Condo holiday rentals in Simpson Bay

A serene pool area is surrounded by neatly trimmed grass and tropical plants. Several lounge chairs are positioned around the water, offering relaxation space. Shade is provided by umbrellas, while a view of distant buildings and a waterway is visible in the background under soft evening light.

4.9 out of 5 average rating, 102 reviews

Havya Cozy Stays | In Maho, Near Beaches & Airport

Keep it simple at this peaceful, well located studio unit at The Emerald at Maho with a common pool and gym. Just 5 minutes away from the International Airport, and walking distance from beaches with one being St. Maarten's famous end of the runway beach. Nowhere else in the world are you able to witness take-off and landing of Jumbo-jets as closely as here, all while sipping on a cocktail. Many shops stay open until 11pm, many bars, restaurants, nightclubs are all within easy walking distance.

A cozy living area features a comfortable gray sofa and a wooden coffee table. Two windows offer expansive views of the ocean, with light reflecting off the water. Beams stretch across the ceiling, enhancing the airy feel of the space.

4.81 out of 5 average rating, 182 reviews

Oceanfront w Pool | Maho Beach area

Location , Location Location ! You can not get any closer to the ocean than in this cliff side apartment. The sound of waves crashing below and incredible ocean views from every room. The sunrise is magical everyday and by night the glowing lights of Simpson bay. This cliff side apartment has everything you need for a dream stay away from the crowds. . Just steps from 4 beaches Simpson bay, Mullet bay, burgeux bay and a 5minute walk to the world famous Maho Beach with its famous plane landings

5 out of 5 average rating, 17 reviews

Condo in Indigo Bay

Luxury Condo "The Q" + Huge Pool Patio + Beach/Bar

This luxury 2-bedroom, 2-bathroom apartment boasts breathtaking ocean views and a private expansive pool, offering a sense of serenity that’s unmatched. Largest pool in the neighborhood. Ocean views from shower! Thoughtfully managed by a top-tier host, every detail has been considered to ensure your stay is comfortable and unforgettable. Nestled near the beach and steps away from a chic beach bar, this place provides some of the island’s best views—an oasis of beauty in the heart of St Maarten.

4.88 out of 5 average rating, 52 reviews

Condo in Sint Maarten

Apt5 (2 bedrooms, terrace & sea view)

Spacious and breezy Duplex with 2 bedrooms and big a terrace with sea view. Located in Black Palm, an elegant residence of 6 apartments in Indigo Bay, a calm and exclusive neighborhood. Indigo Beach is just a 5-minute walk away. Enjoy the shared pool with sea view. Ideal for up to 4 guests: couples, families or friends looking for relaxation. -5 minutes’ walk from Indigo Beach -5 minutes’ drive from the nearest supermarket -Private parking on site -Concierge service available for any request.

A serene view of the property’s swimming pool surrounded by lush greenery and palm trees. Loungers are positioned along the poolside, providing spaces for relaxation. The turquoise waters of Simpson Bay are visible in the background, complemented by a clear blue sky.

4.89 out of 5 average rating, 62 reviews

Beachfront Paradise with Pool & Stunning Sunsets

Escape to a beachfront paradise with a pool and stunning sunsets. Wake up to the soothing sound of ocean waves and lounge on the private patio overlooking turquoise waters. Step onto white sandy beaches with direct access, or stroll to nearby restaurants and vibrant nightlife. Your coastal sanctuary offers unforgettable moments of relaxation and tranquility. Designed for comfort and convenience, the community and unit include: • Ocean-view pool • Elevator access • Full-building generator

4.97 out of 5 average rating, 103 reviews

Condo in Marigot

cosy apartment

Profitez d'un logement élégant et central. Proche de la capital (Marigot) avec des commerces et des restaurants a 10 minutes a pied, un accès piscine et plage privé, le marche de marigot est proche avec son poisson Frais tout les mercredi et samedi matin. Nous attirons l’attention des voyageurs sur le fait que les conditions météo propres aux antilles peuvent amener des coupures temporaires de la distribution de l’électricité et de l’eau. Nous précisons que ces désagréments son peu fréquents

A spacious bedroom features a large bed adorned with white linens and a soft gray throw. Three framed black-and-white prints are displayed on the wall above the bed, while a window offers views of the beach and ocean beyond.

4.92 out of 5 average rating, 134 reviews

Modern Oceanview 2-Bedroom Condo on Mullet Bay

Welcome to Fourteen, one of the most luxurious beachfront residences in St Maarten located directly on the famous Mullet Bay beach and golf course. Located on the 9th floor, You will find this spacious 2 bedroom condo offering beautiful ocean views, great for a group, family, or romantic getaway. Indulge yourself in all of the amenities, outstanding concierge services and dining experience Fourteen has to offer. We aim to make your stay unforgettable. $5 per night resort fee not included

A modern sleeping area features a queen bed with a light-colored quilt and decorative pillows. Shelves above the bed display decorative items. Floor-to-ceiling sliding doors lead to a balcony. Wooden flooring complements the light walls, and a small area rug adds warmth.

4.84 out of 5 average rating, 86 reviews

Maho studio overlooking airport, Free Wi-Fi!

Welcome to "Flight Deck", a cozy and unique studio apartment overlooking the Princess Juliana International Airport & runway and beautiful Simpson Bay Beach. This unit is in a prime location, as it is just a 5 minute walk to the heart of Maho Village, which is full of shops, restaurants, bars, nightclubs, casinos, and the world famous Maho Beach, where thrill-seekers can stand just feet below planes as they land and experience the thrilling sensation of the jet blast of planes taking off.

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.

5 out of 5 average rating, 44 reviews

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub

A spacious apt in a great location. This apt is located on the 2nd and 3rd floor in a gated +24/7 secured community of the Simpson Bay Yacht Club. A fully stocked kitchen. Open concept Dining/Living room combination leads to a covered patio for outdoor dining with panoramic bay views. 2 large and spacious bedrooms with private baths. Enjoy morning coffee or afternoon cocktails on one of the 3 patios all overlooking water. This complex offers 2 pools, Tennis, Jacuzzi, security and parking.

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.

4.88 out of 5 average rating, 17 reviews

Sur Mer - Beachfront 3 bedroom on Simpson Bay

✨Sur Mer with IRE Vacations ✨ Directly on the beach of Simpson Bay, this spacious 3 bedroom, 3 bathroom apartment is the perfect place for your next Sint Maarten vacation. In a private residence Sur Mer is close to the airport, restaurants, shops and night life. Step out onto the white sandy beach, or catch the sunset on your balcony while listening to the crashing waves below. You can admire planes taking off and landing from your back terrace. Shared pool and gym within the residence.

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.

4.95 out of 5 average rating, 125 reviews

Saint 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...

4.98 out of 5 average rating, 51 reviews

A spacious terrace is visible, featuring two sun loungers positioned for a view of the sea and surrounding hills. The railing offers an unobstructed sightline of the coastline and lush greenery under a clear blue sky.

Condo in Cul de Sac

Koala 1 – Elegant 1 Bedroom Duplex Sea View

Welcome to Koala – a stylish apartment with sea views located in a small residence with pool, in the heart of the secure estate of Anse Marcel. It offers several advantages for a relaxing holiday: * Access to the residence's swimming pool * Master bedroom with king size bed * Full air conditioning * A spacious terrace equipped with an outdoor living room with sea view, * Fully stoked and equipped kitchen * Laundry area (washing machine, etc.) * 2 beach chairs available * Cistern

Popular amenities for Simpson Bay condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

Condo in Collectivity of Saint Martin

A covered terrace features a dining area with a table set for meals. Beyond, a private garden is visible, bordered by stone and lined with various plants, leading to a view of the sea. Two loungers are positioned for relaxation.

4.97 out of 5 average rating, 71 reviews

Feet in the ocean, Orient Bay, Beach apartment

4.87 out of 5 average rating, 31 reviews

A vibrant view showcases the turquoise sea and white sandy beach from a balcony. A spacious outdoor table with two chairs is visible. Inside, a cozy sleeping area is presented with warm tones and large windows, allowing natural light to illuminate the space.

Condo in Cul-de-Sac

Guest Favorite on the beach Sublime sea view. Pool

5 out of 5 average rating, 9 reviews

Condo in Baie Orientale

NEW! Orient Bay's best view 2 bedrooms 2 bathrooms

A well-maintained outdoor pool is surrounded by lounge chairs, offering a relaxing space for guests. Shade is provided by large umbrellas, and tropical palm trees are visible in the background. The pool area is complemented by modern residential buildings, enhancing the serene environment.

4.98 out of 5 average rating, 94 reviews

Brand New- Maho Condo Studio with Seaview and Pool

4.97 out of 5 average rating, 32 reviews

The living area features modern furnishings, including a light sofa, a coffee table, and two armchairs. A dining area with a wooden table is visible, along with large sliding doors that reveal an ocean view and a spacious balcony. Natural light floods the space.

Condo in Sint Maarten

Casa Nova, Indigo Bay SXM

A white, modern condo complex is set atop a rocky outcrop overlooking a sandy beach. Waves gently lapping at the shore and a clear blue sky serve as a backdrop, creating a serene coastal atmosphere.

4.94 out of 5 average rating, 71 reviews

Coral Villa- Steps From BEACH!

4.98 out of 5 average rating, 50 reviews

A cozy living area features a plush sofa with decorative cushions, providing a warm welcome. Large glass doors open to a terrace with a view of the lush garden and lagoon. The indoor dining set is positioned nearby, basking in natural light.

Condo in Marigot

Sunset Lodge: Sunny Cozy, Lagoon View & Good Deals

5 out of 5 average rating, 9 reviews

A spiral staircase made of wood and metal leads from a cliff down to a sandy beach. The surrounding area features lush greenery and rocky outcrops against a backdrop of clear turquoise water. The sky is bright with a few scattered clouds.

Condo in SX

Cliffhanger I-1Br

Pet-friendly condo rentals

Condo in ORIENT BAY-SAINT MARTIN

A wooden pathway leads to two swimming pools, surrounded by neatly arranged palm trees. The clear blue sky creates a bright atmosphere, while the smooth, tiled surface provides a seamless connection to the pool area.

4.82 out of 5 average rating, 57 reviews

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

4.86 out of 5 average rating, 152 reviews

A view of a sandy beach with crystal-clear turquoise waters. Gentle waves are visible lapping at the shore. A few boats can be seen in the distance against a backdrop of a bright blue sky dotted with fluffy clouds. Lush green foliage frames the scene.

Condo in Saint Martin

2 Bedroom Duplex up to 5 guests right on the beach

5 out of 5 average rating, 23 reviews

Condo in Anse Marcel

Rare gem, breathtaking sea views

Condo in Collectivité de Saint-Martin

An outdoor pool glistens under clear skies, surrounded by tropical landscaping. A view of rolling hills and the coastline is visible in the distance, showcasing blue waters and sandy beaches. Lounge chairs are placed along the pool's edge, creating an inviting relaxation area.

4.65 out of 5 average rating, 20 reviews

Duplex Frangipanier with sea view and Saint Barth

A modern living area features a sleek black cabinet and a comfortable armchair. Natural light floods through a sliding glass door, revealing a balcony with a small table and chairs. Lush green palm leaves are visible through the glass, enhancing the serene atmosphere.

4.81 out of 5 average rating, 47 reviews

Bright studio next to the beach

A light-filled living area features a spacious sofa adorned with neutral-toned pillows, complemented by a small wooden table and a variety of seating. Large windows invite natural light, while a modern kitchen area, equipped with sleek appliances, promotes an open atmosphere with views of palm trees outside.

4.95 out of 5 average rating, 21 reviews

Beautiful Large 2 Bedrooms apartment in Maho

A spacious apartment complex is set amidst lush greenery, showcasing a modern design with multiple balconies in varied shades of orange and white. The building appears well-maintained and integrates harmoniously with the surrounding landscape.

4.94 out of 5 average rating, 34 reviews

Island 517 Cupecoy St. Maarten

Condo in Collectivité de Saint-Martin

An open-concept living area is highlighted by large glass doors, providing an unobstructed view of the pool and garden. A dining table is set with modern chairs, while a comfortable sofa sits in the corner. Kitchen appliances are neatly arranged in sleek cabinetry.

4.77 out of 5 average rating, 22 reviews

Blue vista - Paradise in nettle Bay-1BR Queen Size

Condo rentals with a pool

Condo in Collectivity of Saint Martin

A spacious terrace offers direct views of sandy beach and gentle waves. Two lounge chairs are positioned for relaxation under a shade. The background features a rocky shoreline and lush mountains, while a clear sky enhances the inviting coastal scenery.

5 out of 5 average rating, 39 reviews

Waterfront, beautiful ELBA! 2 to 4 people

An inviting infinity pool is positioned adjacent to the shoreline, offering unobstructed views of the Caribbean Sea. Lush palm trees frame the scene, while the sun reflects off the water's surface, creating a serene atmosphere. The surrounding terrace features natural stone tiles.

5 out of 5 average rating, 51 reviews

The Cliff in Cupecoy Beach HEAVEN!!!

4.96 out of 5 average rating, 51 reviews

A wooden dining table is set for two, featuring a bowl and plates. The view overlooks a coastline with a sandy beach and rolling hills under a clear blue sky, with houses and greenery visible in the distance.

Condo in Orient Bay

Studio Iguana

4.86 out of 5 average rating, 14 reviews

A poolside area features a sunshade structure providing partial cover over lounge chairs. A small, clear pool is visible beside a wooden deck adorned with potted plants, while views of lush hills and the distant ocean enhance the tranquil setting.

Condo in Little Bay

Little Bay Condo with Private Pool

5 out of 5 average rating, 4 reviews

Condo in Indigo Bay

2 Master Suites, Private Pool, & Walk to Beach

A large private pool is framed by vibrant greenery and colorful flowers. Sun loungers line the pool area, and a cruise ship is visible in the distance along the ocean, with the picturesque shoreline beyond.

4.9 out of 5 average rating, 50 reviews

Maho 1 Bed Condo with ocean view & Free Wi-Fi

4.97 out of 5 average rating, 35 reviews

A refreshing private pool is framed by a wooden deck, featuring vibrant red umbrellas for shade. Surrounding tropical plants add greenery, while a stunning ocean view is visible in the background under a clear blue sky.

Condo in Cupecoy

Porto Cupecoy 4-Bedroom Penthouse

A spacious living area is illuminated by natural light from large glass doors, revealing stunning water views. Modern furniture includes a large sectional sofa with decorative pillows, a coffee table, and a dining space with contemporary chairs. Light tile flooring contributes to the airy ambiance.