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Vacation rentals with a pool in Upper Prince's Quarter

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Top-rated rentals with a pool in Upper Prince's Quarter

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
An open-plan living area showcases a modern kitchen with a marble countertop and sleek cabinetry. Large glass doors provide expansive ocean views and access to an outdoor terrace. A comfortable seating area includes neutral-toned furnishings, while dining space is set for meals with panoramic vistas.
Home in Upper Prince's Quarter
5 out of 5 average rating, 25 reviews

Sunrise Over St. Barths

BRAND NEW CONDO in a quiet gated community! "Sunrise Over St. Barths" is an oasis of luxury and elegance, built into the hillside overlooking the Atlantic Ocean and St Barth. Enjoy the sunrise every morning in this modern property consisting of 2 master bedrooms with 2 bathrooms, living room with fully equipped kitchen, exterior terrace and laundry area. Each bedroom and the living room have unobstructed panoramic views of the ocean. A breathtaking infinity pool and a sundeck overlook the ocean.

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
4.95 out of 5 average rating, 63 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.

Top guest favorite
Home in Philipsburg
5 out of 5 average rating, 25 reviews

Stunning Panoramic Views Of The Ocean & St Barth!

“Villa Senorita” is located in the private residential and secured Mandara Residences. This brand new modern condominium features 164sqm/1766 sqft of interior and exterior space with WIFI throughout. The Condo consists of two master bedrooms with two bathrooms, living room with kitchen area, exterior terrace, and laundry area. All two bedrooms, the living room have unobstructed and breathtaking views of the ocean, Guana Bay Beach, Saint Barthélémy and the beautiful island nature.

Guest favorite
Apartment in Upper Prince's Quarter
5 out of 5 average rating, 12 reviews

Aman_Sky

The unique Aman_Sky 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

Top guest favorite
Villa in Upper Prince's Quarter
4.94 out of 5 average rating, 79 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.

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
4.95 out of 5 average rating, 118 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.

Top guest favorite
An outdoor terrace features comfortable white lounge furniture arranged around a coffee table. Sun loungers are positioned beside a private infinity pool, overlooking the ocean and distant boats. The scene is framed by tropical plants and a clear blue sky, enhancing the serene coastal environment.
Loft in Marigot
4.99 out of 5 average rating, 185 reviews

Sea Loft, Breathtaking View – Private Pool

* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with lounge chairs, garden furniture, outdoor table and BBQ * Office area * 100 Mbps Wi-Fi * TV with thousands of channels from around the world * 250 m walk to Fort Louis de Marigot Marina * 5 min walk to Marigot city center with its restaurants, boutiques and other shops * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

Guest favorite
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.
Villa in Cul-de-Sac
4.95 out of 5 average rating, 127 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"......

Top guest favorite
The living room features large glass doors that open to stunning ocean views. A spacious gray sofa with decorative pillows is positioned around a white coffee table. Natural light fills the area, complemented by light curtains and a blue accent chair.
Condo in Upper Prince's Quarter
5 out of 5 average rating, 27 reviews

The Coastal Condo: Beautiful Luxury 3 Bed 2.5 bath

Stylish and spacious condo located in a quiet neighborhood . This unit offers sweeping Atlantic Ocean views, wrap around balcony, a modern kitchen with breakfast bar, comfortable lounge living room, TV with Netflix access, dining area with seating for 6, spacious bedrooms and baths, free private parking and a gorgeous infinity pool. It is ideal for couples and families alike. WE HAVE A BACK UP GENERATOR that keeps the power on all the times

Top guest favorite
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.
Villa in Upper Prince's Quarter
4.99 out of 5 average rating, 81 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.

Top guest favorite
A private heated pool is featured at the edge of the terrace, offering views of the ocean and nearby islands. The clear blue water contrasts with the light-colored stone surrounding the pool, while lush greenery can be seen in the background against a clear sky.
Apartment in Little Bay
4.99 out of 5 average rating, 172 reviews

Stunning 2 BD Ocean View - Terraces Lt Bay

Treat yourself to the utmost stylish and modern ocean view apartment located in the exclusive Little Bay Hill . This spacious environment, is designed to be enjoyed as a family, has a terrace with stunning sea views, private pool, one master suites ( Japanese king bed and a walking closet), one bedroom suite with two twin size beds ( could be converted to king size bed ) . Welcome to Terraces Little Bay !

Top guest favorite
An inviting outdoor space features a private pool surrounded by lush greenery and sea views. Comfortable lounge chairs are positioned nearby, providing a serene spot to relax. Sunlight reflects off the water's surface, creating a tranquil atmosphere.
Apartment in Indigo bay
4.94 out of 5 average rating, 125 reviews

Independent apartment at the bottom of the villa – Indigo Bay

The Villa Stella apartment welcomes you in a unique setting with spectacular views of the Caribbean Sea. Located in a 24-hour secure residence, tranquility awaits. You will be just an 8-minute walk to Indigo Bay Beach and close to shops and restaurants in the Dutch side. Composed of 2 bedrooms and 2 bathrooms, you can relax in the pool/jacuzzi overlooking the bay.

Popular amenities for Upper Prince's Quarter rentals with a pool

When is the best time to visit Upper Prince's Quarter?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$94,044 GYDG$84,430 GYDG$109,300 GYDG$94,253 GYDG$94,044 GYDG$94,253 GYDG$94,044 GYDG$86,311 GYDG$85,684 GYDG$90,073 GYDG$93,835 GYDG$94,044 GYD
Avg. temp26°C26°C26°C27°C28°C29°C29°C29°C29°C29°C28°C27°C

Quick stats about vacation rentals with a pool in Upper Prince's Quarter

  • Total vacation rentals

    Explore 390 vacation rentals in Upper Prince's Quarter

  • Nightly prices starting at

    Upper Prince's Quarter vacation rentals start at G$12,539 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,100 verified reviews to help you choose

  • Family-friendly vacation rentals

    310 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    200 properties have a dedicated workspace

  • Wi-Fi availability

    380 of Upper Prince's Quarter vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Upper Prince's Quarter rentals

  • 4.8 Average rating

    Upper Prince's Quarter stays are highly rated by guests—averaging 4.8 out of 5!