Villa holiday rentals in Upper Prince&#x27;s Quarter

A private pool is bordered by a spacious patio area, featuring two lounge chairs. Expansive ocean views are visible in the background, with lush greenery surrounding the space. A dining table is situated under a covered area, providing a shaded option for meals outdoors.

4.95 out of 5 average rating, 81 reviews

Villa Ocean - Indulge Yourself in Paradise

A three-bedroom, two-bathroom beauty overlooking beach/vast views of the ocean in Indigo Bay. Sunset viewing on the deck, private pool or down to the beach 10 min by walking. 10 min to airport, night life, other popular beaches. Close to town. groceries, restaurants. All the bedrooms have a view of beach and the ocean. There is free wireless internet, TV, air conditioning, a dishwasher, refrigerator, microwave, wine refrigerator, coffee maker, washer dryer, outdoor gas grill and private parking.

LocationFamilyBeach

A two-story villa stands adjacent to a large swimming pool, surrounded by lush greenery and palm trees. The structure features outdoor stairs leading to a spacious deck, with large windows allowing natural light to illuminate the interior. The tranquil setting offers scenic views of the surrounding landscape.

4.82 out of 5 average rating, 90 reviews

Oceanfront Guana Bay Villa with View of St. Barts

This contemporary oceanfront Villa is fully air conditioned and overlooks both Guana Bay & the Atlantic Ocean. Spectacular morning views of the sunrise and panoramic views of St. Barts. Villa Star has been newly renovated in 2025. Luxury 2 BR/2 BA with high tech fixtures. This gorgeous Villa has full cooking facilities, living area, dedicated workspace & wrap-around deck. A 5 minute drive to both Philipsburg and the French side. Tranquil and exclusive neighborhood. This truly is paradise!

ValueLocationDecor

5.0 out of 5 average rating, 17 reviews

Villa in Philipsburg

Ocean View Villa Little Bay

🌴 Villa Little Bay – Oceanview Bliss With 360° Views Enjoy the peaceful sound of the waves and a serene, private atmosphere that’s still close to everything. We’re located within walking distance to Philipsburg, the vibrant heart of SXM—Front Street, top shopping, restaurants, and the island’s best casinos. The beach is just 5 minutes away, Step outside to your private patio for sunbathing, and shimmering ocean‑view pool. Villa offers the perfect blend of tranquility and convenience.

LocationFamilyComfort

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.

4.9 out of 5 average rating, 21 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.

ValueLocationSleep quality

A private pool is situated on a wooden deck, surrounded by lush greenery and palm trees. Sun loungers are positioned nearby, offering a view of the sea and distant boats. The clear water of the pool reflects the vibrant blue sky.

5.0 out of 5 average rating, 110 reviews

VILLA I LOVE VIEW – Luxury villa with sea view

Villa I LOVE VIEW is an oasis of tranquility – with its private pool (naturism possible), large terrace and luxurious kitchen area. Come and discover its view with multiple shades of blue while relaxing on the deckchairs by the pool with zen natural stone reflections Located in Cul de Sac, facing Saint Barth, Pinel Island and the Eastern Bay. Close to the most beautiful beaches of the island, restaurants, water sports, it is the ideal place for your vacation.

ValueLocationBeach

4.94 out of 5 average rating, 87 reviews

Villa Blue Roc

This luxurious villa is located in a secure residence with a breathtaking view, facing the ocean and the island of St Barthelemy, perched on the heights of Dawn Beach, 15 minutes from the famous beaches/restaurants of Orient Bay and Grand Case in the French part. The villa is also 5 minutes from the Dutch capital, Philipsburg, a must for shopping. Thanks to the large outdoor spaces and the infinity pool, this villa will offer you an unforgettable stay.

LocationFamilyCheck-in

A private pool is framed by wooden decking, complemented by two lounge chairs and a side table. A scenic view of azure waters and distant islands is visible, with sailboats dotting the horizon. Lush palm trees provide a tropical ambiance.

4.85 out of 5 average rating, 156 reviews

Villa Bella sea view pool and jacuzzi 3 bedrooms

Wake up every morning facing Pinel Island, in a modern villa bathed in light, with a private pool and a quiet and green environment. The Villa is located in the Horizon Pinel residence overlooking Îlet Pinel, Petite Clef, Orient Bay, Tintamarre and Saint Barthélemy. It overlooks the incredible and famous Cul de Sac Bay Nature Reserve, known for its population of turtles, rays and pelicans. The shallow and always calm bay is ideal for snorkeling

FamilyLocationOutdoor spaces

An outdoor space features a private pool surrounded by lounge chairs and a dining area with a large table. Palms sway gently in the breeze, framing views of the turquoise waters and lush hills. The deck is paved with light-colored tiles, enhancing the serene atmosphere.

4.96 out of 5 average rating, 137 reviews

VILLA JADE3: 2 BEDROOMS & POOL FEET IN THE WATER

VILLA JADE is a complex of 3 villas, on the waterfront. VILLA JADE 3, our 2 bedroom villa is located in Cul de Sac Bay, facing PINEL Island and the turquoise water nature reserve. Life is peaceful there, kayaking, relaxing, BBQ... You are 5 minutes from the fabulous Baie Orientale, its restaurants, bars and water activities... The 3 villas are adjoining but very private and quiet, your only view is the sea... your only goal is to "enjoy"......

ValueLocationPool

An infinity edge pool reflects the clear blue sky, surrounded by a spacious stone patio. Comfortable lounge chairs are positioned nearby, under an umbrella. The ocean view extends along the horizon, with gentle waves visible in the distance.

4.99 out of 5 average rating, 93 reviews

Sea Haven Villa - Breathtaking Views of Dawn Beach

Sea Haven is a 3 bedroom, 3 1/2 bath villa overlooking Dawn Beach on beautiful St. Maarten. Every room and patio in the villa has an ocean view except the bathrooms. The main floor is an open concept living area with the living room, kitchen, dining area and half bath. There are 3 outdoor patios on the main floor. The large patio off of the living room is furnished with lounge chairs and also leads to the infinity edge pool.

LocationFamilyTV

Villa in Indigo bay, Sint Maarten

A private pool is set in a serene outdoor area, surrounded by lush greenery and palm trees. The pool features a tiled edge, with a wooden tray holding tropical fruits floating in the clear water. A spacious lawn complements the inviting atmosphere.

Ocean Dream Villa

Indulge in luxury at a two-bedroom villa in Indigo Bay, Sint Maarten. Enjoy modern elegance, a private pool, and ocean views. Relax indoors or outdoors, savor gourmet meals, and unwind under starlit skies. Luxurious bedrooms offer ocean vistas. Whether for romance or family, this villa promises a memorable Caribbean escape at Ocean Dream, where luxury meets natural beauty. Book now for an extraordinary island retreat.

FamilyValueCheckout

4.94 out of 5 average rating, 71 reviews

4.99 out of 5 average rating, 104 reviews

A panoramic view captures the serene turquoise waters of Great Bay, framed by rolling hills and lush greenery. The horizon features a blend of clouds and sunlight, creating a tranquil coastal atmosphere. Cruise ships are subtly visible along the shoreline.

Villa in Little Bay

Barefoot Villas GreatBay View in Hot Tub & Balcony

Wake up to stunning panoramic views of Philipsburg and Great Bay. Sip your morning coffee as cruise ships glide into port, all while soaking in the refreshing ocean breeze. This centrally located property puts you just minutes away from Philipsburg’s vibrant shopping scene, local supermarkets, restaurants, and some of the island’s best beaches.

FamilyValueCondition

4.92 out of 5 average rating, 26 reviews

Villa Marant - Elegant Luxury Caribbean Escape

Experience the perfect blend of elegance and comfort at Villa Marant, where modern design meets tranquil relaxation. Nestled in a prime location, our villa offers a stylish retreat for travelers seeking the ultimate escape. Plus, with a backup generator in place, you’ll never have to worry about power outages—your comfort is always ensured.

FamilyValueHeating

Popular amenities for Upper Prince's Quarter villa rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

4.93 out of 5 average rating, 30 reviews

Villa in Oyster Pond

Villa Kyanéa | Ocean View St. Barth · Private Pool

FamilyLocationKitchen

4.81 out of 5 average rating, 16 reviews

AZUR 4BR 4.5BA Walk to Indigo Beach- Sea Side Dr.

LocationHospitalityHeating

An infinity pool is visible in the foreground, its clear water merging with the expansive blue sea. Beyond, the horizon features distant islands under a clear sky, complemented by palm trees swaying gently in the breeze.

4.84 out of 5 average rating, 91 reviews

Villa Indigo Dream, Indigo Bay SXM

LocationValueAmenities

An outdoor dining area is displayed, featuring a white table set with blue glassware. Purple chairs provide seating, while panoramic views of the Caribbean Sea and rolling green hills are visible beyond the patio, showcasing the tranquility of the surrounding landscape.

4.91 out of 5 average rating, 55 reviews

Villa Elysian in Indigo Bay

FamilyValueWalkability

4.75 out of 5 average rating, 12 reviews

An aerial view showcases the villa surrounded by lush greenery and vibrant tropical flowers. The private pool, with a curved shape, is bordered by lounge chairs. The sloped roof of the main house and separate structure add architectural interest.

Villa in Oyster Pond

Palm Paradise - Tropical Villa in Oyster Pond

LocationValueCleanliness

4.95 out of 5 average rating, 19 reviews

Villa in GRAND CASE

Bella Vista - Pool & sea view, 5 minutes from Grand Case

FamilyLocationCleanliness

The villa features a modern design with two levels, surrounded by lush greenery. An infinity pool is situated in front, with reclining chairs positioned nearby. The outdoor dining area is visible, and the expansive glass windows reflect the vibrant surroundings, inviting natural light into the space.

5.0 out of 5 average rating, 34 reviews

Life's Good

ValueFamilyAir conditioning

4.77 out of 5 average rating, 151 reviews

Villa in Lowlands

SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay

LocationFamilySleep quality

Luxury villa rentals

5.0 out of 5 average rating, 16 reviews

Belle Lurette • 3BR waterfront with kayaks, pool

LocationFamilyCheck-in

An open living area reveals wooden beams overhead and large glass doors that connect to the outdoor space. A light-colored sofa rests on polished wood flooring, accompanied by a coffee table. The serene view of greenery and ocean is visible through the doors.

5.0 out of 5 average rating, 49 reviews

Water access, snorkeling gear & kayaks

LocationFamilyLayout

A heated pool is surrounded by a bright tiled patio, featuring two people on colorful chicken floaties. The backdrop offers expansive ocean views under a clear blue sky, with scattered clouds enhancing the tranquil atmosphere.

4.97 out of 5 average rating, 37 reviews

Beach-Private Pool-2 Master King Bedrooms

LocationNearbyOutdoor spaces

4.97 out of 5 average rating, 90 reviews

A stunning sunset is captured over the calm sea, reflecting vibrant colors onto the water's surface. In the foreground, a serene pool mirrors the sky, enhancing the tranquil ambiance of the outdoor space. The silhouette of trees adds a natural element to the scene.

Villa in Simpson Bay

Waterfront "Bonjour" Beacon Hill St Maarten

LocationFamilyQuiet

5.0 out of 5 average rating, 8 reviews

An aerial view showcases the modern villa's sleek white exterior and expansive terraces. Two shimmering pools are highlighted, with stylish loungers arranged for relaxation. The open-plan layout invites outdoor living, seamlessly connecting the indoor and outdoor spaces.

Villa in Grand-Case

Marewa - Breathtaking sea view luxury villa 4hp

LocationFamilyCleanliness

An infinity pool extends toward the horizon, creating a seamless view of Orient Bay and its surrounding islands. Comfortable lounge chairs with orange accents are positioned nearby, offering relaxation against a backdrop of vibrant greenery and a clear blue sky.

4.97 out of 5 average rating, 69 reviews

Private Orient Bay Villa with Spectacular Views

LocationFamilyIndoor spaces

Villa in Les Terres Basses

An infinity pool with crystal-clear water extends alongside the terrace, offering views of the lagoon and surrounding landscape. Palm trees and sun loungers can be seen at the water's edge, with blue skies and fluffy clouds reflecting on the water's surface.

Brand new! - Slowlife - Enjoy Villa

ValueFamilyIndoor spaces

4.98 out of 5 average rating, 46 reviews

4.91 out of 5 average rating, 11 reviews

A private pool is framed by a spacious wooden deck, featuring several lounge chairs and umbrellas for shade. Lush palm trees surround the area, with a clear view of the ocean in the background, complemented by a bright blue sky and gentle clouds.

Villa in Marigot

NEW Les Terres Basses - Villa Coco Paillette - Sxm

FamilyLocationCleanliness

Villa rentals with a pool

4.87 out of 5 average rating, 86 reviews

A modern villa exterior is displayed under a clear blue sky. Sleek white walls are complemented by well-maintained landscaping and palm trees. An outdoor lounge area is visible, featuring comfortable seating and a shaded area for relaxation.

Villa in Simpson Bay

Modern 2 bedroom luxury beachside villa with pool

ValueFamilyAmenities

5.0 out of 5 average rating, 3 reviews

Villa in Orient Bay

NEW Villa Joséphine, a few steps from Orient Beach

FamilyLocationAir conditioning

4.96 out of 5 average rating, 26 reviews

The villa's outdoor area features a private pool surrounded by lounge chairs, complemented by vibrant blue towels. The two-story white structure showcases multiple arched windows and balconies, while lush greenery provides a tranquil backdrop under a clear sky.

Villa in Koolbaai

Caribbean View Villa - Sea - Sunset - Location#1

LocationFamilyBathroom

4.67 out of 5 average rating, 15 reviews

A serene outdoor area features a private pool beside a wooden table and chairs. The view encompasses the ocean and a clear sky, with clouds creating depth. A sunbed is positioned for relaxation near the pool, enhancing the tranquil setting.

Villa in Oyster Pond

Idyllic stay amidst sea, sky, and nature reserve

FamilyLocationCheck-in

Soft cushions in neutral tones are arranged on a stone ledge, overlooking a heart-shaped pool. Lush greenery surrounds the outdoor area, with patio umbrellas providing shade and sunlight filtering through the clouds. A spacious living area is visible in the background.

5.0 out of 5 average rating, 25 reviews

Villa Véronica - Orient Bay

LocationFamilyCleanliness

An outdoor patio area features a dining table set for six and a cozy lounge seating option. A swimming pool reflects the sunlight, while a suspended swing chair adds a relaxing touch. The backdrop showcases a lush, green hillside.

4.99 out of 5 average rating, 87 reviews

Villa Tibo

FamilyLocationOutdoor spaces

Villa in Les Terres Basses

A private pool with turquoise water is surrounded by a spacious wooden deck featuring several lounge chairs. Lush greenery frames the area, and the ocean is visible in the distance under a clear blue sky.

Private villa / beautiful View next to La Samanna

LocationFamilyIndoor spaces

4.88 out of 5 average rating, 24 reviews

An aerial view captures the villa's bright red roofs contrasting with lush greenery. A private pool is surrounded by lounge chairs and palm trees, while the surrounding landscape leads to a pathway. The inviting design harmonizes with the natural environment.