Vacation rentals in Simpson Bay

4.8 out of 5 average rating, 166 reviews

Condo in Simpson Bay

Oceanfront w private 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, 26 reviews

Home in Sint Maarten

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

Welcome to paradise in Indigo Bay, St. Maarten! Our brand new property offers ultimate indoor-outdoor living with sliders opening to breathtaking sea views. Open-concept layout, fully-equipped kitchen, private pool and courtyard, NO STEPS, and three ocean-view bedrooms. Experience luxury and comfort at our oceanfront villa. Book now for an unforgettable vacation! *There is construction of a new hotel in the bay. Noise has been minimal but is subject to change. Contact us with any questions!*

4.88 out of 5 average rating, 8 reviews

An outdoor terrace is presented with white loungers and a table, overlooking the sandy beach and turquoise water. Sailboats can be seen in the distance against a clear blue sky. The setting offers a tranquil and relaxing atmosphere near the sea.

Home in Marigot

Sweet Home on the Beach.

SITUATION Exceptionnelle. Vue sur la baie de Marigot Pieds dans l’eau Face à la Mer des Caraïbes Superbe plage de sable blanc, cocotiers, mer turquoise ATOUTS Maison duplex sur la plage Situation idéale pour visiter 4 Piscines 1 tennis Un beau jardin Résidence sécurisée 24H/24H Parking gratuit A côté : supermarché, boulangerie, restaurants Idéal pour Couple Famille ou Amis BON A SAVOIR A 2 kms de Marigot Voiture location conseillée Wifi, forfait ménage, serviettes, draps inclus dans le prix.

Condo in Collectivity of Saint Martin

Two lounge chairs are positioned on soft sand, accompanied by rolled beach towels. Lush greenery and palm trees frame the scene, while a covered outdoor seating area is visible in the background, offering a glimpse of a relaxed beachfront atmosphere.

5 out of 5 average rating, 14 reviews

Bora Bora, on the beach, sea view 2 to 4 people

You dreaming of a vacation on the beach, you will not be disappointed. This apartment with direct sea view for 2 to 4 people is located in a quiet, secure and private residence, 4 swimming pools, tennis courts, parking lots. This little gem is fully equipped. At sunrise you will have your meals on a large terrace surrounded by palm trees, your feet in the sand admiring the beauty of the immense garden and in the evening before sleeping, the lights of the Island of Anguilla will transport you

5 out of 5 average rating, 26 reviews

A shimmering pool sparkles in the foreground, surrounded by lounge chairs. In the background, the tranquil turquoise waves meet the shoreline, with sailboats gently bobbing on the water. Lush palm trees frame the scene, creating a serene coastal atmosphere.

Condo in Simpson Bay

Beachfront Caribbean Breeze in Paradise, SXM

Caribbean Breeze inviting Beach front home. A few steps to our beach and pool. Walk to main stream. Amazing views . 2/2.5 with huge Master. Hear the waves flowing in onto the shore for those relaxing days and nights. New kitchen, living room , bathrooms, dinning area,etc. An Caribbean feel. Unwind on any balcony, penthouse ocean view, on daybed with a nice drink , looking over the verse tranquil ocean. Take a dip in the soothing crystal clear waters. Amenities enclosed & Wi-Fi included.

5 out of 5 average rating, 9 reviews

Home in Little Bay

5B Oceanview villa near Philipsburg

Hilltop Villa w/ Stunning Ocean & Pond Views Near Philipsburg Welcome to your dream getaway in St. Maarten/St. Martin! Perched atop a picturesque hill, this villa offers nearly 3,000 square feet of interior space, a 1,200 square foot sun deck, and an infinity pool. Enjoy breathtaking views of the ocean, pond, and lush hillsides. With over 500 square feet of balcony and terrace outdoor space, this spacious retreat is ideal for families or friends seeking a peaceful, luxurious island escape.

Apartment in Collectivity of Saint Martin

4.91 out of 5 average rating, 11 reviews

Just in paradise with lagoon's view

Situé au 2ème étage dans une résidence au bord du lagon sur la baie Nettlé . Joliment décoré, tout confort, entièrement équipée et climatisé, avec une superbe vue. D'une surface de 50m2, idéal pour une ou deux personnes (deux à deux places) , cet appartement peut accueilr jusqu'à 7 personnes (lit bébé et lits singles supplémentaires fournis sur demande) Coin salon Espace bureau salle à manger sur la terrasse Salle de bain avec baignoire Deux piscines. Un coucher du soleil inoubliable !

Apartment in Upper Prince's Quarter

A panoramic view of the Caribbean Sea is captured, featuring varying shades of blue water meeting the horizon. Lush greenery in the foreground complements the coastline, with the rocky terrain visible beyond the tranquil waters.

4.76 out of 5 average rating, 17 reviews

The Tree House SXM

Want to life a sunny vacation in the beautiful Caribbean Island of St. Maarten, 15 minutes near the beaches and the center of Philipsburg. With unrivaled point-blank views of the Caribbean Sea, set within a meticulously renovated old villa in a quiet residential area, this fully furnished one bedroom apartment is a rare gem. Including Wi-Fi, A/C and the bedroom is appointed with a built-in closet. Best of all is the outside porch with stunning ocean views and a unique cruise ships vista.

Home in Les Terres Basses

An aerial view of the villa showcases a private pool surrounded by a spacious terrace. Lounge chairs and a hammock are visible, with glass railings enhancing the open feel. The lush greenery and distant mountains provide a scenic backdrop under a clear blue sky.

5 out of 5 average rating, 6 reviews

Villa Ellia - Modern luxury in St Martin FWI

Located in the prestigious Lowlands, this villa is your dream vacation spot with its breath-takings views on our beautiful green mountains. The villa is 5 minutes away from beaches, supermarkets, gyms, and activities. We will take great pleasure in hosting you. When renting with us you get concierge services to facilitate all things during your stay. Villa Ellia has 4 bedrooms and 4 bathrooms, the master bedroom and the kitchen have direct access to the large terrace and the private pool.

Apartment in Cupecoy Beach

A bright living area is presented with large floor-to-ceiling windows offering panoramic views of the Caribbean landscape. A comfortable beige sofa is paired with two wooden tables on a patterned rug. Lush greenery enhances the inviting atmosphere.

5 out of 5 average rating, 5 reviews

Exquisite 2 Bed Luxury Apt w Views Walk to Beach

Make your escape a luxury experience in paradise at this unique and tranquil getaway. Prepare to de-stress and to be mesmerized by the continuous influence of the sunlight and the sea. Enjoy panoramic turquoise views and a Caribbean Sea breeze that will bring you complete comfort. This coastal sanctuary beckons with unforgettable moments of tranquility. Professionally designed and managed to make sure that no detail was over looked. Rated one of the best says in Saint Maarten!

4.92 out of 5 average rating, 83 reviews

A patio area features a round glass table surrounded by two comfortable chairs, offering a view of the lush green landscape and distant water. The bright yellow railing complements the open space, creating an inviting spot for relaxation amidst the natural surroundings.

Apartment in West end

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. we also have scooters for rent $30per day. we can take you to the beaches and pick you up $30

4.66 out of 5 average rating, 64 reviews

A private pool extends seamlessly into the view of the beach and ocean. Comfortable seating is arranged on the terrace, complemented by a vibrant green plant. The distant mountains and fluffy clouds form a picturesque backdrop against the bright blue sky.

Condo in Pelican

SeaLaVie Apartment with Private Pool

Welcome to the stunning St. Maarten Beachfront Apartment with Private Pool! This luxurious Airbnb property offers an unforgettable vacation experience in one of the most beautiful and sought-after destinations in the Caribbean. Perched on the pristine white sands of St. Maarten's exquisite Kimsha beach, this beachfront apartment boasts breathtaking panoramic views of the turquoise waters and the endless horizon.

Vacation rentals for every style

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Popular amenities for Simpson Bay vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Simpson Bay's top sights

Maho Beach72 locals recommend

Carrefour Market, Sint Maarten61 locals recommend

Karakter Beach Bar/Restaurant48 locals recommend

Avantika36 locals recommend

Soggy Dollar Bar31 locals recommend

The RedPiano Lounge29 locals recommend

Simpson Bay oceanfront vacation rentals

5 out of 5 average rating, 5 reviews

A well-lit bedroom features a spacious bed adorned with a colorful patterned quilt. Large glass doors open to a balcony, offering views of the surrounding area. Light-colored walls and stylish furniture contribute to the room's contemporary look.

Apartment in Lowlands

Modern Cozy Stay Steps From Mullet Beach

5 out of 5 average rating, 42 reviews

A bright living area features a comfortable sofa and a wooden coffee table, with natural light flowing in through large sliding doors. The space is complemented by woven light fixtures and a decorative wall hanging, offering views of the outdoor seating and lush surroundings.

Home in Cul-de-Sac

Water access, snorkeling gear & kayaks

4.96 out of 5 average rating, 193 reviews

A dining area features a modern table with four chairs, positioned near large windows showcasing panoramic views of the turquoise sea and sandy beach. A wall mirror reflects the inviting atmosphere, while lush greenery can be seen outside, enhancing the coastal ambiance.

Apartment in Simpson Bay

Lilly's Beach

5 out of 5 average rating, 4 reviews

A dining area is set outside, featuring a wooden table with seating for four. Lush greenery surrounds the space, offering a view of the turquoise ocean beyond. The scene highlights the tranquil beach atmosphere, with gentle waves visible in the distance.

Condo in saint martin

RIGHT ON ORIENT BEACH Oceanview Garden Suite 4* 🏝🌞

5 out of 5 average rating, 3 reviews

A terrace is presented with a table set for two, featuring drinks and a tropical view. The ocean sparkles under a clear sky, with soft white sand and palm trees in the foreground, creating an inviting space for relaxation.

Apartment in Simpson Bay

Ocean Edge Blue Water Beach condo. Newly renovated

5 out of 5 average rating, 11 reviews

A covered balcony features a view of a sandy beach and mountainous landscape in the distance. Lush greenery is positioned nearby, and the space is illuminated by natural light filtering through the open area.

Apartment in Philipsburg

Fayalobi - Large 1 bed Beachfront Apt 2nd floor

5 out of 5 average rating, 17 reviews

A refreshing pool area is surrounded by palm trees and colorful tropical plants. Lounge chairs are positioned near the pool, offering views of the turquoise Caribbean Sea and nearby coastline. Natural light illuminates the space, emphasizing the vibrant outdoor environment.

Home in Philipsburg

2 Bedroom Ocean Front Villa, Private Infinity Pool

4.74 out of 5 average rating, 27 reviews

An open living area features a comfortable sofa positioned beside a side table with a lamp. A round dining table with wooden chairs stands on the terrace, offering unobstructed views of the ocean and horizon through large glass sliding doors.

Condo in Étang Chevrise

Top floor, incredible view on ocean and Orient Bay

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Other great vacation rentals in Simpson Bay

5 out of 5 average rating, 18 reviews

Villa in Cul-de-Sac

Villa Pure - 3 BR waterfront with kayaks, wifi, AC

4.67 out of 5 average rating, 12 reviews

A modern kitchen is equipped with sleek cabinetry and contemporary appliances. A white countertop extends into a dining area with three black stools. Large glass doors open to a grassy outdoor space, providing a view of the pool area and distant water.

Home in Sint Maarten

Villa 2 Chambres Indigo Bay

4.88 out of 5 average rating, 8 reviews

The bright living area features a comfortable seating arrangement with white sofas and a wooden coffee table. Large sliding doors open to a view of the outdoors, allowing natural light to fill the space. A dining area is visible in the background.

Townhouse in Cole Bay

Casalinda Amazing Sunsets Pelican Key SXM

Apartment in DUTCH CUL DE SAC

A private pool is situated on a spacious terrace, with sun loungers placed around its edges. The surrounding hills provide a lush green backdrop, while a covered seating area is visible to one side, offering shade and comfort for relaxation.

5 out of 5 average rating, 3 reviews

Tropical Getaway Sxm!

5 out of 5 average rating, 3 reviews

A serene swimming pool with clear blue water is framed by lush greenery. Two turquoise lounge chairs are positioned beside the pool, offering a relaxed spot to enjoy the tranquil view of the Caribbean Sea in the background under a bright blue sky.

Villa in Saint-Martin

Villa vue mer et Piscine Chauffée

4.82 out of 5 average rating, 49 reviews

Colorful bougainvillea flowers frame a stunning ocean view filled with sailboats on the horizon. The bright blue waters and varied shades of the sky highlight the vibrant scenery, creating a serene coastal atmosphere.

Villa in Indigo Bay

Infinity Views Indigo Bay SXM

4.96 out of 5 average rating, 45 reviews

A panoramic view of the southeastern coastline featuring calm turquoise waters and a distant hillside. Boats are anchored in the harbor, with the outlines of the shore and hills providing a tranquil backdrop under an overcast sky.

Villa in Little Bay

Sugarbird Nest: Sunrise Ocean Views | Great Bay