
Vacation 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.

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.

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.

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

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

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"......

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.

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

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

Spacious 3BR with Private Cozy Pool

Villa close to the beach

Miracle on the Bay

Villa Bahia

Villa Tamarind | Luxury | Spectacular Views | 4BDR

Villa Leones spectacular view, authentic charm

Villa Pandora
Condo rentals with a pool

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub

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

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

cosy apartment

Green Lemon - A Seaside Garden

Princess Mahault, Orient Bay, pool, on the beach

Seneca Condo

2 Bed Suite in Condo Hotel, Ocean view, Concierge
Other vacation rentals with a pool

Life's Good

Villa Kyanéa | St. Barth Ocean View · Private Pool

Bella Vista – Pool & Sea View, 5 Minutes from Grand Case

EXQUISITE 5-STAR BEACHFRONT VILLA

Sea View Studio with Infinity Pool – Romantic Stay

CONDOstmaarten panoramic (Adults Only)

The Loft at Simpson Bay Yacht Club

CONDOSTmaarten by the sea (Adults Only)
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$97,903 GYD | G$94,137 GYD | G$83,677 GYD | G$94,346 GYD | G$94,137 GYD | G$94,346 GYD | G$94,137 GYD | G$86,397 GYD | G$85,769 GYD | G$90,162 GYD | G$93,928 GYD | G$94,137 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 |
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$12,552 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!
Destinations to explore
- Fitness-friendly rentals Upper Prince's Quarter
- Pet-friendly rentals Upper Prince's Quarter
- Smoking-friendly rentals Upper Prince's Quarter
- Waterfront rentals Upper Prince's Quarter
- Villa rentals Upper Prince's Quarter
- Condo rentals Upper Prince's Quarter
- Beachfront rentals Upper Prince's Quarter
- Rentals with beach access Upper Prince's Quarter
- Rentals with a washer and dryer Upper Prince's Quarter
- Apartment rentals Upper Prince's Quarter
- Luxury rentals Upper Prince's Quarter
- Rentals with a patio Upper Prince's Quarter
- Family-friendly rentals Upper Prince's Quarter
- Rentals with a hot tub Upper Prince's Quarter
- Serviced apartment rentals Upper Prince's Quarter
- Rentals with outdoor seating Upper Prince's Quarter
- House rentals Upper Prince's Quarter
- Rentals with pools Sint Maarten





