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Holiday 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.

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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, 63 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.

Guest favourite
Condo in Sint Maarten
5 out of 5 average rating, 6 reviews

Apt4 (1 bedroom with terraces & amazing sea view)

Warm and Intimate Triplex with 1 Master bedroom, with sea and pool view. Located in Black Palm, an elegant residence of 6 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 2 guests: couples or friends 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.

Top Guest favourite
Condo in Maho
4.91 out of 5 average rating, 231 reviews

Maho Love Shack: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.

Top Guest favourite
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
4.96 out of 5 average rating, 136 reviews

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

The "SeaBird studio" is ideally located with a beautiful view of the Caribbean Sea and an idyllic beach just for you! It offers plenty of comfort and storage with refined and original decoration. The residence is perfectly secure with a large swimming pool and tropical garden. Everything is within walking distance: grocery store, local market, shops, traditional or gourmet restaurants, ferry station to other islands, etc... High-speed Wi-Fi and TV Europe and America.

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, 178 reviews

Sea Loft, Breathtaking View – Private Pool

* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with lounge chairs, garden furniture, outdoor table and BBQ * Office area * 100 Mbps Wi-Fi * 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, boutiques and other shops * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

Guest favourite
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
4.92 out of 5 average rating, 13 reviews

Les Alysés - 2BR-private pool

Book your stay in the sun in this beautiful apartment located on the ground floor of a hacienda-style villa. The turquoise water pool and the garden where you can enjoy meals in the shade of the Cycas will be fully reserved for you. The apartment, furnished in a Caribbean style, offers two bedrooms with TV and air conditioning, a bathroom with a large shower, a fully equipped kitchen and a spacious living room with a punching bag and foosball.

Guest favourite
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.
Apartment in Point Pirouette
4.91 out of 5 average rating, 130 reviews

Secret View amazing apartment- Private pool

Welcome to Secret View! An elegant and intimate retreat with a private pool and a spacious terrace set directly on the lagoon. Designed for couples seeking calm, romance and discretion, just minutes from vibrant Maho with its restaurants, bars and casinos, and Mullet Bay Beach, one of the island’s finest beaches with stunning turquoise waters. Free private parking. This hidden gem is the perfect setting for unforgettable moments together.

Guest favourite
A bright terrace features a small dining table and chairs, overlooking the beach and crystal blue waters. Light-colored tiles create an open and inviting feel, while a cozy seating area offers unobstructed views of the sea. The sky is clear, enhancing the tranquil ambiance.
Apartment in Baie Nettle
5 out of 5 average rating, 5 reviews

Stunning Sea View – 1min Walk to the Beach & pool

Wake up to the endless blue of the Caribbean from your private terrace with breathtaking sea views. This beachfront apartment in Baie Nettle combines comfort, elegance, and serenity. Direct beach access, 4 pools, 2 tennis courts, Wi-Fi, A/C, and fully equipped kitchen. Ideally located between the French and Dutch sides, near top beaches and restaurants. A perfect escape for couples, remote workers, or anyone seeking peace.

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, 166 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 !

Guest favourite
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 Cole Bay
4.92 out of 5 average rating, 52 reviews

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.

Top 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
4.94 out of 5 average rating, 120 reviews

Independent apartment at the bottom of the villa – Indigo Bay

The Villa Stella apartment welcomes you in a unique setting with spectacular views of the Caribbean Sea. Located in a 24-hour secure residence, tranquility awaits. You will be just an 8-minute walk to Indigo Bay Beach and close to shops and restaurants in the Dutch side. Composed of 2 bedrooms and 2 bathrooms, you can relax in the pool/jacuzzi overlooking the bay.

Top Guest favourite
A private outdoor area features a swimming pool surrounded by lounge chairs, with views of the water and distant hills. Palm trees provide shade, while a wooden structure offers a dining space. Natural stone tiles create a welcoming atmosphere, ideal for relaxation.
Villa in Cul-de-Sac
4.99 out of 5 average rating, 149 reviews

VILLA JADE 2: WATERFRONT SUITE/POOL

VILLA JADE is a complex of 3 villas located in the bay of CUL DE SAC and its islets... VILLA JADE 2 is a spacious/sea view suite for 2 people on the water, with a private pool. The 3 villas are adjoining but very quiet and private. Your unique view is the sea... Direct access to the sea via a pontoon, and kayaks at your disposal.

Popular amenities for Cole Bay rentals with a pool

When is the best time to visit Cole Bay?

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Avg. price$479 NZD$479 NZD$463 NZD$479 NZD$389 NZD$423 NZD$413 NZD$360 NZD$329 NZD$379 NZD$415 NZD$481 NZD
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Quick stats about holiday rentals with a pool in Cole Bay

  • Total holiday rentals

    Explore 380 holiday rentals in Cole Bay

  • Nightly prices starting at

    Cole Bay holiday rentals start at $50 NZD per night before taxes and fees

  • Verified guest reviews

    Over 4,180 verified reviews to help you choose

  • Family-friendly holiday rentals

    150 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wi-Fi availability

    370 of Cole Bay holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Cole Bay rentals

  • 4.8 Average rating

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