Vacation rentals in Oranjestad

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Top-rated vacation rentals in Oranjestad

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Top guest favorite
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, 86 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.

Top guest favorite
A spacious living area features large sliding glass doors that open to stunning ocean views. Comfortable seating is arranged on a light-colored sofa, complemented by patterned cushions. A decorative area rug lies on the tile floor, enhancing the inviting atmosphere of the room.
Home in Frigate Bay
4.98 out of 5 average rating, 49 reviews

Sea Breeze

Unwind in this lovely property. Enjoy amazing views and beautiful sunsets over the Caribbean Sea and to the island of Nevis. Sea Breeze has space and privacy for you to relax, recharge and soak up the sun. Located in beautiful Frigate Bay, perfect to access the whole island. Frigate Bay 'Strip' is close by, with restaurants and lovely beach bars serving Caribbean and international cuisine Embrace the 'island time' vibe! Rush slowly! on the beach, with the warm sand under your feet!

Guest favorite
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, 49 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.

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
4.87 out of 5 average rating, 30 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 favorite
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
4.95 out of 5 average rating, 107 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.

Guest favorite
Villa in Half moon Bay
5 out of 5 average rating, 8 reviews

Half moon family and friends getaway

Relax with family and/or friends at this peaceful place to stay. The house is located in a quiet neighbourhood, minutes from shops, restaurants and beautiful beaches. It is a perfect spot to relax and soak up the sun or to come home to after exploring all the island has to offer. The house has a large fully equipped kitchen with a view of the pool and ocean. The pool has a shallow end with built in seating for relaxing and a deep end to jump in and play.

Top guest favorite
Apartment in Basseterre
5 out of 5 average rating, 20 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 favorite
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
4.94 out of 5 average rating, 16 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 favorite
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, 124 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!

Superhost
Apartment in Princess Garden
4.9 out of 5 average rating, 10 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.

Top guest favorite
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, 21 reviews

Seaside Charm: Steps to Beach, bars & island Fun

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!

Guest favorite
A panoramic view of Basseterre and the Caribbean Sea is featured, framed by lush greenery. The majestic Nevis Peak rises in the background, while fluffy clouds hover above. The calm, reflective waters exhibit variations of blue, creating a serene backdrop to the coastal town.
Apartment in Basseterre
4.96 out of 5 average rating, 107 reviews

Tranquil Basseterre AirBnB - 10% Off April 2026

This cozy apartment is nestled 10 minutes drive from the airport and the center of Basseterre and 10 minutes walk to public transportation, supermarkets and night life. You’ll love most of all its location for its spectacular view. Wake up to images of Basseterre and Nevis every day. Take walks in the community and enjoy the panoramic view of your surroundings.

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