
Villa holiday rentals in Upper Prince's Quarter
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Top-rated villa rentals in Upper Prince's Quarter
Guests agree: these villas are highly rated for location, cleanliness and more.

Ultra Modern Tropical Villa with stunning sea view
Our Villa overlooks the Ocean with 210 degree views, including St. Barts. Views from every room. Private and secure, the villa is suitable for an extended family or three/four couples - rooms are well separated. The wind provides a steady cooling breeze on the Atlantic side of the island. Open the sliding door in the morning and enjoy the topical breeze all day. Located on the prestigious quiet peaceful Plateau, a small gated community of 6 homes. Includes backup Diesel generator.

Villa Seascapes, Stunning 180° Ocean view
Villa Seascapes is a fully renovated luxury 4 bedroom villa with a 180 degree unobstructed ocean view, surrounded by a lush garden. (3 bedroom option available for booking - it is a different listing) 7min walk to Dawn beach, bar and restaurant. Salt water infinity pool. Large terrace overlooking the ocean. EACH of our 4rooms have private bathroom, walk in closet and magnificent ocean view. Bedroom 4 is fully private with own entrance, kitchen and living room. Instagr@m: @Seascapes_sxm

Palm Paradise - Tropical Villa in Oyster Pond
Welcome to Palm Paradise! This 4-bedroom, 4.5-bathroom villa in Oyster Pond, Sint Maarten, is your perfect Caribbean getaway. Sleeps 10 guests, featuring a private pool, backup generator, and fully equipped kitchen. One bedroom is in the separate Coconut Cottage, with its own kitchen and living room. This villa is ideal for families or groups. Enjoy modern amenities, outdoor dining and lounging, and a newly renovated interior. Your tropical oasis awaits—book now for an unforgettable stay!

Luxe 3BR Villa: Pool & Sweeping Ocean Views
Discover Villa Kyash, an architectural gem where your private infinity pool dissolves into the endless horizon. This flawlessly designed 3-bedroom, 3-bathroom sanctuary in tranquil Dawn Beach perfects the art of indoor-outdoor living. Sun-drenched terraces with a gourmet grill give way to a serene, air-conditioned interior where three king bedrooms ensure ultimate privacy. Curated for discerning families or groups, this is where luxury and tranquility become your reality.

Modern Bungalow With Pool - 3 Min Walk To Beach
Immerse yourself in nature during your stay at The Bungalow, a tropical open-air villa perched amongst the trees on the island of Anguilla. Enjoy breath-taking ocean views from your private pool, take a quick walk down to the beach for a dip in Rendezvous Bay, and wind down while watching the sunset from your expansive roof deck. Nature lovers will delight in the property’s indoor-outdoor feel, surrounded by lush gardens and with visits from native birds.

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 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

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.

Villa Sea Fan with Resort Amenities
✨Sea Fan with IRE Vacations ✨ This luxury 3 bedroom villa offers a comfortable modern floor plan with travertine flooring throughout, a fully equipped kitchen, and spacious indoor-outdoor living areas. Guests can enjoy the private pool, outdoor dining area, and access to resort amenities including a gym and spa. Perfect for a serene and upscale Caribbean getaway.

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.

Barefoot Villas GreatBay View in Hot Tub & Balcony
Wake up to stunning panoramic views of Philipsburg and Great Bay. Sip your morning coffee as cruise ships glide into port, all while soaking in the refreshing ocean breeze. This centrally located property puts you just minutes away from Philipsburg’s vibrant shopping scene, local supermarkets, restaurants, and some of the island’s best beaches.
Popular amenities for villa rentals in Upper Prince's Quarter
Private villa rentals

Villa Tropical Heaven

Waterfront "Bonjour" Beacon Hill St Maarten

Slowlife Harmony - Caribbean Villa Three Bedrooms!

Villa Pure • 3BR waterfront with kayaks, Wi-Fi, AC

Secret Harbor Villa, private escape in Anse Marcel

Bayview Resort, Beachfront villa w/ Stunning Views

Water access, heated pool, kayaks & snorkeling

Villa Pineapple - Grand Case Area -5mn Orient Bay
Luxury villa rentals

NEW Les Terres Basses - Villa Coco Paillette - Sxm

Luxury villa, swimming pool and panoramic sea view

Villa SEA VIEW, 5' from Grand Case beach, privacy

Villa Plum Bay

Villa with sea view and heated pool

Caribbean View Villa - Sea - Sunset - Location#1

Villa Litchi | Collection Villas Saint-Martin

Sunset View – Steps from Friar’s & Happy Bay
Villa rentals with a pool

Luxury Villa - Best Views in the Caribbean!

Villa Kyanéa | Face à l’océan · Piscine privée

Charming 3-Bed Villa in Maho

Ocean View Villa Little Bay

modern Villa with sea view at 2 mn from the beach

Carpe Diem, beautiful villa

A heavenly Sint Maarten's retreat

Villa Amanti Waterfront Paradise For Boat Lovers
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 | $1,212 SGD | $1,019 SGD | $1,096 SGD | $988 SGD | $905 SGD | $986 SGD | $1,003 SGD | $899 SGD | $845 SGD | $910 SGD | $910 SGD | $1,292 SGD |
| 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 villa rentals in Upper Prince's Quarter

Total holiday rentals
Explore 50 holiday rentals in Upper Prince's Quarter

Nightly prices starting at
Upper Prince's Quarter holiday rentals start at $244 SGD per night before taxes and fees

Verified guest reviews
Over 970 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
50 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

4.9 Average rating
Upper Prince's Quarter stays are highly rated by guests – averaging 4.9 out of 5!
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