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

4.97 out of 5 average rating, 65 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.

19–26 May

$171 SGD 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

$505 SGD 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.

19–26 Apr

$822 SGD 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...

2–9 Jun

$176 SGD per night

Guest favourite

Flat in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 171 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

9–16 Oct

$410 SGD 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!

11–18 Sep

$213 SGD 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

7–14 Sep

$296 SGD per night

Guest favourite

Apartment in Simpson Bay, Sint Maarten

4.97 out of 5 average rating, 35 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.

30 Mar – 6 Apr

$386 SGD per night

Guest favourite

Apartment in Collectivity of Saint Martin, St. Martin

5.0 out of 5 average rating, 63 reviews

Holidays in the Paradise on the Beach

Apartment with magnificent sea views Directly on Nettlé Bay beach with pool Close to shops Restaurant, bakery, pharmacy... 15 minutes from Juliana International Airport and Mullet Bay Golf Plage de Baie rouge et baie aux prunes 10 Minutes Although life on our Friendly island is very good , it is to be noted that electricity and water disruptions may happen please be assured that all concerned do their utmost to minimize any Inconvénience « Thank You 🥰

25 Aug – 1 Sep

$202 SGD 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.

8–15 Aug

$548 SGD 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 area * Wifi 100 Mbps * TV with thousands of channels from around the world * 250m walk to Fort Louis de Marigot Marina * 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

16–23 Jan

$587 SGD per night

Guest favourite

Flat in Philipsburg, Sint Maarten

4.98 out of 5 average rating, 122 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.

12–19 Jun

$235 SGD per night