
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 €131 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 & 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

4.8 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.

Oceanfront Guana Bay Villa with View of St. Barts
This contemporary oceanfront Villa is fully air conditioned and overlooks both Guana Bay & the Atlantic Ocean. Spectacular morning views of the sunrise and panoramic views of St. Barts. Villa Star has been newly renovated in 2025. Luxury 2 BR/2 BA with high tech fixtures. This gorgeous Villa has full cooking facilities, living area, dedicated workspace & wrap-around deck. A 5 minute drive to both Philipsburg and the French side. Tranquil and exclusive neighborhood. This truly is paradise!
4.82 out of 5 average rating, 91 reviews
Ocean Pearl - Spacious Villa in Dawn Beach
Welcome to our stunning & modern villa in the gated community of Dawn Beach! This spacious retreat offers 6 large, comfy bedrooms (4-bedroom option available), with gorgeous bathrooms. Relax in the huge open plan living/dining area and updated kitchen. Step out to the expansive patio with an infinity pool and breathtaking views of both the Dutch and French sides. Plus, a backup generator ensures your stay is hassle-free. 2-car garage and extra parking included. Perfect for your island getaway!
5.0 out of 5 average rating, 18 reviews
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.
5.0 out of 5 average rating, 19 reviews
Beachfront/6 bdrs en-suite/ Maid included (h)
This impressive beachfront luxurious villa, direct private access to the beach, is located in Guana Bay, offering large & spacious living space, with terrace, patio & pool. There are 6 bedrooms, each with en-suite bathrooms. 5 bedrooms with king size beds & 1 bedroom with 2 twin beds. Daily maid service (max 4h) is included. Secure area, quiet place, the villa offers BBQ & games. Ideal for friends & families. COVID Thermometer. 24/7 Maintenance & service. Meeting at car rentals possible.
5.0 out of 5 average rating, 16 reviews
AZUR 4BR 4.5BA Walk to Indigo Beach- Sea Side Dr.
Welcome to AZUR, the newest luxury villa at Indigo Bay, Sint Maarten. Stunning property features 4 BR, 4.5 BA each with a king bed, and en-suite full baths and fitted wardrobes. Guests can enjoy inside and outside dining, each room controlled AC , WiFi, Infinity pool, 3 large terraces, BBQ grill, rooftop lounge, tropical garden, turquoise sea, and sunsets. This captivating spacious villa has gourmet kitchen with island for casual dining. AZUR is your exclusive sanctuary by the sea.
4.83 out of 5 average rating, 18 reviews
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.
5.0 out of 5 average rating, 110 reviews
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
4.85 out of 5 average rating, 157 reviews
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.
4.99 out of 5 average rating, 94 reviews
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.
4.93 out of 5 average rating, 73 reviews
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.
4.99 out of 5 average rating, 105 reviews
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.
4.93 out of 5 average rating, 27 reviews
VILLA JADE 2: WATERFRONT SUITE/POOL
VILLA JADE is a complex of 3 villas located in the bay of CUL DE SAC and its islets... VILLA JADE 2 is a spacious/sea view suite for 2 people on the water, with a private pool. The 3 villas are adjoining but very quiet and private. Your unique view is the sea... Direct access to the sea via a pontoon, and kayaks at your disposal.
4.99 out of 5 average rating, 160 reviewsPopular amenities for villa rentals in Upper Prince's Quarter
Private villa rentals

Villa Ocean - Indulge Yourself in Paradise
4.95 out of 5 average rating, 81 reviews
Villa Indigo Dream, Indigo Bay SXM
4.81 out of 5 average rating, 94 reviews
Sea view 3BR Spring Sea Villa w/ pool, St Maarten
4.85 out of 5 average rating, 33 reviews
Villa Kyanéa | Ocean View, St Barth · Private Pool
4.94 out of 5 average rating, 32 reviews
SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay
4.77 out of 5 average rating, 154 reviews
Villa Solandra – 3BR Oceanfront Sunset w/ Pool
4.94 out of 5 average rating, 49 reviews
Villa Elysian in Indigo Bay
4.91 out of 5 average rating, 55 reviews
Life's Good
5.0 out of 5 average rating, 35 reviewsLuxury villa rentals

Beach-Private Pool-2 Master King Bedrooms
4.97 out of 5 average rating, 38 reviews
Sunset View – Steps from Friar’s & Happy Bay
5.0 out of 5 average rating, 14 reviews
NEW Les Terres Basses - Villa Coco Paillette - Sxm
4.91 out of 5 average rating, 11 reviews
Belle Lurette • 3BR waterfront with kayaks, pool
5.0 out of 5 average rating, 16 reviews
A heavenly Sint Maarten's retreat
4.7 out of 5 average rating, 46 reviews
Villa Posidonie — Luxury Living by the Sea
5.0 out of 5 average rating, 9 reviews
Brand new! - Slowlife - Enjoy Villa
4.98 out of 5 average rating, 47 reviews
Villa Ti Case • Waterfront, water access & kayaks
5.0 out of 5 average rating, 42 reviewsVilla rentals with a pool

Spacious Villa - Saint Martin - Pool & 4 Bedrooms
4.97 out of 5 average rating, 66 reviews
Idyllic getaway between sea, sky and nature reserve
4.69 out of 5 average rating, 16 reviews
Private villa / beautiful View next to La Samanna
4.88 out of 5 average rating, 24 reviews
Modern 2 bedroom luxury beachside villa with pool
4.87 out of 5 average rating, 89 reviews
Villa Koala, heated pool, sea view, Cul de Sac
5.0 out of 5 average rating, 17 reviews
Villa Plum Bay
4.95 out of 5 average rating, 19 reviews
Wonderfull 180° view, from Orient Bay to Pinel
4.96 out of 5 average rating, 51 reviews
Villa Pure • 3BR waterfront with kayaks, Wi-Fi, AC
5.0 out of 5 average rating, 36 reviewsWhen 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 | €858 | €700 | €753 | €730 | €663 | €692 | €681 | €610 | €574 | €618 | €618 | €878 |
| 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
- Flat rentals Upper Prince's Quarter
- Rentals with pools Upper Prince's Quarter
- Luxury rentals Upper Prince's Quarter
- Family-friendly rentals Upper Prince's Quarter
- Beachfront rentals Upper Prince's Quarter
- Pet-friendly rentals Upper Prince's Quarter
- Apartment rentals Upper Prince's Quarter
- Villa rentals Sint Maarten





