Vacation rentals with a pool in Simpson Bay

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Top-rated rentals with a pool in Simpson Bay

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Guest favorite

Condo 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

Aug 9 – 16

ﺩ.ﺇ2,395 per night

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

Nov 21 – 28

ﺩ.ﺇ1,389 per night

Guest favorite

Condo in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 51 reviews

The Beach Condo

The Beach Condo, located in Palm Beach Apt. complex is a completely newly renovated 2 bedroom condo right on Simpson Bay Beach. Equipped with all amenities, this is your ideal tropical luxurious getaway. A brand new, fully equipped kitchen, large living and dining area and two king size bed-bedrooms with individual bathrooms give you all the space you need for a retreat in the Caribbean. Lounge on the porch, swim in the pool or live it up on the beach, it's all right there for you to enjoy.

Aug 24 – 31

ﺩ.ﺇ974 per night

Guest favorite

Condo in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 13 reviews

Popular Beachfront Property Barefoot /Simpson bay

This Beautiful Beachfront condo in Sint Maarten, Barefoot, is like being on your own little island. 1 min. to shore. The beautiful crystal blue ocean waters you can see and hear from every corner of this condo. This Oasis has such beauty. Mostly private, quiet and pure tranquility. A constant breeze as you open up the doors and windows to let the sea air open up your senses. 8 minutes from the Dutch airport 16 minutes walking distance from main restaurants casinos and live entertainment.

Oct 11 – 18

ﺩ.ﺇ1,533 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.

May 8 – 15

ﺩ.ﺇ2,261 per night

Guest favorite

Condo 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...

Aug 6 – 13

ﺩ.ﺇ374 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

ﺩ.ﺇ616 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!

Nov 30 – Dec 7

ﺩ.ﺇ713 per night

Superhost

Condo 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.

Oct 14 – 21

ﺩ.ﺇ547 per night

Guest favorite

Home in Calabash Rd, Cole Bay, Sint Maarten

4.93 out of 5 average rating, 111 reviews

THE HILL HOUSE, 2 Bdr, pool, panoramic view

The house consists of 2 beautiful bedrooms with pool in the residential area of Almond Grove Estate, secured 24 hours a day, (luxury residence), the villa is completely private, you will not share the pool and its yard. You will appreciate the charm of this house. The view is just magnificent, green hills and sea of Simpson Bay, a place both discreet and close to tourist hustle and bustle, shopping and beaches.

Sep 15 – 22

ﺩ.ﺇ1,113 per night

Guest favorite

Apartment 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 !

Jan 19 – 26

ﺩ.ﺇ1,642 per night

Guest favorite

Villa in Philipsburg, Sint Maarten

4.99 out of 5 average rating, 224 reviews

Villa Dream View Belair Sint Maarten SXM

Embrace the tranquility in a friendly tropical caribbean modern designed private villa with spacious rooms that are sure to keep you comfortable and feeling at home. Enjoy the sunny day with infinity pool overlooking caribbean sea or enjoy the sea view while watching the sailing huge cruise ships.

Mar 30 – Apr 6

ﺩ.ﺇ2,407 per night