
Holiday rentals with a pool in Upper Prince's Quarter
Find and book unique homes with a pool on Airbnb
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.

Cozy apartment, private pool & terrace
Charming apartment located opposite Pinel Island. In the heart of a cul-de-sac. Between Orient Bay & Grand Case, the two must-see beaches on our island for its gastronomy. Unforgettable experience for your taste buds against a backdrop of white sand & turquoise sea. New apartment, totally independent of "la maison des îles". Spacious and comfortable suite. Double bed. 100% cotton sheets and towels. Separate toilet. One step between the living room and the swimming pool and furnished terrace. Private areas.

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.

Aman Oceanview
The Aman Oceanview 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

EXQUISITE 5-STAR BEACHFRONT VILLA
Guaranteed to create a 5-Star experience! Fully air-conditioned 3 BR, 3 1/2 bath Beachfront Villa w/private pool. If you love the ocean & spectacular views, but fine living & comfort are important to you, we have it all! My home offers Personal housekeeper, Private Chef for hire, full Concierge Service, private garage, and gym. Also, food and groceries delivered prior to your arrival, access to all the services and amenities next door at the Oyster Bay Hotel.

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.

VILLA JADE 1: FEET IN THE WATER/POOL SUITE
VILLA JADE is located in the bay of "FRENCH CUL DE SAC". It is a beachfront complex consisting of 3 private villas. VILLA JADE 1 is a suite for 2 people with a private pool. The villas are quiet and private... your only view is the sea. The bay of "FRENCH CUL DE SAC" is 5 minutes from ORIENT BAY, touristy with restaurants, bars, water activities, but also a few minutes from GRAND CASE, our typical little village with gourmet restaurants by the sea....

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.

Modern house, cocktail pool, ocean view
Stay at a beautiful duplex home in Oyster Pond. With a cocktail pool, a breathtaking ocean view and a modern interior design, this spacious and fully equipped home is ideal for a couple. Enjoy the peace of the neighborhood and also benefit from a 24/7 gated security. This home will offer everything you need for an amazing stay in Sint Maarten / Saint Martin.

Breezy Bird - Charming Villa with private pool
✨ Villa Breezy Bird with IRE Vacations✨ (formerly Félicité) is truly a unique place. Recently renovated, it offers amazing views of the ocean and the Island of St. Barths. The living areas are truly indoor/outdoor. This villa is the perfect place to relax and enjoy a wonderful Caribbean holiday with breathtaking views.
Popular amenities for Upper Prince's Quarter rentals with a pool
House rentals with a pool

Ocean View Villa-Indigo Bay W/Private Pool/0 Steps

The best view on the island!

Luxury Bungalow with Amazing Seaview & Pool

LODGE Elegant Cocoon, Tropical Terrace, Sea View

Paradise View, Creole house with private pool

Préstige - Luxurious 3 bedroom by the Beach

Infinite Blue – Elegant Villa & Turquoise Views

Ocean view villa at Dawn beach
Condo rentals with a pool

Oceanfront studio on orient bay

Loft Condo - STEPS FROM BEACH!

1 bedroom apartment in the heart of Orient Bay

Feet in the ocean, Orient Bay, Beach apartment

Oceanfront w Pool | Maho Beach area

Beachfront Orient bay sea view condo 1 BR 4p

Studio Iguana

"SeaBird" studio, feet in the water on the beach
Other holiday rentals with a pool

Popular Beachfront Property Barefoot /Simpson bay

Blue Horizon Beach Bungalow

Water access, heated pool, kayaks & snorkeling

New! Accommodation in a residence with pool

Villa Litchi | Collection Villas Saint-Martin

Alamanda - Orient bay - Apartment Oceanview

Coconut, Anse Marcel, Beach & Pool

Love beach loft
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 | $749 NZD | $672 NZD | $870 NZD | $750 NZD | $749 NZD | $750 NZD | $749 NZD | $687 NZD | $682 NZD | $717 NZD | $747 NZD | $749 NZD |
| 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 |
Quick stats about holiday rentals with a pool in Upper Prince's Quarter

Total holiday rentals
Explore 370 holiday rentals in Upper Prince's Quarter

Nightly prices starting at
Upper Prince's Quarter holiday rentals start at $100 NZD per night before taxes and fees

Verified guest reviews
Over 2,650 verified reviews to help you choose

Family-friendly holiday rentals
290 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
190 properties have a dedicated workspace

Wi-Fi availability
360 of Upper Prince's Quarter holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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!
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