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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Top guest favourite
The cottage features a red metal roof and white exterior, set in a lush, tropical landscape. A spacious deck with colorful chairs and an umbrella offers a spot for relaxation. Surrounding greenery and nearby buildings create a charming, community atmosphere.
Cottage in Windward Side
4.98 out of 5 average rating, 96 reviews

Althea Cottage

This cottage was built in a bygone era (1858) in Windwardside and features stunning views of the blue Caribbean, the misty top of spectacular Mt. Scenery, and the picturesque village below. Within 1-3 min you can walk to 2 grocery stores, 7 restaurants, 2 coffee shops, a bakery, 3 bars, the PO, 2 tourist shops, 2 churches, and a lovely park with museum. All net income is placed into a trust fund for my charities. I've become more of a minimalist in my retirement. I charge no cleaning fee.

Superhost
A close-up view of the infinity pool reveals clear blue water reflecting sunlight. The pool's edge blends seamlessly into the surrounding lush greenery, creating a tranquil atmosphere. The horizon meets the sky, providing a serene backdrop for relaxation.
Villa in Frigate Bay
4.91 out of 5 average rating, 78 reviews

Oceanfront Villa w/ Infinity Pool & Near Beaches

Escape to Your Private Oceanfront Paradise 🌴 Experience island living at its finest in our luxury beachfront villa — ideal for families, groups, and anyone seeking sun, sea, and serenity. 🌊 Breathtaking ocean views from the large deck and infinity pool Steps from beaches, golf, shopping, and nightlife tennis court & outdoor living space Fully equipped kitchen, BBQ, and shaded relaxation areas Free parking + reliable Wi-Fi and workspace Perfect for families, couples, and beach lovers

Guest favourite
Flat in Palmetto Point
5 out of 5 average rating, 14 reviews

Palmetto Bay Paradise

Forget your worries in this spacious and serene space. Sit on your Veranda with a Cocktail and watch the Lit Up Cruise ships pass you by. Enjoy the panoramic view of the mountains and sounds of the Ocean. Palmetto Bay is a 5 minute walk, where you can kick back and take a dip in the Ocean. This Apartment has a fully functional kitchen with cooking equipment incl. Stove, Ninja Air Fryer, Microwave, Fridge freezer, Coffee maker, Kettle, Toaster, Blender, Dishes, Cutlery and much more....

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, 50 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
A living area is depicted with two light grey sofas positioned around a coffee table. A large flat-screen television is mounted on a wooden media console. A fan hangs from the ceiling, and a staircase is visible in the background, along with a textured wall.
Flat in Frigate Bay
4.89 out of 5 average rating, 64 reviews

Shalimar Apartment 4

Shalimar is situated just a few minutes walk from a world class golf course, a short drive from the beach and the local entertainment area known as "The Strip" along with a variety of authentic restaurants offering cuisine from around the globe. Our two bedroom apartments are tastefully furnished and enjoy spectacular views across the golf course toward the Atlantic Ocean. Each apartment includes fully fitted modern kitchen, dining area and living room and an open patio to enjoy.

Superhost
A vibrant yellow two-story structure features a spacious covered patio with decorative columns. The upper balcony, bordered by sleek railings, offers ample outdoor space. Two sets of doors are visible on the ground level, while several windows provide natural light.
Townhouse in Newton Ground
5 out of 5 average rating, 6 reviews

Goose Hollow #2

Take it easy at this unique and tranquil getaway. Sea view on one side, mountain view on the other. Get away from the hustle and bustle of the city and come get away to a peaceful paradise. Wake up with the roosters and catch sight of some cows, goats and sheep just outside your fenced in home. 14 miles from the city. About a 30 minute drive from the airport. **Please note that the home features air conditioning in the bedrooms only, while the living areas remain uncooled.

Guest favourite
The cottage is framed by lush greenery, offering views of calm blue waters and distant hills. A white adirondack chair sits on a stone patio, inviting relaxation as waves gently lap at the shore. The sky is clear and bright, enhancing the serene landscape.
Cottage in South East Peninsula
4.97 out of 5 average rating, 93 reviews

Two for One Charming Cottage & Turtle Beach Lounge

Situated overlooking quiet Turtle Beach on the South East Peninsula is a very peaceful & private cottage on the hillside with stunning ocean views! Enjoy your morning coffee while watching the pelicans dive for their breakfast. Keep an eye out for sea turtles on the amazing reef below the cottage. Hummingbirds buzz around you in the gardens. Have a sunset drink and be amazed at the outstanding view of Nevis! Guests have the use of a beach front private day lounge.

Guest favourite
An open balcony is shown, framed by wooden doors that create an inviting entry. The view encompasses blue ocean waters and lush greenery, with a palm tree visible against the clear sky. The space offers a serene atmosphere, perfect for relaxing.
Flat in Halfmoon Heights
5 out of 5 average rating, 27 reviews

Sunrise Studio

Welcome to your dream escape. Nestled on a serene hillside, this stunning home offers breathtaking panoramic views of the Atlantic Ocean and lush fairways of the golf course. This 1 bedroom, 1 bath Apt, open-concept, fully equipped kitchen and spacious terrace/workspace is for you . Wake up to the morning sunrise, relax in the breezy evening moonlight. Vehicle required to access restaurants , beach and golf course. Experience the ultimate getaway!

Top guest favourite
Flat in Basseterre
5 out of 5 average rating, 23 reviews

St Kitts Castle Suites, Unit 2, Frigate Bay

St. Kitts Castle Condominiums, set in a quiet luxury residence near Frigate Bay and South East Peninsula, offers a spacious 1-bedroom apartment with 1 bathroom (shower & free toiletries). Enjoy a fully equipped kitchen with range stove, refrigerator, dishwasher, kitchenware, and coffee machine. The air-conditioned unit features a living area with flat-screen TV, dining space, private entrance, washing machine and dryer, and 2 beds (queen + sofa bed).

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
4.94 out of 5 average rating, 18 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, 125 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!

Guest favourite
Flat in Princess Garden
4.92 out of 5 average rating, 12 reviews

Spacious Stay in Statia

This spacious apartment is perfect for group trips. It is on the second floor and has amazing views of the Caribbean sea, the Quill and the beautiful island. There is a spacious kitchen, a patio and a large back porch available for outdoor dining. Local Souvenirs available for purchase here. Car rentals are also available via us with Brown’s Car Rental. Taxi service also available.

Popular amenities for Oranjestad holiday rentals