
Villa holiday rentals in Upper Prince's Quarter
Find and book unique villas on Airbnb
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 $251 NZD per night before taxes and fees

Verified guest reviews
Over 1,240 verified reviews to help you choose

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

Pet-friendly accommodation
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

Wi-Fi availability
50 of Upper Prince's Quarter holiday 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 villa rentals in Upper Prince's Quarter
Guests agree: These villas are highly rated for location, cleanliness and more.

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 - different listing) 10min walk to Dawn beach. Salt water infinity pool. Large terrace overlooking the ocean. EACH bedroom has en-suite, walk in closet and ocean view. Bedroom 4 is fully private with own entrance, kitchen and living room Instagr@m: @Seascapes_sxm Total price includes cleaning fees and 15.5% Air BNB fee

Ocean View Villa Little Bay
🌴 Villa Little Bay – Oceanview Bliss With 360° Views Enjoy the peaceful sound of the waves and a serene, private atmosphere that’s still close to everything. We’re located within walking distance to Philipsburg, the vibrant heart of SXM—Front Street, top shopping, restaurants, and the island’s best casinos. The beach is just 5 minutes away, Step outside to your private patio for sunbathing, and shimmering ocean‑view pool. Villa offers the perfect blend of tranquility and convenience.

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!

Life's Good
Located in the only planned community in Sint Maarten in the beautiful and gated “Indigo Bay”. The whole villa to yourself and just 10 minutes from the airport. Villa "Life’s Good" with infinity pool is located on the mountainside with a 180 degree view of the sea and view of the Islands, Saba, St Kitts & Nevis and Sint Eustatius.. A spectacle of breathtaking sunrises and sunsets. Just a 3 minute drive from the villa: are beaches, restaurants and all amenities.

VILLA I LOVE VIEW – Luxury villa with sea view
Villa I LOVE VIEW is an oasis of tranquility – with its private pool (naturism possible), large terrace and luxurious kitchen area. Come and discover its view with multiple shades of blue while relaxing on the deckchairs by the pool with zen natural stone reflections Located in Cul de Sac, facing Saint Barth, Pinel Island and the Eastern Bay. Close to the most beautiful beaches of the island, restaurants, water sports, it is the ideal place for your vacation.

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 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.

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.

Brand new! - Slowlife - Enjoy Villa
Completely NEW Villa!! Enjoy is a beautiful house that we «placed» on the sand. Thinking on every detail for your greatest comfort, you will appreciate its unique location, an exceptional interior design, and its extraordinary outdoor spaces. In the very exclusive and secure residence of Terre Basses, very close to the beach of Baie Longue, experience an incomparable holiday.

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.

Villa Marant - Elegant Luxury Caribbean Escape
Experience the perfect blend of elegance and comfort at Villa Marant, where modern design meets tranquil relaxation. Nestled in a prime location, our villa offers a stylish retreat for travelers seeking the ultimate escape. Plus, with a backup generator in place, you’ll never have to worry about power outages—your comfort is always ensured.
Popular amenities for Upper Prince's Quarter villa rentals
Private villa rentals

Villa Kyanéa | Ocean View St. Barth · Private Pool

Bella Vista - Pool & sea view, 5 minutes from Grand Case

Villa Ocean - Indulge Yourself in Paradise

Only Villa with private beach Beach Villa Cala Mar

Villa Elysian in Indigo Bay

Private Orient Bay Villa with Spectacular Views

Villa Indigo Dream, Indigo Bay SXM

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

Your Paradise Villa

Slowlife Harmony - Caribbean Villa Three Bedrooms!

Beach-Private Pool-2 Master King Bedrooms

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

Belle Lurette • 3BR waterfront with kayaks, pool

OOF, Architect-designed house with sea view and private pool.

SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay

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

SeaDream Luxury Villa With Private Pool Indigo Bay

Little Paradise 2, private pool, beautiful view

Luxury villa, swimming pool and panoramic sea view

Villa Koala, heated pool, sea view, Cul de Sac

Modern 2 bedroom luxury beachside villa with pool

Villa Tibo

15% discount* until August 31, 2026: Villa Litchi

Villa Suzanne with sea view 4 bedrooms - 8 beds
When is the best time to visit Upper Prince's Quarter?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $1,647 NZD | $1,345 NZD | $1,447 NZD | $1,403 NZD | $1,274 NZD | $1,330 NZD | $1,308 NZD | $1,172 NZD | $1,102 NZD | $1,187 NZD | $1,187 NZD | $1,686 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 |
Destinations to explore
- Waterfront rentals Upper Prince's Quarter
- Rentals with a hot tub Upper Prince's Quarter
- Serviced apartment rentals Upper Prince's Quarter
- House rentals Upper Prince's Quarter
- Rentals with beach access Upper Prince's Quarter
- Apartment rentals Upper Prince's Quarter
- Rentals with pools Upper Prince's Quarter
- Family-friendly rentals Upper Prince's Quarter
- Luxury rentals Upper Prince's Quarter
- Beachfront rentals Upper Prince's Quarter
- Pet-friendly rentals Upper Prince's Quarter
- Condo rentals Upper Prince's Quarter
- Villa rentals Sint Maarten





