Vacation rentals with outdoor seating in Simpson Bay

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Top-rated outdoor seating rentals in Simpson Bay

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Guest favorite

Guesthouse in Simpson Bay

4.95 out of 5 average rating, 73 reviews

White Sands Beach Studio

This is the studio apartment you want. In a prime location in a safe neighborhood, with everything need to enjoy a perfect vacation. You have supermarkets, car rentals, restaurants, and bars within walking distance. A 30-second walk from Simpson Bay beach &6 min to Maho Beach, our world-famous airport beach. Public transportation is also available there. The apartment is recently renovated and equipped with AC, Netflix, a cozy kitchen, a magnificent garden, and a terrace overlooking the airport.

Guest favorite

Rental unit in Simpson Bay

5 out of 5 average rating, 5 reviews

*NEW* Modern Boho-Steps to the Beach & Has It All!

An oceanfront gem in Beacon Hill, on Simpson Bay Beach with steps down to one of SXM’s best beaches. Totally redone in 2024, it features two king bedrooms, a state of the art kitchen, new zen bathrooms, chic modern boho decor, and all-new furnishings. Enjoy the outdoor patio or the rooftop deck with 360-degree views, big-screen TVs, high-speed WiFi, and a fully stocked kitchen. Located in a safe, gated community with designated parking, close to amenities, it's Beacon Hill's most beautiful unit.

Guest favorite

Rental unit in Simpson Bay

5 out of 5 average rating, 17 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.

Superhost

Rental unit in Simpson Bay

4.86 out of 5 average rating, 193 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.

Superhost

Rental unit in Simpson Bay

4.85 out of 5 average rating, 13 reviews

At the Beach: Beachfront Oasis

Dive into St. Maarten's charm from our chic 1st-floor beachfront apartment. Direct ocean views await from the porch in a secure gated community. Features Modern amenities include Full Size Sleeper Sofa, AC, smart TV, WiFi, full kitchen, & washer/dryer. Located just 15 mins to the airport, near the Causeway, and close to casinos & eateries. Enjoy our private pool, direct beach access, free private parking & nightly security. Discover the perfect blend of location & beachfront luxury.

Guest favorite

Condo in Lowlands

4.95 out of 5 average rating, 106 reviews

Sint Maarten La Terrasse Maho

It's a cozy large studio with a king size bed, a queen size sleeper sofa and a big balcony, it is at the second floor at Royal Islander Club Resort La Terrasse in Maho, fully equipped and furnished. Located just in front of Maho Bay beach and few minutes walk from Mullet bay beach. There are few restaurants and boutiques like cigar shops, jewelers and beauty store. Casino Royale is right next door. There are also a supermarket for grocery shopping, a pharmacy, a clinic and more...

Guest favorite

Rental unit in Simpson Bay

5 out of 5 average rating, 191 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

4.89 out of 5 average rating, 187 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!

Guest favorite

Rental unit in Simpson Bay

4.97 out of 5 average rating, 178 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. New totally refurbished modern apartment with modern amenities and comforts. A perfect vacation spot !

Guest favorite

Villa in Cul-de-Sac

4.95 out of 5 average rating, 100 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"......

Guest favorite

Rental unit in Simpson Bay

4.99 out of 5 average rating, 69 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.

Guest favorite

Rental unit in Simpson Bay

5 out of 5 average rating, 113 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. 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.