Vacation 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

4.95 out of 5 average rating, 124 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.

Condo in Marigot

Studio «SeaBird» les pieds dans l’eau sur la plage

Le « studio SeaBird » est idéalement situé avec une vue magnifique sur la mer Caraïbes et une plage idyllique rien que pour vous! Il offre beaucoup de confort et de rangement avec une décoration raffinée et originale. La résidence est parfaitement sécurisée avec une grande piscine et jardin tropical. Tout est accessible à pied: épicerie, marché local, boutiques, restaurants traditionnels ou gastronomiques, gare maritime vers les autres îles, etc... Wifi haut débit et télé Europe et Amérique.

5 out of 5 average rating, 53 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.

Apartment 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.

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.

Apartment 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.

Condo 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...

4.99 out of 5 average rating, 169 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 in Marigot

Sea Loft Vue imprenable - piscine privée

* Loft de 200m² * Vue mer exceptionnelle * Piscine privée * A 250 mètres de la petite plage de Galisbay * Terrasse avec chaises longues, salon de jardin, table d'extérieur et BBQ * Espace bureau * Wifi 100 Mbps * TV avec milliers de chaines du monde entier * A 250 m à pied de la marina Fort Louis de Marigot * A 5 min à pied du centre ville de Marigot avec ses restaurants, boutiques et autres commerces * A 5 min de l'embarcadère pour Saint-Barth et Anguilla, et de la station de taxis

4.9 out of 5 average rating, 214 reviews

Condo 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.

Home in Calabash Rd, Cole Bay

4.9 out of 5 average rating, 153 reviews

THE HILL HOUSE, 2 Bdr, pool, panoramique vue

Hébergement avec piscine privée et vue à couper le souffle Offrez-vous une parenthèse de rêve dans cette maison élégante, nichée dans le quartier sécurisé Almond Grove Estate. Profitez de 2 chambres climatisées, d’un salon lumineux, d’une cuisine équipée, et surtout d’un espace extérieur idyllique avec piscine et vue panoramique sur Simpson Bay. À seulement 5 min de Marigot, 10 min de l’aéroport et 15 min des plages, c’est l’adresse parfaite pour un séjour inoubliable !

Apartment in Point Pirouette

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

4.95 out of 5 average rating, 108 reviews

An inviting outdoor space features a private pool surrounded by lush greenery and sea views. Comfortable lounge chairs are positioned nearby, providing a serene spot to relax. Sunlight reflects off the water's surface, creating a tranquil atmosphere.

Apartment in Indigo bay

Appartement indépendant bas de villa - Indigo Bay

L'appartement de la Villa Stella vous accueille dans un cadre unique avec une vue spectaculaire sur la mer des Caraïbes. Située dans une résidence sécurisée 24h/24, la tranquillité est au rendez-vous. Vous serez à seulement 8 min à pied de la plage d'Indigo Bay et proche des commerces et restaurants de la partie néerlandaise. Composée de 2 chambres et de 2 salles de bain, vous pourrez vous détendre dans la piscine/jacuzzi surplombant la baie .

Apartment in Cupecoy Beach

A sleek living space features expansive glass doors that open to a balcony overlooking the beach and ocean. A coffee table displays flutes and a bottle of champagne, while a modern chair and sculptural accent table complement the area. Scenic views of the coastline are visible.

4.84 out of 5 average rating, 38 reviews

A-1002 Incredible 1 bedroom with a balcony

Welcome to Fourteen at Mullet Bay, one of the most exquisite and luxurious beachfront residence in St Maarten located directly on the famous Mullet Bay beach and golf course.<br><br>As you enter this beautiful one bedroom condo apartment that offer up to 85.5 square meter with balcony of fully furnished living space, you will directly feel at ease overlooking the stunning white sandy beach of Mullet Bay and its breathtaking turquoise waters.

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, 19 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 in Cole Bay

Pelican key - BEACH FRONT Villa

5 out of 5 average rating, 41 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

Home in Upper Prince's Quarter

A modern kitchen and living area are visible, featuring a large island with bar seating, complemented by pendant lighting. Floor-to-ceiling glass doors provide access to an outdoor terrace with ocean views. Natural light fills the space, enhancing the contemporary decor.

5 out of 5 average rating, 19 reviews

Aman Oceanview

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

Home in Les Terres Basses

A refreshing pool is framed by a spacious wooden deck, furnished with multiple loungers for relaxation. Lush greenery and palm trees surround the area, creating a private outdoor retreat. The clear blue sky enhances the inviting atmosphere of this tranquil space.

5 out of 5 average rating, 9 reviews

Villa Monchal, 1 minute à pieds de la plage

4.93 out of 5 average rating, 14 reviews

Two lounge chairs are positioned on a wooden deck, facing the turquoise waters. A small table is placed between them, featuring decorative items. In the background, rocky coastline and distant hills are visible under a blue sky adorned with clouds.

Home in Marigot

"Sweet Home on the Beach"

5 out of 5 average rating, 19 reviews

A modern villa exterior features a sleek infinity pool surrounded by a tiled terrace. A spacious dining area is set beneath a pergola, complemented by tropical plants and a distant hillside view. Sunlight reflects off the pool's surface, enhancing the inviting atmosphere.

Home in Sint Maarten

Infinite Blue – Elegant Villa & Turquoise Views

Condo rentals with a pool

Condo in Collectivity of Saint Martin

A spacious terrace offers direct views of sandy beach and gentle waves. Two lounge chairs are positioned for relaxation under a shade. The background features a rocky shoreline and lush mountains, while a clear sky enhances the inviting coastal scenery.

5 out of 5 average rating, 35 reviews

Les pieds dans l'eau, ELBA magnifique ! 2 à 4 Pers

Condo in Saint Martin,Guadeloupe

Two sun loungers are positioned on a sandy beach, accompanied by a small table holding a bottle of champagne and two glasses. A backdrop of clear blue water and gentle waves is visible, with a few green trees enhancing the tranquil setting.

5 out of 5 average rating, 53 reviews

Villa Belharra, amazing view

A serene view of the property’s swimming pool surrounded by lush greenery and palm trees. Loungers are positioned along the poolside, providing spaces for relaxation. The turquoise waters of Simpson Bay are visible in the background, complemented by a clear blue sky.

4.88 out of 5 average rating, 56 reviews

2BR Beachfront Oasis •Pool + Epic Sunsets @Encanto

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!

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

A spacious living area is depicted, featuring a light-colored sectional sofa and two armchairs facing a flat-screen television. Natural light fills the room through large sliding doors that open to a garden view, complemented by tasteful indoor plants and soft furnishings.

4.99 out of 5 average rating, 69 reviews

The Beach Condo

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.

Condo 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.

Condo in Cupecoy

Mullet Bay Suite 802 - Your luxury vacation in SXM

Other vacation rentals with a pool

4.84 out of 5 average rating, 55 reviews

A refreshing outdoor pool is flanked by lounge chairs under shaded umbrellas. Lush greenery surrounds the area, and a covered seating space is visible in the background, providing options for relaxation.

Apartment in Lowlands

B Maho Studio

5 out of 5 average rating, 63 reviews

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.

Apartment in Lowlands

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.

Apartment in Lowlands

Stunning Gem in Prime Location

5 out of 5 average rating, 9 reviews

A spacious terrace is complemented by a dining table surrounded by four chairs. A comfortable seating area with two wooden chairs and a couch is visible. Large glass windows provide a view of the lagoon and the outdoors, enhancing the natural light in the space.

Apartment in Marigot

NEW 1BR apt lagoon & sunset view 2/3p

Villa in Indigo bay, Sint Maarten

A private pool is set in a serene outdoor area, surrounded by lush greenery and palm trees. The pool features a tiled edge, with a wooden tray holding tropical fruits floating in the clear water. A spacious lawn complements the inviting atmosphere.

5 out of 5 average rating, 30 reviews

Ocean Dream Villa

4.93 out of 5 average rating, 55 reviews

A living area features a modern television mounted on a minimalist white console. A circular coffee table sits below, accompanied by a decorative shell. Light filters through sheer curtains, illuminating the space and offering a glimpse of the outdoor area.

Condo in Marigot

Beachfront Condo| Pool View + Private Beach Access

4.98 out of 5 average rating, 89 reviews

A modern living area is showcased, featuring a light gray sofa adorned with colorful cushions. A wooden coffee table is centered on a patterned rug. Large glass doors open to a balcony surrounded by greenery, while a ceiling fan provides air circulation. A wall art piece adds a touch of character.

Condo in Marigot

cosy apartment