Vacation rentals in Red Pond Bay

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Top-rated vacation rentals in Red Pond Bay

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Guest favorite

A modern villa is depicted in a gated community, featuring a multi-level structure with large windows. An infinity pool is surrounded by several lounge chairs, and a patio area with dining furniture is visible. Lush greenery enhances the outdoor space.

Home in Upper Prince's Quarter

5 out of 5 average rating, 8 reviews

Ocean Pearl - Spacious Villa in Dawn Beach

Welcome to our stunning & modern villa in the gated community of Dawn Beach! This spacious retreat offers 6 large, comfy bedrooms (4-bedroom option available), with gorgeous bathrooms. Relax in the huge open plan living/dining area and updated kitchen. Step out to the expansive patio with an infinity pool and breathtaking views of both the Dutch and French sides. Plus, a backup generator ensures your stay is hassle-free. 2-car garage and extra parking included. Perfect for your island getaway!

Guest favorite

An outdoor lounge area features a modern pergola with plush seating and neatly arranged towels. The infinity pool, with its seamless edge, reflects the vibrant blue of the ocean under a clear sky, providing expansive views of the coastline and surrounding landscape.

Home in Upper Prince's Quarter

4.96 out of 5 average rating, 53 reviews

Teresa’s Ocean Paradise

St. Maarten’s best kept secret with breathtaking ocean views from every room! Step into Teresa’s Ocean Paradise where you’ll wake up to panoramic views of turquoise water. Nestled in a private gated community with a communal pool overlooking the ocean, fully equipped kitchen, and two king bedrooms – each with private bathrooms. Perfectly located to enjoy the best of the Dutch and French side’s beaches and restaurants. A one-of-a-kind property to make your vacation an unforgettable retreat.

Guest favorite

A crystal-clear swimming pool is set against a backdrop of the Caribbean Sea and distant hills. Blue lounge chairs are positioned along the pool deck, inviting relaxation. The vibrant blue sky above complements the serene landscape, enhancing the tranquil environment of the villa.

Home in Upper Prince's Quarter

4.97 out of 5 average rating, 71 reviews

Villa Tamarind | Luxury Oasis | Ocean views | 4BDR

Villa Tamarind is a unique luxury rental property. It truly is our home away from home and outfitted with fun and comfort in mind. We are located on the Dutch side, minutes from the French border, in a quiet gated community with the best views of the whole island. This is the perfect place to build memories with friends & family while you listen to the soothing sound of the waves, relax in the property's pool surrounded by swaying palms, and enjoy the villa's fantastic cooking equipment.

Guest favorite

An open-plan living area features large windows providing views of the ocean. A comfortable sectional sofa is positioned alongside a textured area rug with floral patterns. A dining table for six is nearby, and a wooden TV console holds a flat-screen television.

Apartment in Upper Prince's Quarter

4.94 out of 5 average rating, 18 reviews

Guana Bay Beach Condo

It's all about the views at the Guana Bay Beach Condo! With a wrap around balcony on the second floor, you are sure to enjoy the sunrises and views of St. Bart's and the Atlantic Ocean. Just a 2 minute walk to a very private spectacular beach. The condo is very comfortable with one bedroom, one and a half bathrooms, fully stocked kitchen. It also includes AC and a washer/dryer for your convenience and a fully stocked kitchen. Downtown Philipsburg is just a 5 minute drive away.

Top guest favorite

A modern kitchen and living area are visible, featuring a large island with bar seating, complemented by pendant lighting. Floor-to-ceiling glass doors provide access to an outdoor terrace with ocean views. Natural light fills the space, enhancing the contemporary decor.

Home in Upper Prince's Quarter

5 out of 5 average rating, 19 reviews

Aman Oceanview

The Aman Oceanview is an oasis of calm, luxury and elegance, built into the hillside overlooking the sublime and sparkling Atlantic Ocean and Saint Barth. This a brand new modern property consists of two master bedrooms with two bathrooms, living room with fully equipped kitchen, exterior terrace and laundry area. All two bedrooms, the living room have unobstructed views of the ocean. A breathtaking infinity pool and a sundeck overlook the ocean, form the focal point of Aman

Superhost

A spacious studio apartment features a comfortable bed with decorative pillows and a large wall art piece depicting an elephant. A sleek coffee table is positioned in front of a plush sofa, while natural light enters through large windows adorned with patterned curtains.

Apartment in Oyster Pond

4.87 out of 5 average rating, 135 reviews

Lovely Studio Apartment with Pool & Nature Views!

Take a break and unwind at this peaceful studio apartment, perfect for your Caribbean getaway! This fully equipped studio is located just 7-10 minutes away from the capital, Philipsburg, and a few minutes away from several beautiful beaches. It also has gorgeous scenic views and an inviting and relaxing pool! As well as a rooftop terrace with scenic 360 views. Baby crib and grill available upon request for small fee and washer & dryer available on premise for free use.

Guest favorite

An inviting outdoor terrace showcases a comfortable seating area with black wicker furniture, set against the backdrop of a sparkling infinity pool. The ocean horizon stretches beyond, while lush greenery and bright skies add to the serene atmosphere.

Villa in Upper Prince's Quarter

5 out of 5 average rating, 8 reviews

Luxe 3BR Villa: Pool & Sweeping Ocean Views

Discover Villa Kyash, an architectural gem where your private infinity pool dissolves into the endless horizon. This flawlessly designed 3-bedroom, 3-bathroom sanctuary in tranquil Dawn Beach perfects the art of indoor-outdoor living. Sun-drenched terraces with a gourmet grill give way to a serene, air-conditioned interior where three king bedrooms ensure ultimate privacy. Curated for discerning families or groups, this is where luxury and tranquility become your reality.

Guest favorite

A private balcony features a small table and two wooden chairs, offering an unobstructed view of the ocean and the horizon. The sea breeze can be felt from this elevated space, framed by white balustrades that enhance the serene outdoor setting.

Apartment in Upper Prince's Quarter

4.91 out of 5 average rating, 86 reviews

702 w/ a view at Princess Heights

Forget your worries in this spacious and serene luxurious condo on the top floor . Wake up to the breathtaking view of the blue ocean with St. Barts on the horizon. 702 offers the best amenities with relaxation in mind. Lounge on the balcony, BBQ in the courtyard or take a stroll on the beach, there is no wrong way to experience this condo on the beautiful and friendly island of St. Maarten. NO WORRIES ...THERE IS A GENERATOR ON PREMISES IN CASE OF POWER OUTAGES

Guest favorite

An aerial view of the villa showcases its modern architecture with a terracotta-tiled roof and expansive outdoor spaces. A large infinity pool reflects the surroundings, while shaded areas with loungers and a fire pit area provide spaces for relaxation and gathering.

Villa in Upper Prince's Quarter

4.94 out of 5 average rating, 109 reviews

The Blue Door Villa - 4 bed ocean view home

At the Blue Door Villa, we offer our guests all the creature comforts of being in a well-equipped vacation home. We are located on the Dutch side, minutes from the French border in a quiet gated community. The Blue Door Villa is a perfect place to relax while you listen to ocean waves and swim in the infinity pool. There are multiple outdoor spaces offering privacy or space to gather. We are now offering our guests an exclusive, free concierge service.

Superhost

A serene infinity pool is viewed from the terrace, merging seamlessly with the ocean horizon. Two glasses of orange juice rest on a dark table, reflecting the inviting blue hues of the water and the expansive ocean in the background.

Home in Upper Prince's Quarter

4.89 out of 5 average rating, 18 reviews

Ocean view villa at Dawn beach

Enjoy stunning ocean view in a peaceful location free of traffic and crowds. Villa Seascapes is a fully renovated luxury villa with a 180 degree unobstructed ocean view, surrounded by a lush garden. 3 beautiful bedrooms 8 min walk to Dawn beach, bar and restaurant. Salt water infinity pool. Large terrace overlooking the ocean. Each bedroom has en suite bathroom, walk in closet and magnificent ocean view.

Top guest favorite

A serene cocktail pool is positioned on a deck, surrounded by lush greenery. The clear water reflects the blue sky and ocean view, with distant waves gently crashing on the shore. Natural elements evoke a feeling of tranquility and connection to the environment.

Villa in Upper Prince's Quarter

5 out of 5 average rating, 18 reviews

Modern house, cocktail pool, ocean view

Stay at a beautiful duplex home in Oyster Pond. With a cocktail pool, a breathtaking ocean view and a modern interior design, this spacious and fully equipped home is ideal for a couple. Enjoy the peace of the neighborhood and also benefit from a 24/7 gated security. This home will offer everything you need for an amazing stay in Sint Maarten / Saint Martin.

Guest favorite

An aerial view of a modern apartment nestled within a lush garden. The building features a sleek design with a solar panel roof. Outdoor seating is visible on the balcony, surrounded by greenery. A parking area accommodates a vehicle, and a BBQ space is present in the garden.

Apartment in Upper Prince's Quarter

4.96 out of 5 average rating, 72 reviews

Apartment in tranquil, gated community.

This is a quiet and comfortable appartement with private parking and entrance. It sits in a large garden including a BBQ place. It is a modern appartement and the location is inside a gated community. It is underneath our own living space, so we are nearby for questions and extra assistance. The bed is the equivalent size of Californian King.