Holiday rentals with a pool in Simpson Bay

A spacious daybed is shaded by a wooden pergola, surrounded by vibrant greenery. The beach and ocean serve as a backdrop, with gentle waves lapping at the shore. Colorful cushions and a soft blanket add comfort, while a small Buddha statue creates a serene ambiance.

4.97 out of 5 average rating, 91 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

A cozy living area features a comfortable gray sofa and a wooden coffee table. Two windows offer expansive views of the ocean, with light reflecting off the water. Beams stretch across the ceiling, enhancing the airy feel of the space.

4.8 out of 5 average rating, 174 reviews

Oceanfront w Pool | Maho Beach area

Location , Location Location ! You can not get any closer to the ocean than in this cliff side apartment. The sound of waves crashing below and incredible ocean views from every room. The sunrise is magical everyday and by night the glowing lights of Simpson bay. This cliff side apartment has everything you need for a dream stay away from the crowds. . Just steps from 4 beaches Simpson bay, Mullet bay, burgeux bay and a 5minute walk to the world famous Maho Beach with its famous plane landings

5 out of 5 average rating, 55 reviews

A bright living area features large glass doors that open to a private outdoor space. A comfortable sofa and a coffee table are positioned on a light-toned rug. A TV is mounted on a sleek white cabinet, while wooden accents add warmth to the design.

Flat in Simpson Bay

The Loft at Simpson Bay Yacht Club

Welcome to The Loft at SBYC. 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. Free concierge service included.

A slender palm tree leans towards the shore, where vibrant turquoise waters meet a soft sandy beach. A white picket fence runs along the beachfront, providing a clear view of the tranquil ocean and distant coastline under a bright blue sky.

5 out of 5 average rating, 30 reviews

Beachfront Caribbean Breeze in Paradise, SXM

Caribbean Breeze inviting Beach front home. A few steps to our beach and pool. Walk to mainstream. 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 , bathrooms, dining area,etc. 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, 1 minute walk away. Amenities enclosed & Wi-Fi included.

4.97 out of 5 average rating, 39 reviews

A private outdoor area features a crystal-clear pool surrounded by sun loungers. A gazebo is visible to one side, providing shaded space. The vibrant yellow and natural stone walls enhance the inviting atmosphere, while palm trees contribute to the tropical feel, all under a clear blue sky.

Flat in Simpson Bay

Private Pool- 5 min DRIVE to Maho Beach & Airport

OUTDOOR AREA (NOT shared with other guests) - Automatic Generator - Private Pool - Private Gazebo - chairs and table - Beach Towels - Grill ONE BEDROOM - Queen Size Bed - Smart Samsung TV - High speed WIFI - Storage spaces - Air conditioning LIVING ROOM - Dinning table for two - A Sofa BATHROOM - Walk-In Shower with HOT water - Essential Toiletries provided KITCHEN - Coffee Maker - Stove/ Oven (Gas) - Fridge/ Freezer - Washer/Dryer - kitchen appliances - Coffee and tea

4.95 out of 5 average rating, 123 reviews

A scenic view reveals a large swimming pool surrounded by lounge chairs and colorful flower gardens. The sparkling blue ocean and a distant boat can be seen, under a bright sky with fluffy clouds. Palm trees gently sway in the breeze, adding to the tropical ambiance.

Apartment in Lowlands

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...

4.96 out of 5 average rating, 28 reviews

An aerial view captures the vibrant landscape of Simpson Bay Yacht Club, revealing the layout of the community, including palm trees, two swimming pools, and tennis courts. The calm turquoise waters border the marina, and the lush green hills rise in the background, complementing the scene.

Flat in Simpson Bay

The Pineapple Suite

Discover The Pineapple Suite, a chic 2-bedroom retreat accommodating up to 4 guests, nestled within the secure confines of Simpson Bay Yacht Club's gated community. Unwind in modern luxury, relish on-site amenities like the two swimming pools, tennis courts, bbq area and soak in breathtaking views of the yachts, lagoon, hills and sunset from your balcony. Conveniently located near the airport in Simpson Bay within walking distance from restaurants, the beach, bars and supermarkets.

4.9 out of 5 average rating, 214 reviews

Apartment in Maho

Maho Love Nest: Unwind by the Rooftop Pool&Hot Tub

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 for you to indulge.

4.96 out of 5 average rating, 75 reviews

Villa in Simpson Bay

Waterfront "Bonjour" Beacon Hill St Maarten

This stunning 4-bedrooms, 4 bathrooms villa overlooks Maho Bay and provides a front row seat to beautiful SXM sunsets, and over the famous Maho Beach. Enjoy the views while taking a dip in the home’s infinity pool overlooking the ocean or from its multiple outdoor dining and seating options conveniently and securely located minutes from restaurants, bars, nightlife, Maho Market and more, steps away from direct beach access to Simpson Bay Beach. Back up Diesel Generator

4.9 out of 5 average rating, 63 reviews

A modern villa exterior is displayed under a clear blue sky. Sleek white walls are complemented by well-maintained landscaping and palm trees. An outdoor lounge area is visible, featuring comfortable seating and a shaded area for relaxation.

Villa in Simpson Bay

Modern 2 bedroom luxury beachside villa with pool

Your own private paradise. Modern 2 bedroom luxury villa in safe gated community with security. New appliances with air conditioning, WIFI, security cameras, and secured free parking including Smart TV with free NetFlix, HBO Max, and Prime access. Private pool with adjacent outdoor dining/lounge area. Perfect for families or couples. Maid and private chef service available if needed. Walking distance from dining, night clubs, and shopping. Steps away from the beach.

A bright living area features large glass doors opening to a waterfront view. Neutral-toned furnishings include a comfortable sofa and a unique wooden coffee table atop a circular area rug. Decorative greenery and modern art elements provide subtle accents against the white walls.

4.91 out of 5 average rating, 121 reviews

Secret View amazing apartment- Private pool

Welcome to Secret View, a stunning, fully renovated, stylish and modern apartment located directly on the lagoon with a private pool and breathtaking views. Quiet and secure area, next by Maho, Mullet Bay, the golf course, supermarket, bars, restaurants, and casinos. A true sanctuary, it’s sure to be the highlight of your holiday. Private and free parking Your ultimate vacation retreat. Sint Maarten is currently experiencing some daily power outages

4.99 out of 5 average rating, 170 reviews

An outdoor terrace features comfortable white lounge furniture arranged around a coffee table. Sun loungers are positioned beside a private infinity pool, overlooking the ocean and distant boats. The scene is framed by tropical plants and a clear blue sky, enhancing the serene coastal environment.

Loft

Sea Loft, Breathtaking View – Private Pool

* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with deckchairs, garden furniture, outdoor table and BBQ * Office space * 100 Mbps WiFi * TV with thousands of channels from around the world * 250 m walk to Fort Louis de Marigot marina * 5 min walk to Marigot city center with its restaurants, shops and other stores * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

Popular amenities for Simpson Bay rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 20 reviews

An infinity pool reflects the bright blue sky and shimmering sea, creating a tranquil contrast. The edges of the pool are lined with clear glass panels, providing unobstructed views of the horizon. The sunlight sparkles on the water's surface, emphasizing the serene setting.

Home in Indigo Bay

Life's Good

5 out of 5 average rating, 20 reviews

Steps leading down to a sandy beach are framed by a white railing. The clear turquoise water laps gently at the shore, revealing a mix of sand and smooth stones. Bright sunlight illuminates the tranquil scene, highlighting the serene coastal atmosphere.

Home

Pelican key - BEACH FRONT Villa

5 out of 5 average rating, 42 reviews

An outdoor dining area is set for a meal with an expansive table that accommodates eight or more guests. The space features sleek chairs and offers unobstructed views of the ocean and horizon, framed by clear skies. The surrounding area reflects a serene coastal ambiance.

Home in Sint Maarten

Ocean View Villa-Indigo Bay W/Private Pool/0 Steps

5 out of 5 average rating, 26 reviews

A modern pool area is positioned by the ocean, featuring a clear blue water pool and two sun loungers. A potted palm adds a tropical touch, with the horizon visible beyond gentle waves and scattered clouds.

Home in Cole Bay

New-Sunset Place Villa w Stunning Waterfront Views

Home in Les Terres Basses

A private terrace is framed by lush greenery, showcasing a sleek infinity pool with a stone edge. Two lounge chairs are positioned nearby, complemented by a small seating area. A modern entrance leads to the interior space, under a bright blue sky with scattered clouds.

4.96 out of 5 average rating, 68 reviews

Luxurious bungalow with private pool

5 out of 5 average rating, 6 reviews

An expansive infinity pool extends toward scenic ocean views, framed by gentle hills. Several lounge chairs line the pool area, inviting relaxation. The tranquil bay is dotted with boats, while the horizon features a backdrop of distant islands under a partly cloudy sky.

Home in Pelican

Luxurious villa with magnificent view ALSO 6bedr!

4.83 out of 5 average rating, 189 reviews

An inviting infinity pool stretches toward the horizon, offering uninterrupted views of the ocean and coastline. A covered terrace with two lounge chairs is positioned nearby, framed by a modern architectural structure that enhances the surrounding scenic beauty.

Home in Indigo Bay

Préstige - Luxurious 3 bedroom by the Beach

Home in Upper Prince's Quarter

An outdoor lounge area features a modern pergola with plush seating and neatly arranged towels. The infinity pool, with its seamless edge, reflects the vibrant blue of the ocean under a clear sky, providing expansive views of the coastline and surrounding landscape.

4.96 out of 5 average rating, 53 reviews

Teresa’s Ocean Paradise

Apartment rentals with a pool

4.95 out of 5 average rating, 125 reviews

A serene beachfront view is presented through sliding glass doors, showcasing a private terrace with a small round table and two chairs. Palm trees gently sway in the breeze, framing the clear turquoise sea and sandy beach beyond.

Apartment in Marigot

"SeaBird" studio, feet in the water on the beach

A landscape scene captures a serene beachfront view featuring soft, white sand and clear turquoise waters. Lush palm trees are seen in the foreground, while a large infinity pool reflects the sky. The horizon showcases gentle waves against the backdrop of a clear blue sky.

5 out of 5 average rating, 5 reviews

Paradiso - 2 bedroom Condo steps to Cupecoy Beach!

5 out of 5 average rating, 30 reviews

A balcony is presented with two yellow chairs and a small table, set against a backdrop of a sparkling blue sea dotted with sailboats. Lush green plants add a touch of nature, and a clear blue sky creates a bright and open atmosphere.

Apartment in Marigot

New studio with superb view of the Caribbean Sea

A spacious bedroom features a large window offering panoramic views of the ocean and nearby mountains. Two elegant chairs sit beside a small table, with a tray holding beverages and snacks placed on the bed. Natural light fills the room, creating a bright atmosphere.

4.91 out of 5 average rating, 22 reviews

Beacon Hill Hideaway: Luxury Condo in Simpson Bay

4.83 out of 5 average rating, 122 reviews

A living area is presented with a wooden cabinet housing a flat-screen TV. Two chairs with woven detailing complement a decorative potted palm. The light and airy space is accented by white walls and a beamed ceiling, enhancing a serene atmosphere.

Apartment in SX

Large 2BR Condo - STEPS FROM BEACH!

5 out of 5 average rating, 10 reviews

A spacious living area features floor-to-ceiling windows, allowing natural light to fill the space. Stylish blue chairs are arranged around a contemporary coffee table. A large piece of wall art adds a vibrant touch, and modern entertainment equipment can be seen in the background.

Apartment

Mullet Bay Suite 802 - Your luxury vacation in SXM

A tranquil swimming pool is surrounded by lush palm trees and vibrant greenery, reflecting a clear blue sky. The marina, filled with docked yachts, creates a serene backdrop, while lounge chairs are positioned beside the water for relaxation.

4.95 out of 5 average rating, 56 reviews

Studio on the water in the Simpson Bay Yacht Club

4.95 out of 5 average rating, 40 reviews

An outdoor seating area is surrounded by lush palm trees, offering views of the beach. A wooden table is set with pastries and drinks, accompanied by modern grey chairs and sun loungers. The sandy beach is visible in the background under a clear blue sky.

Apartment

Villa Moorea on the beach, sea view 2/4 P.

Other holiday rentals with a pool

The living area features floor-to-ceiling windows offering panoramic views of the lagoon and mountains. A comfortable blue sofa is complemented by textured cushions, with a cozy brown armchair nearby. A round table sits in the center, showcasing a remote control and decorative elements.

5 out of 5 average rating, 64 reviews

Gorgeous 2 bedroom-17th floor, Fourteen Mullet Bay

4.88 out of 5 average rating, 26 reviews

A bright living area features large windows that allow natural light to fill the space, offering views of the outdoors. A comfortable gray sofa is positioned near a round dining table with four chairs. Decorative elements, including a small centerpiece and a television, complete the inviting setting.

Flat in Lowlands

Stunning Gem in Prime Location

Townhouse in Billy Folly Hill

An outdoor seating area offers a spacious table and comfortable couch, framed by a wooden pergola. Views of the ocean and sailboats are visible in the distance, while tropical plants add a natural touch to the relaxed atmosphere.

4.94 out of 5 average rating, 83 reviews

Pelican Sea View 1bdrm Maison Mazu

5 out of 5 average rating, 32 reviews

An infinity pool with crystal-clear water extends alongside the terrace, offering views of the lagoon and surrounding landscape. Palm trees and sun loungers can be seen at the water's edge, with blue skies and fluffy clouds reflecting on the water's surface.

Villa

Brand new! - Slowlife - Enjoy Villa

4.97 out of 5 average rating, 76 reviews

A well-maintained outdoor pool is surrounded by lounge chairs, offering a relaxing space for guests. Shade is provided by large umbrellas, and tropical palm trees are visible in the background. The pool area is complemented by modern residential buildings, enhancing the serene environment.

Apartment in Lowlands

Brand New- Maho Condo Studio with Seaview and Pool

An oceanfront view is presented through floor-to-ceiling windows, revealing a serene seascape. The light-filled space features cozy furnishings in a light palette, emphasizing relaxation. The coastal scenery can be seen from various angles, enhancing the connection to the surrounding environment.

4.97 out of 5 average rating, 31 reviews

CondoSTmaarten panoramic (Adults Only)

A private terrace offers views of the Caribbean Sea and sandy beach, framed by palm trees swaying gently in the breeze. Lounge chairs are positioned to enjoy the tranquil scenery, inviting relaxation under a clear blue sky.

4.93 out of 5 average rating, 42 reviews

Dream Caribbean on the water

A cozy living area features a light gray sectional sofa adorned with striped cushions. Above, a lofted sleeping area is visible. The space is complemented by modern barstools at a wooden counter and framed artwork on the walls, creating a stylish and inviting environment.