
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.

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 Sophia: Oceanfront w/ Generator & Pool
Welcome to Villa Sophia, a stunning, luxurious, and elegant 4-bedroom oceanfront villa in Tamarind Hill Estates, combining the best of indoor and outdoor living in traditional St. Maarten style. Expansive sea views, a private pool, and tons of amenities. Just minutes from Great Bay Beach, Philipsburg, and the island’s best attractions, Villa Sophia is ideal for families and groups seeking a unique, and unforgettable Caribbean retreat. Book your stay and enjoy a luxury experience in paradise!

Guana Bay Beach Condo
It's all about the views at the Guana Bay Beach Condo! With a wrap around balcony on the second floor, you are sure to enjoy the sunrises and views of St. Bart's and the Atlantic Ocean. Just a 2 minute walk to a very private spectacular beach. The condo is very comfortable with one bedroom, one and a half bathrooms, fully stocked kitchen. It also includes AC and a washer/dryer for your convenience and a fully stocked kitchen. Downtown Philipsburg is just a 5 minute drive away.

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

Secret View amazing apartment- Private pool
Welcome to Secret View, a stunning, fully renovated, stylish and modern apartment located directly on the lagoon with a private pool and breathtaking views. Quiet and secure area, next by Maho, Mullet Bay, the golf course, supermarket, bars, restaurants, and casinos. A true sanctuary, it’s sure to be the highlight of your holiday. Private and free parking Your ultimate vacation retreat. Sint Maarten is currently experiencing some daily power outages

THE HILL HOUSE, 2 Bdr, pool, panoramic view
Accommodation with private pool and breathtaking views Treat yourself to a dream break at this stylish home, nestled in the secure Almond Grove Estate neighborhood. Enjoy 2 air-conditioned bedrooms, a bright living room, a full kitchen, and especially an idyllic outdoor space with a pool and panoramic views of Simpson Bay. Just 5 min from Marigot, 10 min from the airport and 15 min from the beaches, it is the perfect address for an unforgettable stay!

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.

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.

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 deckchairs, garden furniture, outdoor table and BBQ * Office space * 100 Mbps WiFi * 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, shops and other stores * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

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.

"La Vue SXM" Luxe "Villa La Vue" + Beach / Bar / Food
Located in private gated community Indigo Bay, minutes from beach. Villa has private infinity pool and is neighbored by large communal pool. Modern art déco 2 floor villa has 3 bedrooms, 3 full bathrooms, equipped kitchen, balcony, and terrace with ocean views. **Construction of new hotel began in Indigo Bay as of March 2025 which impacts the entire bay** Free : - Champagne on arrival - 1 Mid Housekeeping Services
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

Ocean Pearl - Spacious Villa in Dawn Beach

Villa close to the beach

New-Sunset Place Villa w Stunning Waterfront Views

The best view on the island!

Paradise View, Creole house with private pool

Cocon Lodge Elegant, Tropical Terrace, Sea View

Préstige - Luxurious 3 bedroom by the Beach
Apartment rentals with a pool

Oceanfront w Pool | Maho Beach area

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

Beachfront Condo| Pool View + Private Beach Access

cosy apartment

New studio with superb view of the Caribbean Sea

Seneca Condo

Casa Nova, Indigo Bay SXM

NEW on the heights of Orient Bay beach unit for 4p
Other holiday rentals with a pool

Oceanfront Guana Bay Villa with View of St. Barts

Ultra Modern Tropical Villa with stunning sea view

magnificent Orient Bay sea view apartment

Water access, heated pool, kayaks & snorkeling

Villa Indigo Dream, Indigo Bay SXM

Buddha Gardens Studio B

1 bedroom with loft murphy bed

Sea View Studio with Infinity Pool – Romantic Stay
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 | £342 | £307 | £397 | £343 | £342 | £343 | £347 | £314 | £312 | £304 | £304 | £342 | 
| 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 380 holiday rentals in Upper Prince's Quarter 
 - Nightly prices starting at- Upper Prince's Quarter holiday rentals start at £46 per night before taxes and fees 
 - Verified guest reviews- Over 2,640 verified reviews to help you choose 
 - Family-friendly holiday rentals- 300 properties offer extra space & child-friendly amenities 
 - Pet-friendly holiday rentals- Find 40 rentals that welcome pets 
 - Rentals with dedicated workspaces- 200 properties have a dedicated workspace 
 - Wifi availability- 370 of Upper Prince's Quarter holiday rentals include wifi 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! 
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- Rentals with pools Sint Maarten
