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Vacation rentals in Cay Bay Hill

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Top-rated vacation rentals in Cay Bay Hill

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Top guest favorite
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 favorite
Large glass sliding doors open to a sunny outdoor deck with views of the turquoise ocean. Comfortable lounge chairs and a dining table are visible among tropical palm trees. The living area features a soft gray couch and a wall-mounted TV, creating an inviting indoor space.
Apartment in Simpson Bay
5 out of 5 average rating, 220 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

Superhost
A scenic view showcases lush greenery, with a body of water reflecting the sky and distant hills. The ocean is visible on the horizon, framed by clouds and bright blue sky, creating a serene natural landscape.
Guesthouse in Little Bay
4.91 out of 5 average rating, 46 reviews

Studio near the beach

Small lovely studio in a quiet, peaceful and secure neighborhood. The studio is air-conditioned and perfect for the budget traveler and with about 25m2 it is spacious enough for 2 guests. The studio is equipped with a small kitchenette and a full bathroom. Located within a 10-minute walk to Belair beach and a 5-minute walk to the hospital. Philipsburg is a 5 minute drive away. Note: The studio has a shared entrance and is located next to the main house where the host resides.

Top guest favorite
An outdoor terrace features comfortable white lounge furniture arranged around a central table, overlooking serene ocean views. A private pool is visible beyond the terrace, complementing the clear blue sky and tranquil waters.
Villa in Sint Maarten
5 out of 5 average rating, 15 reviews

Indigo Oceanfront Condo Poolside - Unit 1

Welcome to Indigo Bay Oceanview Villa, in Indigo Bay, Sint Maarten. This spacious condo offers stunning ocean views, modern amenities, and easy access to pristine beaches. With 3 elegant bedrooms, each featuring en-suite bathrooms, an open-concept living area with plush seating, and a gourmet kitchen equipped with state-of-the-art appliances, you’ll find everything you need for a perfect stay. Step outside to your private pool, sun deck, and shaded patio for alfresco dining.

Top guest favorite
An infinity pool reflects the bright blue sky and shimmering sea, creating a tranquil contrast. The edges of the pool are lined with clear glass panels, providing unobstructed views of the horizon. The sunlight sparkles on the water's surface, emphasizing the serene setting.
Home in Indigo Bay
5 out of 5 average rating, 20 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.

Superhost
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, 180 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 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, 170 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 deckchairs, garden furniture, outdoor table and BBQ * Office space * 100 Mbps WiFi * 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, shops and other stores * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

Guest favorite
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.
Apartment in Sint Maarten
4.97 out of 5 average rating, 31 reviews

CondoSTmaarten panoramic (Adults Only)

Condo st Maarten se trouve dans le lotissement calme et sécurisé de Indigo Bay. 8 miles ou 5km de l'aéroport de juliana. Idéalement situé entre la capitale hollandaise Phillipsburg avec sa magnifique baie bordée d’une longue plage de sable blanc, ses boutiques duty free, ses bateaux de croisières et Simpson Bay réputée pour la vie nocturne, ses casinos, restaurants et night clubs. Des supermarchés se trouvent à 5 minutes en voiture.

Guest favorite
A dining area is presented with a modern table surrounded by four black chairs. Above, a colorful artwork adorns the wall, complementing the vibrant decor. Two candles on the table add an elegant touch, while soft lighting from above enhances the welcoming ambiance.
Condo in Cole Bay
4.83 out of 5 average rating, 127 reviews

Convenient, Near Airport, Free Parking + Security.

Cozy 1 bedroom apartment that is centrally located in a gated community in Cole Bay. This area is situated on the Dutch side of the island, but it is near the French side of the island. The apartment is 10 minute drive from the Princess Juliana International Airport. In the area, there is a small supermarket which is 1 minute walking distance and Lagoonies Bistro & Bar which is 2 minute walking distance from the apartment.

Top 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
5 out of 5 average rating, 30 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.

Top 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, 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 !

Guest favorite
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, 108 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.

Popular amenities for Cay Bay Hill vacation rentals