
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$12,546 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.

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.

Villa Mango SXM 3BD • Ocean View • Modern • Pool
Wake up to sweeping ocean views of St. Barths, Saba, St. Kitts & Nevis, and Anguilla. Enjoy your morning coffee poolside in the ocean breeze or stroll through the villa’s lush private tropical gardens Inside, find a fully stocked gourmet kitchen perfect for entertaining and three king suites designed as a personal retreats—featuring private en-suite baths, luxury hotel-grade linens and individually controlled air conditioning - for ultimate privacy and comfort. A true luxury Villa experience

Horizon (Apt3) – Sea & Pool View, Terrace
Stylish triplex with 3 bedrooms, all with sea and pool view. Located in Black Palm, an elegant residence of 7 apartments in Indigo Bay, a calm and exclusive neighborhood. Indigo Beach is just a 5-minute walk away. Enjoy the shared pool with sea view. Ideal for up to 5 guests: couples, friends or families looking for relaxation. - 5 minutes’ walk from Indigo Beach - 5 minutes’ drive from the nearest supermarket - Private parking on site - Concierge service available for any request.

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.

Aman_Aria
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.

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.

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.

Breathtaking view of St Barth – 8 people
🛏️ King Size Bed 🌊 Incredible panoramic sea views 🏊 Heated pool 💧 Tank and generator for guaranteed comfort in all circumstances ❄️ Fully air conditioned 🛰️ Starlink Internet 🚗 Private parking ⚡ 110V and 220V 🔐 Secure residence with access gate 🔥 Gas barbecue 🧹 Complimentary housekeeping for stays of 6 nights or more 📺 International TV 🛁 Bedrooms and bathrooms with sea views 🌿 Not overlooked for complete privacy 🏡 New construction 2025

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

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 !

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
House rentals with a pool

Villa Paradis - The best views of the island!

Villa Coco

The best view on the island!

Miracle on the Bay

Villa Tamarind | Luxury | Spectacular Views | 4BDR

Préstige - Luxurious 3 bedroom by the Beach

Villa Leones spectacular view, authentic charm

Ocean view villa at Dawn beach
Condo rentals with a pool

Ocean View Residence

Five Star Luxury Beachfront Condo Private Hot Tub

"SeaBird" studio, feet in the water on the beach

Paradise Getaway With Best View of SXM!

Indigo~2 KingSuites, Priv Pool, 2 Min Walk 2 Beach

cosy apartment

Luxury 3 Bedroom Condo - Dawn Beach Club

Seneca Condo
Other vacation rentals with a pool

Life's Good

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

Brand new! - Slowlife - Enjoy Villa

Villa Kyanéa | St. Barth Ocean View · Private Pool

Ocean Dream Villa

Sea Haven Villa - Breathtaking Views of Dawn Beach

EXQUISITE 5-STAR BEACHFRONT VILLA

Ocean View Villa Little Bay
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$97,858 GYD | G$94,094 GYD | G$83,639 GYD | G$94,303 GYD | G$94,094 GYD | G$94,303 GYD | G$94,094 GYD | G$86,357 GYD | G$85,730 GYD | G$90,121 GYD | G$93,885 GYD | G$94,094 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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- Rentals with pools Sint Maarten





