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Vacation rentals in Cay Bay Hill

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Top-rated vacation rentals in Cay Bay Hill

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
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
4.95 out of 5 average rating, 76 reviews

Villa Ocean - Indulge Yourself in Paradise

A three-bedroom, two-bathroom beauty overlooking beach/vast views of the ocean in Indigo Bay. Sunset viewing on the deck, private pool or down to the beach 10 min by walking. 10 min to airport, night life, other popular beaches. Close to town. groceries, restaurants. All the bedrooms have a view of beach and the ocean. There is free wireless internet, TV, air conditioning, a dishwasher, refrigerator, microwave, wine refrigerator, coffee maker, washer dryer, outdoor gas grill and private parking.

Top guest favorite
Condo in Sint Maarten
5 out of 5 average rating, 17 reviews

Delight (Apt4) - Amazing Sea View # 1 bedroom

Warm and Intimate Triplex with 1 Master bedroom, 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 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 favorite
Villa in Philipsburg
5 out of 5 average rating, 12 reviews

Ocean View Villa Little Bay

🌴 Villa Little Bay – Oceanview Bliss With 360° Views Enjoy the peaceful sound of the waves and a serene, private atmosphere that’s still close to everything. We’re located within walking distance to Philipsburg, the vibrant heart of SXM—Front Street, top shopping, restaurants, and the island’s best casinos. The beach is just 5 minutes away, Step outside to your private patio for sunbathing, and shimmering ocean‑view pool. Villa offers the perfect blend of tranquility and convenience.

Guest favorite
Apartment in Sint Maarten
4.98 out of 5 average rating, 41 reviews

CondoSTmaarten panoramic (Adults Only)

Discover an exceptional panoramic beachfront apartment overlooking Indigo Bay Beach, located in a private, peaceful residence. You will love the panoramic bedroom with its breathtaking ocean view right from your bed. From your private terrace, enjoy stunning views of the ocean, cruise ships heading to the port, and magnificent Caribbean sunsets. Ideally located between Philipsburg, and the vibrant nightlife of Simpson Bay, the property offers a prime location just 5 miles from SXM airport

Top guest favorite
Apartment in Simpson Bay
5 out of 5 average rating, 242 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

Top guest favorite
The villa features a modern design with two levels, surrounded by lush greenery. An infinity pool is situated in front, with reclining chairs positioned nearby. The outdoor dining area is visible, and the expansive glass windows reflect the vibrant surroundings, inviting natural light into the space.
Villa in Indigo Bay
5 out of 5 average rating, 27 reviews

Life's Good

Located in the only planned community in Sint Maarten in the beautiful and gated “Indigo Bay”. The whole villa to yourself and just 10 minutes from the airport. Villa "Life’s Good" with infinity pool is located on the mountainside with a 180 degree view of the sea and view of the Islands, Saba, St Kitts & Nevis and Sint Eustatius.. A spectacle of breathtaking sunrises and sunsets. Just a 3 minute drive from the villa: are beaches, restaurants and all amenities.

Guest favorite
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
4.78 out of 5 average rating, 209 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!

Guest favorite
An aerial view of the villa showcases its modern architecture with a terracotta-tiled roof and expansive outdoor spaces. A large infinity pool reflects the surroundings, while shaded areas with loungers and a fire pit area provide spaces for relaxation and gathering.
Villa in Upper Prince's Quarter
4.95 out of 5 average rating, 119 reviews

The Blue Door Villa - 4 bed ocean view home

At the Blue Door Villa, we offer our guests all the creature comforts of being in a well-equipped vacation home. We are located on the Dutch side, minutes from the French border in a quiet gated community. The Blue Door Villa is a perfect place to relax while you listen to ocean waves and swim in the infinity pool. There are multiple outdoor spaces offering privacy or space to gather. We are now offering our guests an exclusive, free concierge service.

Top guest favorite
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, 190 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 favorite
An octagonal jacuzzi is positioned on a wooden deck, surrounded by lush greenery. Two lounge chairs are placed nearby, providing a comfortable seating area. The view overlooks a scenic landscape with hints of distant hills under a bright sky, creating a serene outdoor ambiance.
Apartment in St Martin
4.92 out of 5 average rating, 100 reviews

The Perch - A unique jungle experience.

Welcome to The Perch, a different side of St. Martin! Discover breathtaking views and be surrounded by nature. A unique experience with iguanas in the trees and the sound of monkeys echoing through the valley. This exclusive property is the nature lover's paradise, perfect for those seeking to get away from it all while being centrally located only 10 mins from the beach. *Spa services *No children *No parties Social Media: #theparadisepeak

Guest favorite
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
4.95 out of 5 average rating, 59 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.

Guest favorite
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, 175 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 !

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