Holiday rentals with a pool in Cole Bay

Home in Upper Prince's Quarter

A spacious bedroom is showcased with a large bed featuring neutral-toned linens. A panoramic window offers stunning views of the ocean and coastline, framed by soft drapes. A bedside table holds a lamp, and a television is positioned across the room, enhancing the modern decor.

Endless Views @ Acqua Bleu

Nestled in the heart of Saint Martin, Acqua Bleu offers breathtaking views of turquoise waters and pristine beaches. You'll have direct access to some of the most gorgeous spots on the island, ensuring endless fun in the sun. You’ll enjoy access to various amenities, including a fully equipped kitchen, spacious living areas, a refreshing swimming pool, and much more! Acqua Bleu features two king bedrooms, each accompanied by a private bathroom. Get ready to enjoy a truly rejuvenating vacation!

4.99 out of 5 average rating, 108 reviews

5.0 out of 5 average rating, 85 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.

5.0 out of 5 average rating, 27 reviews

Apartment in Pelican

Luxurious Hidden Pearl - Private Pool

This luxurious studio has been remodeled in 2025 and is ready for guests seeking a stylish studio with pool. The room has a brand-new kitchen and bathroom and has everything you might need during your vacation. Enjoy the private saltwater pool and relax on the deck on the lounge chairs and comfortable seating areas. The outdoor space is beautifully set up and we offer a BBQ if you like a home cooked meal. The gorgeous tropical garden and breathtaking ocean views complete the experience.

4.81 out of 5 average rating, 103 reviews

A master bedroom featuring large windows that offer a view of the ocean and sky. Natural light floods the spacious area, highlighting the white bedding on the bed and the elegant design of the room. A modern freestanding bathtub is seen in the corner.

Condo in Philipsburg

Horizon (Apt3) – Sea & Pool View, Terrace

Stylish triplex with 3 bedrooms, all with sea and pool view. Located in Black Palm, an elegant residence of 7 apartments in Indigo Bay, a calm and exclusive neighborhood. Indigo Beach is just a 5-minute walk away. Enjoy the shared pool with sea view. Ideal for up to 5 guests: couples, friends or families looking for relaxation. - 5 minutes’ walk from Indigo Beach - 5 minutes’ drive from the nearest supermarket - Private parking on site - Concierge service available for any request.

5.0 out of 5 average rating, 202 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

Condo in Upper Prince's Quarter

Serenity Seascape | 2BR Retreat, 270° Oceanviews

Wake up to a jaw-dropping panoramic view of the Caribbean Sea from this chic oceanfront gem in Point Blanche! Bask in 270° views, picture-perfect sunrises, and views of St. Barths from your own private terrace. The space features modern coastal interiors and hotel-quality bathrooms, blending luxury with cliffside serenity. Located just five minutes from Philipsburg, it offers easy access to beaches, restaurants, and shopping while preserving tranquility.

5.0 out of 5 average rating, 11 reviews

4.98 out of 5 average rating, 40 reviews

A modern living area features large floor-to-ceiling windows that offer panoramic views of the ocean and beach. A light-colored sofa is positioned beside a small wooden table, while a plant adds a touch of greenery. Natural light brightens the space, creating an inviting ambiance.

Apartment in Cupecoy

Stunning oceanfront condo

Unit 1201 in Tower A: Enjoy spacious luxury accommodations for the whole family at this stylish place only minutes from the airport and steps from the famous Mullet Bay Beach. Two spacious bedrooms each with ocean views and 2.5 bathrooms. Take advantage of the fully furnished well appointed kitchen, free gym and free large heated pool with its own restaurant/bar. Stunning panoramic views of the ocean, beach, mountains, and the golf course.

4.99 out of 5 average rating, 189 reviews

A private heated pool is featured at the edge of the terrace, offering views of the ocean and nearby islands. The clear blue water contrasts with the light-colored stone surrounding the pool, while lush greenery can be seen in the background against a clear sky.

Apartment in Little Bay

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 !

4.93 out of 5 average rating, 67 reviews

A panoramic view of the azure ocean is captured, dotted with sailboats. The sandy beach features thatched umbrellas and lounge chairs. Lush palm trees are visible, alongside a beachside bar area with shaded seating, all under a bright sky with fluffy clouds.

Apartment in Simpson Bay

Royal Palm Hilton SXM

This beautiful 2-bedroom 2-bathroom condo is in the heart of Simpson Bay, located inside the Royal Palm Hilton Vacation Club, and offers full resort amenities including a swimming pool, direct beach access, and a gym. This fourth-floor units has dazzling sunset views. Wake up to the beautiful view and then head downstairs where all you have to do is choose between the beach or the pool.

4.83 out of 5 average rating, 215 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

Nestled on the hills of Indigo Bay, Préstige is located midway between Philipsburg and the Simpson Bay touristic hangout. Préstige exudes relaxation the minute you walk through the door, elegant and distinguished! The 3-bedroom spacious residence sleeps six! Overlooking Indigo Beach with private swimming pool! Caribbean living, yours to enjoy!

4.7 out of 5 average rating, 46 reviews

A sleek, reflective pool extends towards the horizon, capturing the vibrant sunset. Lush greenery frames the view, adding a natural element to the scene. The setting creates a peaceful ambiance, inviting relaxation amidst the beauty of the surrounding landscape.

Villa in Cole Bay

A heavenly Sint Maarten's retreat

Perched on a hillside promontory high above St. Maarten, our villa offers breathtaking panoramic views and a central location—ideal for exploring the island’s many treasures. Whether you’re seeking serene mornings by the pool, vibrant beach life, or culinary adventures, this home provides the perfect base for your Caribbean escape.

5.0 out of 5 average rating, 61 reviews

Home in Cole Bay

Spacious 3BR with Private Cozy Pool

This spacious 3-bedroom, 2.5-bathroom home with its own private pool is the perfect retreat for those seeking a luxurious yet cozy getaway. The home is centrally located Cole Bay. It sleeps up to 6 guests and features a private backyard, a fully equipped kitchen and a short drive to beaches, restaurants and supermarkets.

Popular amenities for Cole Bay rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 100 reviews

A tranquil pool reflects the azure sky and distant boats. Surrounded by lush greenery, the pool area features a cascading waterfall and is bordered by smooth stones. A wooden partition provides privacy, enhancing the serene atmosphere of the waterfront retreat.

Home

ALMOND BLUE ...Pinel bay view - caribbean feeling

4.88 out of 5 average rating, 41 reviews

A bright living area features a spacious sofa with light-colored pillows, positioned opposite a wall-mounted television. Two circular coffee tables are placed on a natural fiber rug. A modern lamp and wooden chair add texture, while indoor plants bring a touch of greenery.

Home in Cole Bay

Designer 3BR House w Pool, Sunsets & Ocean Views

5.0 out of 5 average rating, 8 reviews

Home in BAIE NETTLE

Sweet Home on the Beach rdc

5.0 out of 5 average rating, 48 reviews

Home in Philipsburg

Stunning Panoramic Views Of The Ocean & St Barth!

4.97 out of 5 average rating, 38 reviews

Home in Indigo Bay

SeaRenity Villa With Private Pool Indigo Bay

Home in Upper Prince's Quarter

An open-plan living area showcases a modern kitchen with a marble countertop and sleek cabinetry. Large glass doors provide expansive ocean views and access to an outdoor terrace. A comfortable seating area includes neutral-toned furnishings, while dining space is set for meals with panoramic vistas.

Sunrise Over St. Barths

4.98 out of 5 average rating, 47 reviews

5.0 out of 5 average rating, 5 reviews

Home in Indigo Bay

Indigo Bay Condo Shamrock 2 Bed 2 Bath Ocean Views

4.99 out of 5 average rating, 75 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

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

Condo rentals with a pool

4.96 out of 5 average rating, 155 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

4.96 out of 5 average rating, 109 reviews

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.

Condo in Simpson Bay

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

4.98 out of 5 average rating, 120 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.

Condo in Lowlands

Brand New- Maho Condo Studio with Seaview and Pool

4.91 out of 5 average rating, 259 reviews

Condo in Maho

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

4.97 out of 5 average rating, 111 reviews

Condo in Marigot

cosy apartment

4.81 out of 5 average rating, 139 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

Large 2BR Condo - STEPS FROM BEACH!

4.92 out of 5 average rating, 120 reviews

Condo

Sea view, Anse Marcel

4.9 out of 5 average rating, 132 reviews

A serene pool area is surrounded by neatly trimmed grass and tropical plants. Several lounge chairs are positioned around the water, offering relaxation space. Shade is provided by umbrellas, while a view of distant buildings and a waterway is visible in the background under soft evening light.

Condo in Lowlands

Havya Cozy Stays | In Maho, Near Beaches & Airport

Other holiday rentals with a pool

Apartment in Upper Prince's Quarter

Aman_Sky

5.0 out of 5 average rating, 36 reviews

4.83 out of 5 average rating, 18 reviews

Villa in Indigo Bay

AZUR 4BR 4.5BA Walk to Indigo Beach- Sea Side Dr.

4.95 out of 5 average rating, 81 reviews

A private pool is bordered by a spacious patio area, featuring two lounge chairs. Expansive ocean views are visible in the background, with lush greenery surrounding the space. A dining table is situated under a covered area, providing a shaded option for meals outdoors.

Villa in Indigo Bay

Villa Ocean - Indulge Yourself in Paradise

5.0 out of 5 average rating, 5 reviews

Apartment in Cole Bay

Beautiful 3 bedroom condo with a private pool

Luxe

An inviting infinity pool reflects the clear blue sky and ocean, creating a seamless horizon. A floating tray with refreshments is positioned in the water, while a contemporary chair is seen at the pool's edge, enhancing the tranquil atmosphere.

Villa

Ocean Breeze B

5.0 out of 5 average rating, 16 reviews

Villa in Upper Prince's Quarter

Villa Blue Roc

4.94 out of 5 average rating, 88 reviews

4.95 out of 5 average rating, 22 reviews

A spacious living area is characterized by arched doorways allowing natural light to fill the room. A round dining table sits centered, with white chairs and a decorative wooden stool nearby. A neutral sofa and a hanging punching bag are visible, inviting relaxation.

Apartment in Cole Bay

Les Alysés - 2BR-piscine privative