Enjoy Villa

4.73 out of 5 average rating, 22 reviews

2 Bedroom Beachfront Condo with Private Pool D 1.1

A serene view of the infinity pool overlooking the ocean, with lush greenery framing the scene. Relaxed guests can be seen sitting at the pool's edge while boats drift in the distance. Gentle waves create a calming visual of the beachfront setting.

4.97 out of 5 average rating, 32 reviews

Ocean Breeze at Las Arenas

4.86 out of 5 average rating, 7 reviews

Home in Saint Martin

New "The Beach House"

A panoramic view of Simpson Bay beach is visible, with soft sandy shores meeting clear turquoise waters. Several anchored boats dot the horizon under a bright sky adorned with fluffy clouds. Sun loungers are arranged neatly along the beach, inviting relaxation.

4.92 out of 5 average rating, 24 reviews

On the Sea - Beachfront 3 bedroom on Simpson Bay