Vacation rentals in Upper Prince's Quarter

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Top-rated vacation rentals in Upper Prince's Quarter

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Guest favourite

Apartment in Upper Prince's Quarter

5.0 out of 5 average rating, 23 reviews

Stylish apartment w/ POOL & stunning views

Come stay with us! You will arrive to our beautifully decorated 1 bedroom apartment nestled in the hills of Guana Bay with a pool, stunning views,WIFI, Live TV and conveniently located minutes away from Philipsburg, beaches, restaurants, bars, supermarkets, shops and casinos. The hills is very private with your own balcony and separate entrance and offers the perfect accommodation and value with breathtaking panoramic views on the balcony. Perfect for couples, solo and business travelers alike.

Apr. 10 – 17

$208 CAD per night

Guest favourite

Villa in Upper Prince's Quarter, Sint Maarten

5.0 out of 5 average rating, 36 reviews

EXQUISITE 5-STAR BEACHFRONT VILLA

SPECIAL: MARCH 18-30 @ $800/NIGHT Guaranteed to create a 5-Star experience! Fully air-conditioned 3 BR, 3 1/2 bath Beachfront Villa w/private pool. If you love the ocean & spectacular views, but fine living & comfort are important to you, we have it all! My home offers Personal housekeeper, Private Chef for hire, full Concierge Service, private garage, and gym. Also, food and groceries delivered prior to your arrival, access to all the services and amenities next door at the Oyster Bay Hotel.

Aug. 25 – Sep. 1

$1,373 CAD per night

Superhost

Home in Upper Prince's Quarter

5.0 out of 5 average rating, 4 reviews

Teresa’s Ocean Paradise

St. Maarten’s best kept secret with spectacular 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.

Mar. 15 – 22

$465 CAD per night

Guest favourite

Villa in Upper Prince's Quarter, Sint Maarten

4.96 out of 5 average rating, 99 reviews

The Blue Door Villa - 4 bed ocean view home

Welcome to The Blue Door Villa where 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 to help plan your vacation.

Aug. 2 – 9

$1,285 CAD per night

Guest favourite

Villa in Upper Prince's Quarter, Sint Maarten

5.0 out of 5 average rating, 22 reviews

Villa Blue Roc

Cette villa luxueuse , est situee dans une residence securisee avec une vue epoustouflante , face a l ocean et l ile de St Barthelemy, Perchee sur les hauteurs de Dawn Beach, a 15 minutes des fameuses plages/restaurants d Orient Bay et Grand Case en partie francaise. La villa est egalement a 5 minutes de la capital hollandaise , Philipsburg, un incontournable du shopping. Grace aux grands espaces exterieurs et a la piscine a debordement , cette villa vous offrira un sejour inoubliable.

Feb. 21 – 28

$1,174 CAD per night

Guest favourite

Apartment in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 172 reviews

The Beach House Apartment

A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more

Sep. 29 – Oct. 6

$424 CAD per night

Guest favourite

Apartment in Oyster Pond, St. Martin

4.9 out of 5 average rating, 97 reviews

Lovely Studio Apartment with Pool & Nature Views!

Take a break and unwind at this peaceful studio apartment, perfect for your Caribbean getaway! This fully equipped studio is located just 7-10 minutes away from the capital, Philipsburg, and a few minutes away from several beautiful beaches. It also has gorgeous scenic views and an inviting and relaxing pool! As well as a rooftop terrace with scenic 360 views. Baby crib and grill available upon request for small fee and washer & dryer available on premise for free use.

Nov. 2 – 9

$137 CAD per night

Guest favourite

Villa in Oyster Pond , Sint Maarten

5.0 out of 5 average rating, 32 reviews

Ultra Modern Tropical Villa w. stunning sea views

Villa Helios 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 and peaceful Plateau, a small gated community of only 6 homes.

Apr. 25 – May 2

$1,138 CAD per night

Guest favourite

Apartment in Philipsburg

4.98 out of 5 average rating, 123 reviews

Bayside Walk beachfront apartment

This modernly decorated apartment home is centrally located in the capital of the Dutch side, Philipsburg. The area is full of life during the day and quiet and relaxing in the evening. This home away from home will make your daydreams of island life a reality. Enjoy the lovely courtyard garden downstairs, relax on the balcony looking out to the beautiful garden and plan your day’s adventure on and around this dual nation Island.

Aug. 12 – 19

$252 CAD per night

Guest favourite

Apartment in Little Bay

4.98 out of 5 average rating, 113 reviews

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 !

Aug. 2 – 9

$513 CAD per night

Guest favourite

Apartment in Marigot, St. Martin

4.89 out of 5 average rating, 28 reviews

Pearl of Coco in Oyster Pond

Charming apartment set in the peaceful village of Oyster Pond in a small, quiet residence. Refurbished, fully equipped, comfortable with quality bedding, air-conditioned room + 1 sofa bed with air mixer on the ceiling. Its breathtaking view of the lagoon is ideal for sunrise breakfasts. Pool overlooking the available lagoon 24h/24. Restaurants and shops 3 min walk away. Beaches nearby.

Sep. 15 – 22

$156 CAD per night

Guest favourite

Apartment in Upper Prince's Quarter, Sint Maarten

4.96 out of 5 average rating, 57 reviews

Apartment in tranquil, gated community.

This is a quiet and comfortable appartement with private parking and entrance. It sits in a large garden including a BBQ place. It is a modern appartement and the location is inside a gated community. It is underneath our own living space, so we are nearby for questions and extra assistance. The bed is the equivalent size of Californian King.

Nov. 8 – 15

$133 CAD per night