Some info is shown in its original language. Translate

Vacation rentals with a pool in Cole Bay

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Cole Bay

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

%{current} / %{total}1 / 1
Guest favourite
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
4.97 out of 5 average rating, 92 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

Top guest favourite
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
5 out of 5 average rating, 55 reviews

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.

Top guest favourite
An open-concept living space features large sliding glass doors that reveal views of the tranquil bay. A dining area with a wooden table and upholstered chairs sits centrally, complemented by a cozy sofa adorned with colorful throw pillows. A vibrant platter of fresh fruit and charcuterie adds a decorative touch.
Villa in Indigo Bay
5 out of 5 average rating, 18 reviews

Villa Solandra – 3BR Oceanfront Sunset w/ Pool

Welcome to Villa Solandra, a western facing ocean front luxury 3BR/3BA home with a private pool in Indigo Bay. Enjoy romantic & epic sunsets, this cliffside escape blends indoor-outdoor living with sweeping Sea & Bay views, two large oceanfront balconies, and designer interiors. Enjoy a chef inspired kitchen, luxury king suites w/ ensuite baths, private garden just minutes from beaches, dining, Simpson Bay and Maho’s iconic plane spotting. Perfect for families, friends, or romantic getaways.

Top guest favourite
An outdoor terrace features a private swimming pool surrounded by lounge chairs. Sunlight filters through a slatted pergola, creating patterns on the patio. Lush greenery and colorful flowers are visible, with views of yachts and the lagoon beyond.
Condo in Cole Bay
5 out of 5 average rating, 46 reviews

PARADISE ONE TO LAS BRISAS

A proximité de l'aéroport international de JULIANA [10 min], nous vous proposons un appartement de luxe, dans une très belle résidence sécurisée, en bord de lagon, avec une piscine et un jardin PRIVE, qu'une magnifique vue sur les yatchs durant la haute saison. Pour les sorties nocturnes, vous serez idéalement situés, non loin de Simpson Bay, avec de nombreux restaurants, casinos, boites de nuit ect... Possibilité de faire de footing, qui est une attraction incontournable de l'île.

Top guest favourite
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
4.99 out of 5 average rating, 171 reviews

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

Superhost
Home in Calabash Rd, Cole Bay
4.9 out of 5 average rating, 154 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 !

Guest favourite
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
4.95 out of 5 average rating, 110 reviews

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 .

Top guest favourite
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.
Villa in Indigo bay, Sint Maarten
5 out of 5 average rating, 31 reviews

Ocean Dream Villa

Indulge in luxury at a two-bedroom villa in Indigo Bay, Sint Maarten. Enjoy modern elegance, a private pool, and ocean views. Relax indoors or outdoors, savor gourmet meals, and unwind under starlit skies. Luxurious bedrooms offer ocean vistas. Whether for romance or family, this villa promises a memorable Caribbean escape at Ocean Dream, where luxury meets natural beauty. Book now for an extraordinary island retreat.

Superhost
A clear glass of champagne rests atop a woven placemat, beside a vibrant vase filled with pink flowers. In the background, a stunning view of turquoise waters and lush green hills can be seen under a partly cloudy sky.
Cottage in Sint Maarten
4.92 out of 5 average rating, 108 reviews

«La Vue SXM» Luxe "Villa La Vue" + Beach/Bar/Food

Located in private gated community Indigo Bay, minutes from beach. Villa has private infinity pool and is neighbored by large communal pool. Modern art déco 2 floor villa has 3 bedrooms, 3 full bathrooms, equipped kitchen, balcony, and terrace with ocean views. **Construction of new hotel began in Indigo Bay as of March 2025 which impacts the entire bay** Free : - Champagne on arrival - 1 Mid Housekeeping Services

Top guest favourite
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
4.99 out of 5 average rating, 158 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 !

Superhost
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
4.83 out of 5 average rating, 190 reviews

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!

Superhost
Apartment in Cole Bay
5 out of 5 average rating, 3 reviews

C342 - Glorious Lagoon View Apartment with Balcony

Welcome to Apartment C-342 at The Hills Residence Vacation Rentals! Located on the fourth floor of Building 3, this stunning apartment offers an elevated perspective with spectacular views of Simpson Bay. Its prime location makes it the perfect retreat, offering both a peaceful getaway and easy access to local attractions.

Popular amenities for Cole Bay rentals with a pool

When is the best time to visit Cole Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$406 CAD$406 CAD$392 CAD$406 CAD$329 CAD$358 CAD$350 CAD$305 CAD$278 CAD$266 CAD$315 CAD$359 CAD
Avg. temp26 °C26 °C26 °C27 °C28 °C29 °C29 °C29 °C29 °C29 °C28 °C27 °C

Quick stats about vacation rentals with a pool in Cole Bay

  • Total vacation rentals

    Explore 350 vacation rentals in Cole Bay

  • Nightly prices starting at

    Cole Bay vacation rentals start at $42 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,990 verified reviews to help you choose

  • Family-friendly vacation rentals

    150 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wifi availability

    340 of Cole Bay vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Cole Bay rentals

  • 4.8 Average rating

    Cole Bay stays are highly rated by guests—averaging 4.8 out of 5!