Holiday houses in Oranjestad

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Top-rated holiday rentals in Oranjestad

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Superhost
Tiny home in Basseterre
5 out of 5 average rating, 3 reviews

Coffee and Cream Cubby

Welcome to our cozy tiny home designed for comfort & function. The open-plan space includes a well-equipped kitchen, a clever dining area and a cozy lounge. The kitchen features a full-size washer, a space-saving induction cooktop, and a flip-up mini oven. The dining area has a folding table with wall-hung chairs. Sleep soundly in the snug loft bedroom with access via the staircase that doubles as smart storage. It has a separate bathroom with a shower adding convenience Perfect for two!

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
4.92 out of 5 average rating, 76 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

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
4.97 out of 5 average rating, 79 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, 6 restaurants, 3 bars, the PO, a dive shop, 2 tourist shops, 2 churches, and a lovely park with museum. All net income is donated to my charities. I've become more of a minimalist in my retirement, enjoying people over things. I charge no cleaning fee.

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
A tranquil swimming pool is framed by vibrant tropical plants and palm trees. Lounge chairs are arranged around the pool area, while a three-story condominium building is visible in the background, featuring balconies and well-maintained landscaping.
Apartment in Basseterre
4.79 out of 5 average rating, 29 reviews

Silver Reef 3 Bedroom Flat

We offer to stay at the most picturesque place of the island, apartments with a Caribbean flavor. Cozy three-bedroom apartments are located in the heart of the Frigate Bay, overlooking the garden and the Caribbean Sea in the Silver Reef condominium. The Royal St Kitts Golf Course, the Frigate Bay beach with a magnificent coastline of the Caribbean Sea within walking distance nearby, lively cafes and restaurants on the Atlantic coast - all these create wonderful Caribbean atmosphere.

Superhost
A tranquil outdoor pool area features several lounge chairs and vibrant green umbrellas. Lush palm trees and various plants create a tropical atmosphere around the pool's edge, with blue mosaic tiles lining the water.
Apartment in Basseterre
4.86 out of 5 average rating, 29 reviews

Shalimar Vacation Apartment 1

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.

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.
Apartment in KN
4.96 out of 5 average rating, 104 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 aerial view captures the expansive pool area surrounded by lounge chairs and stylish landscaping. A grill station is positioned nearby, with shaded seating beneath elegant wooden trellises. The tranquil water of the pool reflects the bright sky, inviting relaxation and enjoyment.
Guest suite in Basseterre
4.96 out of 5 average rating, 25 reviews

Chic & Cozy 2BR Retreat + Pool

Relax in style at our chic 2BR apartment, your cozy home away from home. Enjoy breathtaking views of downtown Basseterre, the harbor, and the mountains. Dive into the refreshing pool or explore nearby attractions for a comfortable, scenic getaway. Perfect for global travelers seeking a peaceful retreat, our welcoming environment ensures a memorable stay with easy access to local culture and cuisine. Experience the ultimate relaxation and adventure all in one place!

Top 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.
Apartment in Halfmoon Heights
5 out of 5 average rating, 23 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!

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.
Apartment in Basseterre
4.92 out of 5 average rating, 12 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, 122 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, 17 reviews

Coastal Charm: Steps to Beach, Eats & 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