Holiday rentals with a pool in Simpson Bay

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Top-rated rentals with a pool in Simpson Bay

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Apartment in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 56 reviews

Beach front luxury! Huge 2BR that has it all! 😍🤩😍

5 star hotel luxury is yours in this modern beach home! 2 guest rooms with en-suite bathrooms and deck access. Enjoy cooking your own meals and dine inside or on the deck (or beach!). Largest deck on Simpson Bay beach has it all: huge daybed, loungers, living and dining areas for your comfort and pleasure. Unwind in the den and enjoy the big screen there or in either bedroom. Your neighbor is a boutique hotel and will gladly serve you meals and drinks right to your deck! Much more info available

14–21 Jan

$1,363 SGD per night

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

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

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.

20–27 Sep

$224 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

Apartment in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 6 reviews

Renovated 2-Level Condo @ Simpson Bay Yacht Club

This spacious and luxurious 1-bedroom 2-level condo, has been appointed with high-end Miele appliances, granite counters, rain-shower heads in both bathrooms, Stressless leather couches and Posture-pedic beds for your ultimate comfort. The main floor balcony and very private upper balcony offer gorgeous views across the lagoon to nearby marinas and mountains. Your reserved parking is steps from your door in this sought after gated community in the heart of Simpson Bay.

12–19 Aug

$198 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

Home in Calabash Rd, Cole Bay, Sint Maarten

4.93 out of 5 average rating, 110 reviews

THE HILL HOUSE, 2 Bdr, pool, panoramique vue

La maison se compose de 2 belles chambres avec piscine dans le quartier residentiel de Almond Grove Estate, sécurisé 24h/24, (résidence de standing), la villa est entièrement privée, vous ne partagerez pas la piscine et ses extérieurs. Vous allez apprécier le charme de cette maison. La vue est juste magnifique, collines verdoyantes et mer de Simpson bay, un endroit à la fois discret et proche de l agitation touristique, des commerces et des plages.

6–13 Apr

$422 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 Lowlands, Sint Maarten

4.83 out of 5 average rating, 18 reviews

The Emerald at Maho

Welcome to "Hangar 310W" , a unique and cozy condo located in the heart of Maho with views of Princess Julianna International airport. The condo is in walking distance to all the basics you need for your intended stay. Just a 5 minute walk to Maho village which is full of shops, a variety of restaurants, bars, casinos and nightclubs. The world famous Maho Beach is a 10 minute walk where you can smell the jet fuel up close and personal.

21–28 Aug

$123 SGD per night

Guest favourite

Flat in Little Bay, Sint Maarten

4.98 out of 5 average rating, 113 reviews

Stunning 2 BD Ocean View - Terraces Lt Bay

Treat yourself to the utmost stylish and modern ocean view apartment located in the exclusive Little Bay Hill . This spacious environment, is designed to be enjoyed as a family, has a terrace with stunning sea views, private pool, one master suites ( Japanese king bed and a walking closet), one bedroom suite with two twin size beds ( could be converted to king size bed ) . Welcome to Terraces Little Bay !

11–18 Jan

$596 SGD per night