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Holiday rentals in Oranjestad

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Top-rated holiday rentals in Oranjestad

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

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Guest favourite
The shoreline is captured during sunset, with gentle waves lapping at the sand. The horizon glows with warm hues of orange and yellow, reflecting on the water's surface. Soft clouds dot the sky, complementing the tranquil scene.
Guest house in Frigate Bay
4.88 out of 5 average rating, 115 reviews

Seabreeze Cottage: Pure relaxation near the beach

Enjoy the hospitality of beautiful St. Kitts at Seabreeze Studio Cottage. Seabreeze is a quiet self-contained air-conditioned studio apartment for two with everything you need for a lovely holiday. A 5-minute drive to both the Atlantic Ocean and the Caribbean Sea, restaurants, golf, night-life, and more, the cottage offers indoor and outdoor dining, a kitchen, flat screen TV, wifi, washer, dryer, and lovely Caribbean breezes. We provide towels (bath and beach), pots and pans, and bed linen.

Guest favourite
A view of the charming Saba cottage is framed by tall palm trees, showcasing the traditional gingerbread exterior with a red roof. Lush greenery surrounds the property, with hints of the ocean visible in the distance under a cloudy sky.
Home in Windward Side
4.9 out of 5 average rating, 48 reviews

Beautiful traditional Saba Cottage

This charming 2 bedroom Saba cottage was built in 2007 yet anyone walking by would think the home is one of the original Saba homes. The exterior of the home follows the traditional Saba gingerbread style while the interior is modern and spacious. Located directly in the quaint village of Windward side yet adjacent to the museum and it's beautiful gardens. It's just a short stroll to Windward side's restaurants, bars, stores as well as the start of the hiking trail to Mount Scenery.

Guest favourite
The exterior of a vibrant pink house is framed by green palm trees and lush landscaping. A sloped green roof and white railings on the front porch add charm. A pathway leads to the entrance, showcasing a welcoming approach to the spacious private home.
Villa in Cliftons
4.86 out of 5 average rating, 21 reviews

Private 5 bdrm Villa with Pool

Mandevilla is a private 5 bedroom home with a pool and lots of room for a large family. Walk to nearby beaches, restaurants, and water sports, or take advantage of our discounted car rental rates and explore the entire island. Our local host can help you arrange tours, a private chef, or in-home massage. She can even grocery shop ahead of your arrival so you can just jump in the pool! Once you book your stay we will provide you with a digital guidebook to plan your perfect vacation!

Top guest favourite
A stone cottage features a front porch with white railing, providing an outdoor space for relaxation. Lush greenery surrounds the property, and the clear blue sky enhances the sense of tranquility. The entrance is accentuated by a simple but elegant light fixture.
Holiday home in Windward Side
4.91 out of 5 average rating, 88 reviews

Peter Hytte by Althea

This property in Windwardside features stunning views of the blue Caribbean, the misty top of spectacular Mt. Scenery, and the picturesque village below. On my 30th trip to Saba in 2019 I bought the 1858 vintage Althea Cottage. In 2021 I completed a second stone house for myself at the rear. In 2022 a second stone apartment, Peter Hytte, was built between the two other cottages... smaller, priceworthy and efficient. All net income is donated to my charities. I charge no cleaning fee.

Guest favourite
A weathered wooden dock extends into calm waters, featuring several posts standing tall. In the background, the lush green outline of a mountain rises against a soft sky, creating a serene landscape that invites relaxation.
Home in Southeast Peninsula
4.95 out of 5 average rating, 19 reviews

Yellow House, Turtle Beach

Tranquil spacious Caribbean retreat The simplicity of the design of this characterful family property blends perfectly for relaxed open air Caribbean living. A well equipped kitchen and comfortable lounge area wrap around a spacious part covered terrace which face onto an outdoor seating area and an infinity plunge pool, all of which face across the Narrows to Nevis There are four ensuite spacious bedrooms two of which have their own shaded balcony/veranda for additional privacy.

Superhost
Home in Cades Bay
5 out of 5 average rating, 3 reviews

“FreeBird” - with panoramic volcano & ocean views

Brand New, unique & tranquil, rest with amazing 180’ panoramic east / west views of volcano & ocean. The “freebird” bedroom suite on Nevis island is born out of the chic eccentric lifestyle of its world traveled owners. Decorated with tastes of a Mediterranean chic, ultra lounge & romantic West Indian grooves ❤️ 1 bed / 1 bath with a freestanding soaking tub & candlelight romantic accents Enjoy watching the monkeys, moonrise & sunset from this truly amazing lookout retreat.

Top guest favourite
A tranquil swimming pool is framed by lounge chairs, offering a scenic view of the ocean and distant clouds. Lush greenery borders the area, and a stylish outdoor seating arrangement is positioned to the side, providing a space for relaxation.
Guest suite in Basseterre
4.93 out of 5 average rating, 28 reviews

2BR Apt with Pool & Ocean Views, Near Amenities

Relax in style at our peaceful 2BR poolside apartment, your cozy home away from home. Enjoy stunning views of downtown Basseterre, the harbor, and surrounding mountains. Take a refreshing dip in the pool or explore nearby attractions for a blend of comfort and adventure. Perfect for families, couples, and solo travelers looking for relaxation and adventure. Our retreat offers easy access to local culture and cuisine. Experience relaxation and exploration all in one place!

Top guest favourite
A panoramic view captures the lush hills of Bird Rock with the Caribbean Sea in the background. The foreground features a palm tree and a stone pathway leading to a gazebo area, framed by soft clouds and bright blue skies.
Flat in KN
4.96 out of 5 average rating, 106 reviews

1B Apartment With Amazing Sunsets

Tasia View is nestled in the peaceful hills of Bird Rock. You will enjoy stunning views of the Caribbean Sea and the capital city of Basseterre. Enjoy dinner on the grill as you take in one of our breathtaking sunsets. Try our very own property made St. Kitts Swizzle with local juices and various delicious rums. It truly is a serene, relaxing location where your closest neighbor will be our Vervet monkeys. Please feel at ease and relax while we take care of the rest.

Top guest favourite
An expansive infinity pool extends toward the ocean, framed by lush tropical vegetation. The view captures the serene blue waters and the distant silhouette of Nevis mountain, creating a harmonious blend of nature and tranquility.
Villa in South East Peninsula
5 out of 5 average rating, 68 reviews

Ocean Song Villa & Beach Front Private Lounge

Beautiful Villa with SPECTACULAR ocean views. Carefully designed with the natural elements in mind for very comfortable island living. Situated overlooking Turtle Beach Cove on the tip of the South East Peninsula is the very peaceful and private Ocean Song Villa. Mature tropical gardens with bird life surrounding our Villa. Turtle Beach is a quiet neighbourhood close to some great restaurants and beach bars both "local style" and upscale!

Guest favourite
The modern kitchen features blue-gray cabinetry with a marble countertop, accompanied by a bar area with two wooden stools. Natural light filters in through large glass doors, illuminating the space. A cozy seating area with plush cushions is visible in the background.
Flat in Basseterre
4.92 out of 5 average rating, 13 reviews

The Oasis: Cozy. Calm. Central.

This special place is close to everything, making it easy to plan your visit. Welcome to The Oasis, a charming apartment designed for comfort, relaxation, and convenience. Tucked away in a peaceful setting, this cozy retreat offers the perfect balance of privacy, nature, and access to amazing outdoor amenities. The Oasis is located within proximity of the airport and other local hotspots, including downtown Basseterre.

Top guest favourite
The spacious verandah features wooden flooring and a railing, offering views of palm trees and the distant Island of Nevis. Two wooden lounge chairs are positioned for relaxation, while a colorful striped outdoor bed invites guests to unwind in the fresh air.
Cottage in Cockleshell Bay
4.98 out of 5 average rating, 123 reviews

Coconut Farm Cottage - Cockleshell Beach St Kitts

Our Coconut Farm Cottage is pleasantly placed in the midst of hundreds of coconut trees and a short walk to one of St Kitts most beautiful beaches. We are located right next door to the Park Hyatt Hotel. Great restaurants nearby within walking distance. Relax on the veranda with a cold drink & enjoy the outstanding view of the Island of Nevis over the palms. Truly a spectacular home!

Top guest favourite
The exterior of a bright, two-story loft is showcased, surrounded by lush palm trees and vibrant bougainvillea. The upper deck is visible, reflecting sunlight against a clear blue sky. A shaded parking area is located beneath, adding to the tropical charm of the setting.
Villa in Frigate Bay
5 out of 5 average rating, 18 reviews

Beach Condo | Walk to Bars, Dining & Taxi

In the heart of Frigate Bay, our two-bedroom offers 2 queen-size beds, fast Wi-Fi, a smart TV, a fully family-ready kitchen, and three stunning outdoor spaces—one on each level—where you can start your mornings with coffee under swaying palms and relax in bright, breezy interiors. Experience the magic of a true island paradise and make this your home away from home!

Popular amenities for Oranjestad holiday rentals