Family-friendly vacation rentals in Upper Prince's Quarter

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Top-rated family-friendly rentals in Upper Prince's Quarter

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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

$1,298 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

$374 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

$249 CAD per night

Guest favourite

Apartment in Philipsburg, Sint Maarten

4.93 out of 5 average rating, 176 reviews

Blue grand view studio with infinity pool

This is a perfect studio for anyone who wants to enjoy all of SXM. It is close to restaurants, bars, casinos, the city center and the beach(3 minutes walking). The apartment has a full kitchen and a gorgeous terrace. You will love this place because of the ambiance and the outdoors space and of course the infinity pool with breathtaking views of the island overseeing Philipsburgs Great Bay with its cruise ships and Divi Little Bay. Check the reviews :-)

Nov. 28 – Dec. 5

$373 CAD per night

Guest favourite

Apartment in Lowlands, Sint Maarten

4.97 out of 5 average rating, 113 reviews

Cupecoy Côté Jardin

Delightful one bedroom appt. Fully furnished with mid century teak furniture. A spacious 70m2 space with large terrace in a mature tropical garden. A brand new fully equipped kitchen was added in October 2022. Located in trendy and safe Cupecoy. CJ1 is a quiet oasis to relax in the luxurious garden, or head for the the renowned beach of Mullet bay within a 3 minute walk. Supermarkets, gym yoga studio very close by. This is the place to be.

Jul. 5 – 12

$258 CAD per night

Guest favourite

Villa in Saint Barthélemy, St. Barthélemy

4.98 out of 5 average rating, 127 reviews

Villa RIDE

RIDE is a 2017 VILLA located on hilltop of anse des cayes offering a beautiful seaview. 5 min driving from the beach , gustavia ( main city ) , and a delicious bakery store. It offers quiet and privacy while remaining close to everything. The villa can welcome 4 PEOPLE in 2 BEDROOMS, each one having their own private massive wood bathroom . The villa is also accessible to people with REDUCED MOBILITY thanks to its one level access.

Nov. 20 – 27

$1,074 CAD per night

Guest favourite

Condo in Marigot, St. Martin

4.8 out of 5 average rating, 109 reviews

Charming studio directly on the beach

A perfect place for an idyllic relaxing, with its balcony on the sea and the beach at your feet. It comfortably fits two, and it's centrally located at walking distance from all the restaurants, boutiques, supermarkets, and transport services. You'll love it! Conveniently close to the city of Marigot, but far enough from all its noise once in your little nest. You will be 20 minutes or less by car from your desired destination.

Jan. 31 – Feb. 7

$218 CAD per night

Guest favourite

Villa in Upper Princess Quarter, Sint Maarten

5.0 out of 5 average rating, 10 reviews

Luxury Villa Twin Palms

Back by Popular Demand... Villa 'Twin Palms’ offers a unique opportunity to enjoy your own Private & Luxurious Tropical Villa while enjoying breathtaking and endless ocean views. The villa is tucked into the beautiful hillside inside the the secluded ‘Dawn Beach Estates" This villa in a 2 bedroom villa, the 3rd bedroom is available only on request for an additional fee

Mar. 18 – 25

$617 CAD per night

Superhost

Villa in Anse Des Cayes, St. Barthélemy

4.95 out of 5 average rating, 116 reviews

The Perfect Beach House

Villa Palmier is a stunning 2 bedroom, 2 bathroom newly renovated villa in the well located neighborhood of Anse Des Cayes. It is a designers dream having just been featured in the July/August issue of Elle Decor France. With ocean views from every room, a constant sea breeze blowing throughout, and your own private pool, it's the perfect beach retreat.

Aug. 9 – 16

$1,234 CAD per night

Guest favourite

Apartment in Simpson Bay, Sint Maarten

4.82 out of 5 average rating, 151 reviews

Apartment on the beach 2

Beach front apartment with beautiful ocean view and Simpson Bay beach is ready to welcome you! It is located in Simpson Bay, walking distance to the tourist area with many restaurants, bars, clubs, grocery store, spas, night clubs and much more!!! You’ll love my place because of the gorgeous view, the location and the ambiance.

Aug. 8 – 15

$233 CAD per night

Guest favourite

Cottage in Cul-de-Sac, St. Martin

4.98 out of 5 average rating, 101 reviews

VILLA JADE 2: WATERFRONT/ POOL

VILLA JADE is a complex of 3 villas located in THE BAY OF ASS DE SAC and its islets ... VILLA JADE 2 is a spacious suite/sea view for 2 people seafront, with private pool. The 3 villas are adjoining but very quiet and intimate. Your only view is the sea... Direct access to the sea by a pontoon, and kayaks at your disposal.

Oct. 21 – 28

$407 CAD per night

Superhost

Guesthouse in Little Bay, Sint Maarten

4.85 out of 5 average rating, 214 reviews

Great view w/private pool

Long idelness by the infinity pool. Two bedrooms each with its own bathroom and seperate toilette. A few minutes from the beach, shops and nightlife and yet in a quiet and safe area. The guests has the entire home with a private pool. Please check “villa_pi” on instagram for more photos

Mar. 19 – 26

$498 CAD per night