Waterfront vacation rentals in Upper Prince's Quarter

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Top-rated waterfront accommodations in Upper Prince's Quarter

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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.

Sep. 26 – Oct. 3

$1,262 CAD per night

Guest favourite

Villa in Upper Prince's Quarter, Sint Maarten

4.9 out of 5 average rating, 10 reviews

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

Aug. 4 – 11

$1,096 CAD per night

Guest favourite

Home in Upper Prince's Quarter, Sint Maarten

5.0 out of 5 average rating, 59 reviews

Villa Tamarind | Luxury Oasis | Ocean views | 4BDR

Villa Tamarind is a unique luxury rental property. It truly is our home away from home and outfitted with fun and comfort in mind. We are located on the Dutch side, minutes from the French border, in a quiet gated community with the best views of the whole island. This is the perfect place to build memories with friends & family while you listen to the soothing sound of the waves, relax in the property's pool surrounded by swaying palms, and enjoy the villa's fantastic cooking equipment.

Sep. 4 – 11

$1,311 CAD per night

Guest favourite

Villa in Indigo Bay, Sint Maarten

4.95 out of 5 average rating, 100 reviews

Villa Life is Good

Sint Maarten Indigo Bay: One whole villa to yourself at 10 minutes from Princess Julianna airport the Villa "Life is Good" with infinity pool is located on the mountainside with a 180 degree view of the sea. View of the Islands, Saba, St Kitts & Nevis and Sint Eustatius. A spectacle of breathtaking sunrises and sunsets. Far from the noise and hustle of the city, you will find peace and quiet guaranteed. You will find 5 minutes drive from the villa: beaches, restaurants and all amenities.

May 12 – 19

$873 CAD per night

Guest favourite

Villa in Sint Maarten, Sint Maarten

5.0 out of 5 average rating, 15 reviews

Beachfront/6 bdrs en-suite/Maid included (J)

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.

Aug. 9 – 16

$1,427 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

Aug. 25 – Sep. 1

$378 CAD per night

Superhost

Guest suite in Upper Prince's Quarter, Sint Maarten

4.81 out of 5 average rating, 16 reviews

Sunrise Getaway

Enjoy breathtaking views while being in bed. Located directly by the ocean, this is your peaceful get away! Master bedroom with a queen size bed, and air conditioning. Second bedroom with a queen bed and fan. Both rooms include ceiling fans. Ocean views from all rooms and balcony. Wifi is free and accessible. Fully equipped kitchen with stove, oven, refrigerator (with water dispenser & Ice maker), coffee maker and microwave. All utensils with indoor and outdoor sitting area.

Nov. 16 – 23

$174 CAD per night

Guest favourite

Condo in Maho, Sint Maarten

4.88 out of 5 average rating, 171 reviews

2 Min to Beach/Exclusive Rooftop Jacuzzi, Pool+Bar

This charming, cozy, and tranquil tropical nest is located where all the action is! The golf course, iconic bars, the unprecedented landing strip, the popular Maho and Mullet bay beaches, Maho market with daily fresh take away breakfast/lunch buffets and a divine selection of exotic restaurants are all in walking distance! If you wish to just lounge and relax by the pool, jacuzzi, and private gazebo bar or enjoy the nightlife; it’s all readily available, at your fingertips!

Oct. 12 – 19

$251 CAD per night

Guest favourite

Home in Upper Prince's Quarter, Sint Maarten

5.0 out of 5 average rating, 18 reviews

Peaceful secluded 2BR apt w. sunrise & ocean views

This guesthouse is a hidden gem! The most southern house on the island, secluded and peaceful with breathtaking ocean and sunrise views. It provides ultimate relaxation. Let the ocean breeze refresh your mind, body, soul. The large patio area is perfect to enjoy the gorgeous sunrises. The hiking trail to the natural pools is nearby. Shopping & the port for day trips to St. Barths & Saba is a 5 minute drive away. Rental car is a must as guesthouse is located in the hills.

Aug. 24 – 31

$172 CAD per night

Guest favourite

Loft in Marigot, St. Martin

4.99 out of 5 average rating, 116 reviews

Sea Loft Stunning View - Private Pool

* 200m² Loft * Exceptional sea views * Private pool * 250 meters to small beach Galisbay * Terrace with sun loungers, garden furniture, garden furniture, outdoor table, and BBQ * Desk area * 100 Mbps WiFi * TV with thousands of channels from all over the world * A 250m walk to Marina Fort Louis de Marigot * 5 min walk to the city center of Marigot with its restaurants, shops and other shops * 5 min from the pier for St. Barts and Anguilla, and the taxi station

Apr. 22 – 29

$652 CAD per night

Guest favourite

Apartment in Philipsburg, Sint Maarten

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.

Apr. 10 – 17

$319 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.

Mar. 25 – Apr. 1

$160 CAD per night