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Holiday rentals in Cay Bay Hill

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Top-rated holiday rentals in Cay Bay Hill

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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.
Flat in Simpson Bay
5 out of 5 average rating, 62 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
A serene beach view is captured, showcasing clear turquoise waters meeting powdery white sands. A picnic table sits on the beach, bordered by vibrant green plants and palm trees. Soft clouds drift above under a bright blue sky, completing the tranquil seaside scene.
Flat
4.96 out of 5 average rating, 211 reviews

Lilly's Beach

This is a very SPECIAL SMAll RESIDENCE known as Ocean Edge . Beach Front located directly on beautiful Simpson Bay Beach! Enjoys one of the best locations on the island . Panoramic sea views with your toes in the sand and balmy Caribbean breezes. A clear turquoise sea dazzles in tropical sun, powdery white sands stretching along one of St. Maarten's longest beaches. Apartment with modern amenities and comforts. A perfect vacation spot ! Back up system installed to insure electricity.

Guest favourite
Apartment 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
Flat in Simpson Bay
5 out of 5 average rating, 227 reviews

The Beach House Apartment

A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more

Guest favourite
A spacious verandah features a comfortable seating area with a light-colored couch and a dark wicker coffee table. Lush greenery is displayed in a yellow planter, with panoramic views of the hills and bright blue sky in the background.
Home in Indigo Bay
4.77 out of 5 average rating, 191 reviews

La Pearle - Luxurious 1 Bedroom Condo By the Beach

Nestled on the hills of Indigo Bay, La Pearle is located midway between Philipsburg and the Simpson Bay touristic hang out. La Pearle exudes relaxation the minute you walk through the door! Awake to watching the Allure of the Seas make its way into the harbor. La Pearle, elegant, sophisticated and distinguished! The 1- bedroom spacious condo sleeps two! Experience luxury with a huge verandah overlooking the Indigo beach, Caribbean living, yours to enjoy!

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
4.99 out of 5 average rating, 175 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

Top guest favourite
The infinity pool is visibly stretching towards the horizon, blending with the calm turquoise waters of the Caribbean Sea. Palm trees frame the scene, while a cruise ship can be seen cruising in the distance under a clear blue sky.
Flat in Philipsburg
4.97 out of 5 average rating, 32 reviews

Studio Ocean Front, Infinity Pool

Clearwater is a cliffside waterfront property with one of the most spectacular views on the island! Overlooking Great Bay, Philipsburg, Divi Little Bay, the turquoise Caribbean Sea and the magnificent cruise ships, this one of its kind location will be sure to put you at awe. It is perfectly situated for easy access to all SXM has to offer; restaurants, beaches, grocery stores, downtown shopping, bars and entertainment.

Top guest favourite
The living area features modern furnishings, including a light sofa, a coffee table, and two armchairs. A dining area with a wooden table is visible, along with large sliding doors that reveal an ocean view and a spacious balcony. Natural light floods the space.
Apartment in Sint Maarten
4.97 out of 5 average rating, 32 reviews

Casa Nova, Indigo Bay SXM

CasaNova is an newly built condo in the Indigo Bay gated community. If you like a good view. This place is for you. It’s a 5 minute walk to the beautiful Indigo Bay Beach. The snorkelling will not disappoint. Explore the sunken ship and meet the resident octopus. Have breakfast on our 300sq-ft balcony while overlooking the ocean. Its modern construction methods deliver a comfortable, safe and cool vacation home.

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.
Flat in Little Bay
4.99 out of 5 average rating, 164 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
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.
Flat
4.97 out of 5 average rating, 36 reviews

CondoSTmaarten panoramic (Adults Only)

Condo St. Maarten is located in the quiet and secure subdivision of Indigo Bay. 8 miles or 5 km from Juliana Airport. Ideally located between the Dutch capital Phillipsburg with its beautiful bay lined with a long white sandy beach, duty free shops, cruise boats and Simpson Bay renowned for nightlife, casinos, restaurants and night clubs. Supermarkets are a 5-minute drive away.

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.
Flat in Indigo bay
4.94 out of 5 average rating, 117 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
An infinity pool extends toward the horizon, offering uninterrupted views of the Caribbean sea. The clear blue water reflects the sky, creating a serene atmosphere. Gentle slopes of greenery frame the scene, with a distant island visible on the water's surface.
Villa in Philipsburg
4.99 out of 5 average rating, 306 reviews

Villa Dream View Belair Sint Maarten SXM

Embrace the tranquility in a friendly tropical caribbean modern designed private villa with spacious rooms that are sure to keep you comfortable and feeling at home. Enjoy the sunny day with infinity pool overlooking caribbean sea or enjoy the sea view while watching the sailing huge cruise ships.

Popular amenities for Cay Bay Hill holiday rentals