Family-friendly vacation rentals in Simpson Bay

4.86 out of 5 average rating, 29 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 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, 239 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, 107 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. Satellite TV. Additional Queen sofa sleeper in living room sleeps 2. Washer/Dryer. 90 steps to the beautiful Simpson Bay Beach. Private 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, 228 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, 238 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

An aerial view captures the vibrant landscape of Simpson Bay Yacht Club, revealing the layout of the community, including palm trees, two swimming pools, and tennis courts. The calm turquoise waters border the marina, and the lush green hills rise in the background, complementing the scene.

4.95 out of 5 average rating, 38 reviews

The Pineapple Suite

Discover The Pineapple Suite, a chic 2-bedroom retreat accommodating up to 4 guests, nestled within the secure confines of Simpson Bay Yacht Club's gated community. Unwind in modern luxury, relish on-site amenities like the two swimming pools, tennis courts, bbq area and soak in breathtaking views of the yachts, lagoon, hills and sunset from your balcony. Conveniently located near the airport in Simpson Bay within walking distance from restaurants, the beach, bars and supermarkets.

A spacious terrace is presented with a wooden dining table surrounded by four chairs, complemented by a selection of fresh fruit. Sun loungers are positioned for relaxation, with a view of the turquoise water and sailboats visible in the distance.

5 out of 5 average rating, 147 reviews

Simpson bay beach, spacious, beautiful views!

Amazing spacious 3 bedroom, 2 bathroom apartment with awesome location in the heart of Simpson Bay. location, location, location in the middle of it all. Right across the 2.5 mile beautiful Simpson Bay Beach, it is not directly on the beach but 25 steps away. All the beach necessities are there to enjoy, beachchairs, snorkeling gear, fishing rod and even 2 kayaks. You can walk to many nearby restaurants, grocery stores and other shops. Public transportation is also steps away.

5 out of 5 average rating, 14 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!

4.86 out of 5 average rating, 78 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.

Villa in Upper Prince's Quarter

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.

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.

4.99 out of 5 average rating, 186 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

4.95 out of 5 average rating, 147 reviews

A panoramic ocean view is captured from the terrace featuring a private heated pool. The crystal-clear water of the pool reflects sunlight, while the vast sea and distant islands are visible under a bright blue sky with scattered clouds.

Apartment in Little Bay

Stunning Ocean View - 2 / 3 Brm Terraces Lt. Bay

Treat yourself to the stylish and modern ocean view apartment . This spacious environment, is designed to be enjoyed as a family, has a terrace with stunning sea view, climatized private pool, two master suites (one w/Japanes king bed and walking closet), the other with two double size beds (you can join them and make a king bed) and closet and a third room with daybed. All of them with their own bathroom and ocean view. Welcome!

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

4.91 out of 5 average rating, 125 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

4.88 out of 5 average rating, 32 reviews

A scenic outdoor area features a spacious deck with a hot tub and sun loungers, surrounded by lush greenery. The panoramic view overlooks the vibrant blue sea, framed by rolling hills and a clear sky, providing a sense of tranquility.

Villa in Anse Marcel

Villa with sea view, pool and jacuzzi

4.85 out of 5 average rating, 145 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

Place to stay in Simpson Bay

A compact living area features a wall-mounted Murphy Bed that converts to a sofa, offering flexible space. A kitchenette with a refrigerator and sink is included. Natural light enters through an arched window, complementing the light-colored wood flooring and neutral furnishings.

4.97 out of 5 average rating, 35 reviews

The Hideaway

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, 216 reviews

Bungalow in the lowlands

4.95 out of 5 average rating, 129 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

4.95 out of 5 average rating, 56 reviews

A tranquil swimming pool is surrounded by lush palm trees and vibrant greenery, reflecting a clear blue sky. The marina, filled with docked yachts, creates a serene backdrop, while lounge chairs are positioned beside the water for relaxation.

Condo in Simpson Bay

Studio on the water in the Simpson Bay Yacht Club

4.99 out of 5 average rating, 91 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

Family- and pet-friendly home rentals

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.

4.97 out of 5 average rating, 38 reviews

Brand new! - Slowlife - Enjoy Villa

4.96 out of 5 average rating, 143 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

5 out of 5 average rating, 25 reviews

A shaded outdoor seating area features a comfortable sectional sofa and a natural wood coffee table. Tropical palm trees and a view of the pool enhance the space, while loungers are positioned nearby. Soft textiles in muted colors contribute to a laid-back ambiance.

Home in SAINT MARTIN

The best view on the island!

A living area features a blue sofa against a palm tree mural, complemented by natural wood stools and a woven rug. Large windows invite light and offer access to a private terrace, enhancing the spaciousness of the room.

4.94 out of 5 average rating, 17 reviews

Beacon Hill Apartment Location Beaches, restaurants

5 out of 5 average rating, 16 reviews

Apartment in BAIE NETTLE

Tropical Elegance : Lagoon View Studio

Apartment in Upper Prince's Quarter

5 out of 5 average rating, 15 reviews

Aman_Sky

4.97 out of 5 average rating, 146 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

4.92 out of 5 average rating, 13 reviews

Apartment in Grand Case

NEW: Unmatched Oceanfront Living in Grand Case

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 57 reviews

An outdoor dining area is set for a meal with an expansive table that accommodates eight or more guests. The space features sleek chairs and offers unobstructed views of the ocean and horizon, framed by clear skies. The surrounding area reflects a serene coastal ambiance.

Home in Sint Maarten

Ocean View Villa-Indigo Bay W/Private Pool/0 Steps

5 out of 5 average rating, 27 reviews

The villa features a modern design with two levels, surrounded by lush greenery. An infinity pool is situated in front, with reclining chairs positioned nearby. The outdoor dining area is visible, and the expansive glass windows reflect the vibrant surroundings, inviting natural light into the space.

Villa in Indigo Bay

Life's Good

4.95 out of 5 average rating, 22 reviews

A spacious terrace offers an unobstructed view of the marina at sunset, with soft sunlight reflecting off the water. A chaise lounge is positioned for relaxation, surrounded by lush greenery and floor-to-ceiling windows that enhance the scenic outdoor experience.

Apartment in Cole Bay

Sunny Marina Residence

A stunning view of the turquoise ocean is showcased under a bright blue sky with fluffy clouds. Palm trees frame a peaceful swimming pool located within the complex, enhancing the tropical atmosphere.

4.97 out of 5 average rating, 31 reviews

SeaBliss 3BR Palm Beach Condo Simpson Bay

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.

4.97 out of 5 average rating, 35 reviews

Modern apartment with shared pool and generator

4.8 out of 5 average rating, 20 reviews

A panoramic view of the turquoise sea is captured from the rooftop, with the coastline and palm trees visible in the foreground. Soft white clouds drift over the lush green mountains in the distance, creating a serene backdrop to the vibrant scene.

Home in Simpson Bay

Townhouse Villa LX

4.97 out of 5 average rating, 31 reviews

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.

Condo in Simpson Bay

Ocean Breeze at Las Arenas