Vacation rentals with a pool in Simpson Bay

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Simpson Bay

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

0 of 0 items showing

1 of 3 pages

Guest favourite

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

Sep. 23 – 30

$868 CAD per night

Guest favourite

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

$531 CAD per night

Guest favourite

Condo in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 14 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. 9 – 16

$424 CAD 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.

May 8 – 15

$870 CAD per night

Guest favourite

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...

Mar. 14 – 21

$232 CAD 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.

May 14 – 21

$237 CAD per night

Guest favourite

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!

Oct. 12 – 19

$250 CAD 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.

Aug. 12 – 19

$231 CAD 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 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. 26 – Feb. 2

$649 CAD per night

Guest favourite

Apartment in Cupecoy, Sint Maarten

5.0 out of 5 average rating, 6 reviews

Bright Studio by Mullet Beach

Bright and charming studio 5 minutes from the airport and just steps from Mullet Bay in a safe, gated community. The apartment features amenities such as night time guarded security, included wifi, TV with Netflix, A/C, Full kitchen, 3 Piece Bathroom, Queen bed, with an outdoor pool , gazebo and grill. Just a 3 minute walk from local restaurants and bars, supermarket, and the AUC medical school. Beach chairs and pool toys are also in the apartment for use.

Jul. 12 – 19

$139 CAD per night

Guest favourite

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. 13 – 20

$410 CAD per night

Guest favourite

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 !

Aug. 25 – Sep. 1

$518 CAD per night