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

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, 91 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!

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5.0 out of 5 average rating, 18 reviews

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.

Villa in Dawn Beach

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!

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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 - villa luxe avec vue mer

Villa I LOVE VIEW est une oasis de tranquillité – avec sa piscine privative (naturisme possible), sa grande terrasse et son espace de cuisine luxueux. Venez découvrir sa vue aux multiples nuances de bleues en vous relaxant sur les transats au bord de la piscine aux reflets pierres naturelles zen Située à Cul de Sac, face à Saint Barth , l'ilet Pinel et la Baie Orientale. A proximité des plus belles plages de l'ile, restaurants, divertissements nautiques, c'est le lieu idéal pour vos vacances.

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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, 157 reviews

Villa Bella vue mer piscine et jacuzzi 3 chambres

Réveillez-vous chaque matin face à l’île Pinel, dans une villa moderne baignée de lumière, avec piscine privée et un environnement calme et verdoyant. La Villa est située dans la residence Horizon Pinel vue sur îlet Pinel, petite Clef, Orient Bay, Tintamarre et Saint Barthélemy. Elle donne vue sur l'incroyable et célèbre réserve naturelle de la baie de Cul de Sac, connue pour sa population de tortues, raies et pélicans. La baie peu profonde et toujours calme est idéale pour le snorkeling

LocationValueHot tub

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 CHAMBRES & PISCINE PIEDS DANS L'EAU

VILLA JADE est un complexe de 3 villas , les pieds dans l'eau. VILLA JADE 3, notre villa 2 chambres est située dans la Baie de Cul de Sac, face à l'Ilet PINEL et la réserve naturelle aux eaux turquoises. La vie y est paisible, sorties kayaks, farniente, BBQ ... Vous êtes à 5 minutes de la fabuleuse Baie Orientale, ses restaurants, bars et activités nautiques... Les 3 villas sont mitoyennes mais très intimes et calmes, votre unique vue est la mer....votre unique but est de " profiter"......

LocationFamilyNearby

5.0 out of 5 average rating, 19 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.

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A private pool is visible in the foreground, surrounded by lounge chairs. In the background, the ocean stretches towards the horizon under a clear blue sky, complemented by lush greenery framing the scene.

5.0 out of 5 average rating, 16 reviews

Beachfront/6 bdrs en-suite/ Maid included (h)

This impressive beachfront luxurious villa, direct private access to the beach, is located in Guana Bay, offering large & spacious living space, with terrace, patio & pool. There are 6 bedrooms, each with en-suite bathrooms. 5 bedrooms with king size beds & 1 bedroom with 2 twin beds. Daily maid service (max 4h) is included. Secure area, quiet place, the villa offers BBQ & games. Ideal for friends & families. COVID Thermometer. 24/7 Maintenance & service. Meeting at car rentals possible.

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4.94 out of 5 average rating, 88 reviews

Villa Blue Roc

Cette villa luxueuse , est situee dans une residence securisee avec une vue epoustouflante , face a l ocean et l ile de St Barthelemy, Perchee sur les hauteurs de Dawn Beach, a 15 minutes des fameuses plages/restaurants d Orient Bay et Grand Case en partie francaise. La villa est egalement a 5 minutes de la capital hollandaise , Philipsburg, un incontournable du shopping. Grace aux grands espaces exterieurs et a la piscine a debordement , cette villa vous offrira un sejour inoubliable.

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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, 94 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.

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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.

ValueFamilyWalkability

4.93 out of 5 average rating, 73 reviews

4.99 out of 5 average rating, 105 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.

ValueLocationIndoor spaces

4.93 out of 5 average rating, 27 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.

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Popular amenities for villa rentals in Upper Prince's Quarter

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

4.83 out of 5 average rating, 18 reviews

Villa in Indigo Bay

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

LocationLaundryHeating

4.94 out of 5 average rating, 32 reviews

Villa in Oyster Pond

Villa Kyanéa | Vue océan St Barth · Piscine privée

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4.95 out of 5 average rating, 81 reviews

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.

Villa in Indigo Bay

Villa Ocean - Indulge Yourself in Paradise

LocationFamilyView

4.85 out of 5 average rating, 33 reviews

A spacious living area is highlighted by large glass doors, allowing natural light to fill the room and offering unobstructed ocean views. Comfortable white sofas complement a wooden coffee table, while vibrant artwork adds a pop of color to the decor. The inviting atmosphere is enhanced by the lush surroundings visible through the windows.

Villa in Sint Maarten

Sea view 3BR Spring Sea Villa w/ pool, St Maarten

LocationValueIndoor spaces

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.

4.81 out of 5 average rating, 94 reviews

Villa Indigo Dream, Indigo Bay SXM

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4.8 out of 5 average rating, 56 reviews

A stunning view features a vibrant infinity pool that blends into the serene landscape. Lush tropical plants surround the area, and a hillside is visible in the background, highlighting the villa's connection to its natural surroundings.

Villa in Cole Bay

SeaSoleil LuxuryVilla With Private Pool IndigoBay

LocationFamilyTV

4.77 out of 5 average rating, 153 reviews

Villa in Lowlands

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

LocationFamilyBathroom

5.0 out of 5 average rating, 34 reviews

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.

Villa in Indigo Bay

Life's Good

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Luxury villa rentals

Villa in Les Terrasses de Cul de Sac

Water access, heated pool, kayaks & snorkeling

FamilyLocationBack garden

4.98 out of 5 average rating, 46 reviews

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, 38 reviews

Beach-Private Pool-2 Master King Bedrooms

LocationComfortOutdoor spaces

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, 71 reviews

Private Orient Bay Villa with Spectacular Views

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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

LocationFamilyGetting around

4.98 out of 5 average rating, 47 reviews

A spacious wooden deck surrounds an inviting pool, offering views of shallow turquoise waters and nearby islands. Several lounge chairs are arranged for relaxation, while tropical palm trees gently sway in the breeze, enhancing the serene outdoor setting.

5.0 out of 5 average rating, 42 reviews

Villa Ti Case • Waterfront, water access & kayaks

FamilyLocationKitchen

5.0 out of 5 average rating, 14 reviews

Villa in Mont choisy

Sunset View – Steps from Friar’s & Happy Bay

LocationFamilyComfort

5.0 out of 5 average rating, 9 reviews

Villa in Oyster Pond

Villa Posidonie — Luxury Living by the Sea

LocationFamilyAccuracy

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 - Villa de luxe vue mer époustouflante 4 ch

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Villa rentals with a pool

4.69 out of 5 average rating, 16 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

Séjour idyllique entre mer-ciel-réserve naturelle

FamilyLocationPool

4.9 out of 5 average rating, 41 reviews

Little Paradise 2, piscine privée, vue magnifique

LocationFamilyKitchen

4.96 out of 5 average rating, 27 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

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A serene pool area is surrounded by a wooden deck, featuring sun loungers. The turquoise water of the pool reflects the bright blue sky, scattered with white clouds. Lush greenery and palm trees frame the scene, providing a tranquil atmosphere.

4.95 out of 5 average rating, 79 reviews

Slowlife Harmony - Caribbean Villa Three Bedrooms!

FamilyLocationPool

5.0 out of 5 average rating, 17 reviews

villa Koala, piscine chauffée, vue mer, Cul de Sac

ValueFamilyPool

Villa in Les Terres Basses

Villa Plum Bay

LocationFamilyOutdoor spaces

4.95 out of 5 average rating, 19 reviews

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

LocationFamilyNearby

4.88 out of 5 average rating, 24 reviews