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

Total vacation rentals
Explore 410 vacation rentals in Upper Prince's Quarter

Nightly prices starting at
Upper Prince's Quarter vacation rentals start at G$12,551 GYD per night before taxes and fees

Verified guest reviews
Over 3,590 verified reviews to help you choose

Family-friendly vacation rentals
320 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
210 properties have a dedicated workspace

Wi-Fi availability
400 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!
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.

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.
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Endless Views @ Acqua Bleu
Nestled in the heart of Saint Martin, Acqua Bleu offers breathtaking views of turquoise waters and pristine beaches. You'll have direct access to some of the most gorgeous spots on the island, ensuring endless fun in the sun. You’ll enjoy access to various amenities, including a fully equipped kitchen, spacious living areas, a refreshing swimming pool, and much more! Acqua Bleu features two king bedrooms, each accompanied by a private bathroom. Get ready to enjoy a truly rejuvenating vacation!
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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.
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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.
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Aman_Luna
The unique Aman_Luna 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
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Aman Serene - new listing
This unique place has a style all its own, newly built, contemporary retreat features two elegant master bedrooms, each with its own private bathroom, a spacious living area seamlessly connected to a fully equipped kitchen, an inviting outdoor terrace. Every bedroom and the living room offer uninterrupted vistas of the mesmerizing ocean. The heart of Aman is its spectacular infinity pool and sun-drenched deck, inviting you to relax while soaking in breathtaking panoramas.
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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.
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Serenity Seascape | 2BR Retreat, 270° Oceanviews
Wake up to a jaw-dropping panoramic view of the Caribbean Sea from this chic oceanfront gem in Point Blanche! Bask in 270° views, picture-perfect sunrises, and views of St. Barths from your own private terrace. The space features modern coastal interiors and hotel-quality bathrooms, blending luxury with cliffside serenity. Located just five minutes from Philipsburg, it offers easy access to beaches, restaurants, and shopping while preserving tranquility.
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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.
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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
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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
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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 !
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Popular amenities for Upper Prince's Quarter rentals with a pool
House rentals with a pool

ALMOND BLUE ...Pinel bay view - caribbean feeling
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Blue mornings, private pool, superb view
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Ocean view villa at Dawn beach
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Villa Tamarind | Luxury | Spectacular Views | 4BDR
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Villa ELIOS 2BR SeaView
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2 Bedroom Ocean Front Villa, Private Infinity Pool
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Villa Leones spectacular view, authentic charm
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Spacious 3BR with Private Cozy Pool
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Condo rentals with a pool

Horizon (Apt3) – Sea & Pool View, Terrace
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Green Lemon - A Seaside Garden
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"SeaBird" studio, feet in the water on the beach
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Beach front luxury! Huge 2BR that has it all! 😍🤩😍
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Sea view, Anse Marcel
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Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub
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Brand New- Maho Condo Studio with Seaview and Pool
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Ocean View Residence
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Other vacation rentals with a pool

Villa Marant - Elegant Luxury Caribbean Escape
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Sea Haven Villa - Breathtaking Views of Dawn Beach
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Ocean View Villa Little Bay
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Villa Mango SXM - Ocean View • Modern • 3BD • Pool
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Villa Ocean - Indulge Yourself in Paradise
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Villa Kyanéa | St. Barth Ocean View · Private Pool
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Sea view 3BR Spring Sea Villa w/ pool, St Maarten
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AZUR 4BR 4.5BA Walk to Indigo Beach- Sea Side Dr.
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When is the best time to visit Upper Prince's Quarter?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$97,901 GYD | G$94,136 GYD | G$83,676 GYD | G$83,676 GYD | G$83,676 GYD | G$83,676 GYD | G$94,136 GYD | G$86,396 GYD | G$85,768 GYD | G$90,161 GYD | G$93,927 GYD | G$94,136 GYD |
| Avg. temp | 26°C | 26°C | 26°C | 27°C | 28°C | 29°C | 29°C | 29°C | 29°C | 29°C | 28°C | 27°C |
Destinations to explore
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- Pet-friendly rentals Upper Prince's Quarter
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- Family-friendly rentals Upper Prince's Quarter
- Rentals with pools Sint Maarten





