Family-friendly vacation rentals in Simpson Bay

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Top-rated family-friendly rentals in Simpson Bay

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Guest favorite

Apartment in Simpson Bay

4.87 out of 5 average rating, 211 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 favorite

Guesthouse in Simpson Bay

4.96 out of 5 average rating, 100 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

Guest favorite

Home in Les Terrasses de Cul de Sac

4.96 out of 5 average rating, 24 reviews

Water access, heated pool, kayaks & snorkeling

Optic fiber wifi, heated swimming pool, tropical garden and private access to the water! Welcome to the magnificent Bay of Cul de Sac, where turtles, pelicans and inhabitants of this paradise share the most extraordinary marine reserve, so shallow that you will walk on the water! The Villa Côté Mer is a stunning, brand new property, overlooking this uncommon and magical bay, and has a direct and private access to the ocean, where kayaks are at your disposal (included in the rental).

Superhost

Apartment in Simpson Bay

4.93 out of 5 average rating, 28 reviews

Apartment Simpson Bay Yacht Club at the Marina

Welcome to our apartment at the Marina in the Simpson Bay Yacht Club. A gated residence with 24 hours security, 2 swimming pools, outdoor jacuzzi, 2 tennis courts. You'll have a direct view over the marina and the Simpson Bay Lagoon. In front of the apartment is a private boat slip! and a private parking space. The apartment is within walking distance from bakeries, lunch rooms, restaurants, pharmacy, medical care, supermarket, night life, and beaches. Check also my other apartments!!

Top guest favorite

Apartment in Simpson Bay

5 out of 5 average rating, 208 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 favorite

Condo in Maho

4.9 out of 5 average rating, 207 reviews

Serene Oasis: Unwind by the Rooftop Pool & Hot Tub

This charming, cozy, and tranquil tropical nest is located where all the action is! The golf course, iconic bars, the unprecedented landing strip, the popular Maho and Mullet bay beaches, Maho market with daily fresh take away breakfast/lunch buffets and a divine selection of exotic restaurants are all in walking distance! If you wish to just lounge and relax by the pool, jacuzzi, and private gazebo bar or enjoy the nightlife; it’s all readily available, at your fingertips!

Superhost

Apartment in Cupecoy

4.95 out of 5 average rating, 65 reviews

Panoramic ocean view Large 3 Bed Rooftop Penthouse

‘Has to be seen to be believed! - ‘a once in a lifetime experience!’ Described by previous guests as 'a portal to another world' and 'a totally zen experience', 'reignited our passions'. Spacious flexible living for up to 3 bedrooms. Recently fully renovated, my place is a luxury penthouse with a large private deck and great panoramic ocean views. There is dining nearby, family-friendly activities, and beaches. Pool, gym and 24hr security with gated parking underground.

Guest favorite

Apartment in Lowlands

4.97 out of 5 average rating, 133 reviews

Cupecoy Côté Jardin 1

Delightful one bedroom appt. Fully furnished with mid century teak furniture. A spacious 70m2 space with large terrace in a mature tropical garden. A brand new fully equipped kitchen was added in October 2022. Located in trendy and safe Cupecoy. CJ1 is a quiet oasis to relax in the luxurious garden, or head for the the renowned beach of Mullet bay within a 3 minute walk. Supermarkets, gym yoga studio very close by. This is the place to be.

Guest favorite

Villa in Collectivité de Saint-Martin

4.95 out of 5 average rating, 60 reviews

Slowlife Harmony - Caribbean Villa Three Bedrooms!

Harmony is your perfect vacation home, will give you the feeling of being at home in the Caribbean, this spacious 3-bedroom Caribbean style villa, we can accommodate a family, couples and friends. Harmony will be your home away from home, and at the same time you will have a personalized service for requests and to guide you with information about all the activities and places that you must experience on our island.

Superhost

Condo in SX

4.83 out of 5 average rating, 116 reviews

Large 2BR Condo - STEPS FROM BEACH!

Experience tropical luxury at our Mullet Bay vacation rental in Sint Maarten. Our 2BR/1BA property boasts queen beds, full kitchen, laundry facilities and a gated community complete with pool and barbecue area. Perfect for families, couples or groups seeking a tranquil escape. Enjoy the comfort of spacious bedrooms and the convenience of on-site amenities. Book now for the ultimate island getaway!

Top guest favorite

Villa in Cul-de-Sac

4.98 out of 5 average rating, 133 reviews

VILLA JADE 2 : SUITE PIEDS DANS L'EAU / PISCINE

VILLA JADE est un complexe de 3 villas situé dans la baie de CUL DE SAC et ses îlets ... VILLA JADE 2 est une suite spacieuse / vue mer pour 2 personnes les pieds dans l'eau, avec piscine privée. Les 3 villas sont mitoyennes mais très calmes et intimes. Votre unique vue est la mer... Accès direct à la mer par un ponton, et kayaks à votre disposition.

Guest favorite

Guesthouse in Little Bay

4.86 out of 5 average rating, 229 reviews

Your oasis with spectacular views and private pool

Long idelness by the infinity pool. Two bedrooms each with its own bathroom and seperate toilette. A few minutes from the beach, shops and nightlife and yet in a quiet and safe area. The guests has the entire home with a private pool. Please check “villa_pi” on instagram for more photos