Waterfront vacation rentals in Simpson Bay

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Top-rated waterfront rentals in Simpson Bay

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Guest favorite

Condo 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

Dec 16 – 23

$392 per night

Guest favorite

Condo in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 16 reviews

Beachfront Caribbean Breeze in Paradise, SXM

Caribbean Breeze inviting Beach front home. A few steps to our beach and pool. Walk to main stream. Amazing views . 2/2.5 with huge Master. Hear the waves flowing in onto the shore for those relaxing days and nights. New kitchen, living room area, bathrooms, dinning area with a Caribbean feel. Unwind on any balcony, penthouse ocean view, on daybed with a nice drink , looking over the verse tranquil ocean. Take a dip in the soothing crystal clear waters. Amenities enclosed & Wi-Fi included.

Sep 5 – 12

$248 per night

Guest favorite

Apartment in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 26 reviews

Le Papillon -Modern, beachfront, 550sq. ft terrace

Le Papillon enjoys one of the best locations on St. Martin, with many wonderful restaurants nearby and a beach that is close to private and ideal for long walks. Overlooking the entire Simpson Bay beach, the comfortable 2150 sq. feet apartment is equipped with everything a visitor might need. The long list of our luxurious amenities is shown below. The terrace itself is so comfortable and large that many guests mentioned that they would not mind living there. The view is breathtaking.

Aug 1 – 8

$390 per night

Guest favorite

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.

Nov 5 – 12

$525 per night

Guest favorite

Apartment in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 12 reviews

Comfy Beachside Vacation I

Located in Beacon Hill within the Simpson Bay district, this unit has a 1-bedroom apartment with 2 double beds that welcomes a max of 4 guests. The stunning view of its private beach is nearly a few steps away from the location. You can also catch the closest view of our island's most famous attraction airplane landings and takeoffs adjacent to the main airport! Nightly entertainments such as casinos, nightclubs, and restaurants are a 2 minutes drive (12mins walking) from the location.

Jul 26 – Aug 2

$110 per night

Guest favorite

Condo in Lowlands, Sint Maarten

4.94 out of 5 average rating, 89 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...

Jun 12 – 19

$112 per night

Guest favorite

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

Oct 13 – 20

$271 per night

Superhost

Apartment 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.

Aug 14 – 21

$143 per night

Superhost

Apartment 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

Sep 19 – 26

$181 per night

Guest favorite

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!

Aug 26 – Sep 2

$136 per night

Guest favorite

Loft in Marigot, St. Martin

4.99 out of 5 average rating, 118 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

Jan 1 – 8

$499 per night

Guest favorite

Condo 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.

Oct 30 – Nov 6

$350 per night