Waterfront holiday rentals in Simpson Bay

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Top-rated waterfront rentals in Simpson Bay

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Guest favourite

Place to stay in Sint Maarten, Sint Maarten

4.95 out of 5 average rating, 66 reviews

109/Nite Special Ends Soon Book dates through July

NOTE=THIS IS A "STUDIO" CONDO, NOT A 1 BEDROOM, IN THE MOST HAPPENING SPOT ON THE ISLAND!!! BANG FOR YOUR BUCK!!! MANY PERKS!!! INTERESTED IN PURCHASING A PROPERTY IN ST. MAARTEN, I AM ALSO A REALTOR & I WILL BE HAPPY TO HELP WITH THAT!! Cable TV channels, NETFLIX SMART TV, Movie library, Binoculars, snorkel gear, Boogie Boards & More!! 2 guests Max. NO AUTO BOOKS FOR MORE THAN 2 PEOPLE, OR STAYS LONGER THAN one MONTH. YOU MUST CONTACT OWNER 1ST. CONTACT OWNER FOR BOOKINGS BEYOND ONE YEAR OUT.

2–9 Jul

€ 128 per night

Guest favourite

Apartment in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 29 reviews

Encanto -2BR beachfront w/pool & gorgeous sunsets!

Escape to paradise in this stunning 2-bed 2 bath beachfront condo at Simpson Bay, Sint Maarten. Wake up to the soothing ocean sounds, savor drinks on the patio with uninterrupted turquoise views as you enjoy the privacy of your seaside sanctuary. Immerse yourself in white sandy beaches with direct access to Simpson bay beach. Indulge in nearby restaurants and vibrant nightlife with a 5 min stroll to Simpson Bay Strip. Your coastal sanctuary beckons with unforgettable moments of tranquility

21–28 Nov

€ 363 per night

Guest favourite

Villa in Cul-de-Sac, St. Martin

4.99 out of 5 average rating, 116 reviews

VILLA JADE 1: WATERFRONT SUITE/ POOL

VILLA JADE est située dans la baie de "FRENCH CUL DE SAC". C'est un complexe en bord de mer composé de 3 villas privées. VILLA JADE 1 est une suite pour 2 personnes avec piscine privée. Les villas sont calmes et intimes...votre unique vue est la mer. La baie de "FRENCH CUL DE SAC" est à 5 minutes de ORIENT BAY, touristique avec restaurants, bars, activités nautiques, mais aussi à quelques minutes de GRAND CASE, notre petit village typique avec restaurants gastronomiques en bord de mer....

12–19 Aug

€ 274 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.

11–18 May

€ 594 per night

Guest favourite

Apartment in Lowlands, Sint Maarten

4.94 out of 5 average rating, 88 reviews

Sint Maarten La Terrasse Maho

It's a cozy large studio with a king size bed, a queen size sleeper sofa and a big balcony, it is at the second floor at Royal Islander Club Resort La Terrasse in Maho, fully equipped and furnished. Located just in front of Maho Bay beach and few minutes walk from Mullet bay beach. There are few restaurants and boutiques like cigar shops, jewelers and beauty store. Casino Royale is right next door. There are also a supermarket for grocery shopping, a pharmacy, a clinic and more...

25 Apr – 2 May

€ 135 per night

Guest favourite

Flat 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

28 Apr – 5 May

€ 307 per night

Superhost

Flat in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 3 reviews

The Loft at Simpson Bay Yacht Club

Welcome to The Loft at the Simpson Bay Yacht Club. Located in the heart of Simpson Bay in walking distance to the beach, great restaurants, grocery stores, shopping, salons/spas and more. In this fully renovated loft-style apartment, you will find high quality amenities throughout including a European kitchen and an amazing rainfall shower. The SBYC property offers 3 swimming pools, a hot tub, tennis courts and plenty of outdoor space for relaxing, all under 24-hour gated security.

14–21 Aug

€ 162 per night

Superhost

Flat in Simpson Bay, Sint Maarten

4.93 out of 5 average rating, 100 reviews

Le Petit Paradis - Beachfront 1 Bedroom Apartment

"Petit Paradis" (Little Paradise), a genuine Caribbean getaway. A spacious one-bedroom Beachfront apartment right on beautiful Simpson Bay Beach and in the center of all the happenings. Relaxing terrace, five stairs away from the Beach, and within walking distance from great Restaurants, Nightlife, Activities, and Watersports. This modern, fully furnished, and equipped apartment has everything you need for a dream vacation, Hope to invite you soon in our Paradise, Elodie

18–25 Mar

€ 222 per night

Guest favourite

Apartment 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!

26 Jun – 3 Jul

€ 171 per night

Guest favourite

Apartment in Simpson Bay, Sint Maarten

4.97 out of 5 average rating, 36 reviews

Hamaka condo, a beachfront retreat on Simpson Bay

Escape to the ultimate beachfront retreat at Hamaka, a fully equipped condo recently renovated to offer the perfect private beach escape with easy walking distance access to restaurants, bars, and nightly entertainment in Simpson Bay, Saint-Martin. Experience waking up to the sound of the waves and having your morning drink to the sight of the endless shades of the ocean. At the end of your day, unwind and enjoy the magnificent sunsets that this beautiful island has to offer.

20–27 Mar

€ 291 per night

Guest favourite

Apartment in Simpson Bay, Sint Maarten

4.94 out of 5 average rating, 18 reviews

Beachside Escape

Enjoy our beautiful ocean front condo that is only steps to the lovely Simpson Bay Beach. Relax on the private terrace or roof top patio where you can listen to the waves and watch the sunset! Two bedrooms and 2 full bathrooms give you plenty of room to spread out with family or friends. Centrally located and easy walk to Maho Beach and Center (10–15 minutes) and easy drive (10 minutes) to Mullet Bay Beach and Simpson Bay restaurants and nightlife.

27 Oct – 3 Nov

€ 396 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 view * Private pool * 250 meters from the small beach of Galisbay * Terrace with sun loungers, garden furniture, outdoor table and BBQ * Office space * 100Mbps Wifi * TV with thousands of channels from around the world * 250m walk from Fort Louis de Marigot Marina * 5 min walk to downtown Marigot with restaurants, shops and other shops * 5 min to the pier for Saint-Barth and Anguilla, and taxi station

28 Nov – 5 Dec

€ 439 per night