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Family-friendly holiday rentals in Simpson Bay

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Simpson Bay

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Flat

4.86 out of 5 average rating, 197 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.

Guest favourite

Flat

4.91 out of 5 average rating, 76 reviews

James Hughes nice place 2 bedroom upstairs

James Hughes apartment located in West end affordable and comfortable. we are close to maundays Bay Beach, shoal Bay West Beach, Barnes Bay beach, meads Bay Beach. we are also close to best buy supermarket. close to picante restaurants. excellent wifi. we have cars for rent $35per day we only take cash. we will take you back to the ferry or airport for free. Electric bikes for rent $25 per day. we also have scooters for rent $30per day. we can take you to the beaches and pick you up $30

Guest favourite

Flat

5 out of 5 average rating, 193 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

Home

5 out of 5 average rating, 3 reviews

Villa Twin Palms

Twin Palms’ offers a unique opportunity to enjoy your own private & luxurious tropical villa while enjoying breathtaking and endless ocean views. The villa is tucked into the beautiful hillside inside the secluded ‘Dawn Beach Estates'. The tropical garden leads to the beach. This villa is a 2 bedroom ensuite and a studio apartment. The villa can sleep up to 6 guests. You can enjoy this villa by renting 2 or 3 bedrooms the 3rd bedroom is an additional rate of $115 per night.

Guest favourite

Villa

4.95 out of 5 average rating, 101 reviews

VILLA JADE3: 2 BEDROOMS & POOL FEET IN THE WATER

VILLA JADE is a complex of 3 villas , feet in the water. VILLA JADE 3, our 2 bedroom villa is located in the Bay of Cul de Sac, facing the Ilet PINEL and the nature reserve with turquoise waters. Life is peaceful, kayak outings, idleness, BBQ ... You are 5 minutes from the fabulous Oriental Bay, its restaurants, bars and water activities... The 3 villas are terraced but very intimate and quiet, your only view is the sea....your only goal is to " enjoy"......

Villa

4.83 out of 5 average rating, 69 reviews

Villa Allamanda, sublime view, heated hot tub

Villa Allamanda is a very spacious house located in the secure Parc de la Baie Orientale, French side. It offers many assets for holidays for families or groups of friends: * Large terrace with pool, and its HEATED and overflowing JACUZZI * Spectacular view of the bay and surrounding islands * Beach, water activities and shops within a 10-minute walk * 4 bedrooms with private bathrooms * Bluetooth speakers around the pool, with USB charger * Wifi

Guest favourite

Home

4.89 out of 5 average rating, 28 reviews

Luxury, Villa Panoramic Sea Views, Pelican Key

Welcome to Villa del Mar, a luxurious executive home offering breathtaking panoramic views of the Caribbean Sea and stunning sunsets. From this exquisite property, you can see the islands of St. Barts, Nevis, St. Kitts, St. Eustatius, and Saba. Nestled in the premier residential area on the Dutch Side, it provides easy access to vibrant attractions and beautiful beaches while ensuring privacy and tranquility.

Flat

5 out of 5 average rating, 6 reviews

Pelican Key 1BR Townhouse

My place is close to the beach, family-friendly activities, nightlife, public transport, and the airport. You’ll love my place because of the location, the people, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, solo adventurers, business travelers, and families (with kids). Caribbean Weeks has many units all over the island both smaller and larger then this one.

Apartment

4.82 out of 5 average rating, 103 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!

Guest house

4.86 out of 5 average rating, 223 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

Guest favourite

Townhouse

4.97 out of 5 average rating, 32 reviews

Searulean, a stylish 3 bedroom abode in Orient Bay

Welcome to Searulean, the perfect vacation rental in Orient Beach, Saint-Martin for those seeking a luxurious and comfortable stay. This beautiful 3 bedroom townhouse offers exceptional value and is just steps away from the stunning beach and within walking distance to all amenities.

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Popular amenities for Simpson Bay family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Apartment

4.57 out of 5 average rating, 7 reviews

The Cliff, Ocean View Luxury units

Guest favourite

Apartment

5 out of 5 average rating, 36 reviews

The Cliff in Cupecoy Beach HEAVEN!!!

Guest favourite

Flat

4.88 out of 5 average rating, 41 reviews

Amazing 1 bedroom apartment in Maho Village

Guest favourite

Apartment

4.96 out of 5 average rating, 72 reviews

Discount Offer Ocean & Tropical Garden Views+PERKS

Flat

4.81 out of 5 average rating, 31 reviews

The Rock 2 Duplex Apartment Sea View with Jacuzzi

Guest favourite

Flat

4.96 out of 5 average rating, 96 reviews

Top of the art penthouse

Guest favourite

Flat

5 out of 5 average rating, 10 reviews

Le Colibri - Baie Orientale - Private Jacuzzi

Apartment

4.8 out of 5 average rating, 80 reviews

2 Bed Suite in Condo Hotel, Ocean view, Concierge

Family- and pet-friendly home rentals

Guest favourite

Apartment

4.9 out of 5 average rating, 39 reviews

Orient Bay "B&C Collection" 2BD+Sofa

Guest favourite

Villa

4.99 out of 5 average rating, 81 reviews

Your Paradise Villa

Guest favourite

Apartment

4.83 out of 5 average rating, 93 reviews

Princess Anouk, Orient Bay, swimming pool, on the beach

Guest favourite

Apartment

5 out of 5 average rating, 5 reviews

Luxury apt, direct access to the beach

Apartment

4.71 out of 5 average rating, 31 reviews

Caribbean Dream, Orient Beach. Mont Vernon.

Guest favourite

Villa

5 out of 5 average rating, 26 reviews

Villa Azur, great view of the Orient Bay

Guest favourite

Flat

4.97 out of 5 average rating, 118 reviews

Cupecoy Garden Side

Guest favourite

Villa

5 out of 5 average rating, 24 reviews

Villa tropicale et paella party

Family-friendly home rentals with a pool

Home

4.75 out of 5 average rating, 12 reviews

Nice Villa for 6 Orient Bay Beach

Guest favourite

Home

4.92 out of 5 average rating, 66 reviews

C’est la Vie! Private pool and amazing views !

Apartment

4.8 out of 5 average rating, 15 reviews

Condominium with terrace, pool

Guest favourite

Home

4.88 out of 5 average rating, 52 reviews

Pelican Paradise

Guest favourite

Home

5 out of 5 average rating, 38 reviews

Water access, snorkeling gear & kayaks

Villa

4.91 out of 5 average rating, 32 reviews

Oceanfront Villa with Private Pool

Villa

4.84 out of 5 average rating, 31 reviews

Ocean front "colibris" amazing view

Home

4.78 out of 5 average rating, 37 reviews

Very pleasant ocean view house with swimming pool

Quick stats about holiday rentals that are family-friendly in Simpson Bay

Total rentals
160 properties
Nightly prices starting at
€ 125 before taxes and fees
Total number of reviews
2.1K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
120 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace

Destinations to explore