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Vacation rentals in North Side

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Top-rated vacation rentals in North Side

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Top guest favourite
A modern one-bedroom house is framed by a sleek security gate, ensuring privacy. A white car is parked in a gravel driveway, with landscaped greenery visible in the background. The clean lines of the building are complemented by large windows and a bright exterior.
Home in North Side
5 out of 5 average rating, 32 reviews

Beautiful newly built one bedroom entire house

A beautiful, newly constructed one bedroom house with modern styling. Highlights include fully air-conditioned space, king sized bed,dual 55 inch TVs with full IPTV channels and streaming services, security gate, security cameras on property, fully equipped kitchen, laundry room with washer and dryer and much, much more. The property is located centrally but offers utmost privacy. No expense was spared to provide a unique, high end experience for your pleasure. We look forward to welcoming you!

Superhost
Apartment in Bad Cox Pond
5 out of 5 average rating, 4 reviews

Infinity sunset.

This modern accommodation is ideal for couples' trips, offering ample space and comfortable amenities. Located in a prime area, a 5-minute drive to Shoal Bay Beach, guests can unwind and take in a breathtaking ocean view from the top floor, which features a serene pond surrounded by vibrant local flora. The view stretches as far as the eye can see, providing a perfect backdrop for relaxation and memorable gatherings. This place is truly a hidden gem for those seeking both adventure and comfort.

Top guest favourite
A bright terrace dining area features a large white table surrounded by six chairs. A Weber grill is positioned nearby, and stunning views of the turquoise sea and anchored boats are visible through expansive glass walls, allowing natural light to fill the space.
Apartment in Sandy Ground
5 out of 5 average rating, 28 reviews

Enclave 3 Luxury Beachfront Penthouse

Luxury brand new beachfront penthouse directly on beautiful Sandy Ground Beach. This spacious third floor unit is 1,640 square feet. The unit has two terraces, a walk-in shower with handheld & rain shower, a gourmet kitchen, and more. Location is ideal as you can walk to ten plus restaurants. Being on the Caribbean side of the island, the beach is typically always calm & crystal clear. Amenities include Viking appliances, SONOS in ceiling speakers, Tempurpedic mattresses, and much more

Top guest favourite
Home in Shoal Bay Village
5 out of 5 average rating, 65 reviews

Seaside House in Shoal Bay

Shoal Bay Cottage is located next to one of the best beaches in Anguilla if not the world, Shoal Bay East. This 2 bedroom, 2 bathroom property comes with all the modern luxuries. Suitable for individuals, couples, families or friends. Enjoy its almost 0.5 acres of fenced gardens or within 3 mins walk you are on the beach. There, you will enjoy, miles of pristine white sand, cool turquoise water, and gentle sea breeze. As well as, many of the popular hotels, and restaurants.

Top guest favourite
The exterior of the studio apartment showcases a charming two-story building adorned with vibrant orange and white hues. Lush garden vegetation, including pink bougainvillea, frames the entrance, and a welcoming staircase leads to the private entrance. Clear skies complement the overall serene atmosphere.
Apartment in The Quarter
4.98 out of 5 average rating, 48 reviews

Thrush Nest View Studio Apartment

Forget your worries in this spacious and serene studio apartment designed for relaxation after a long day at the beach . Kick your feet up while enjoying a cup of coffee to the sunrise or a glass of wine to the sunset as this space provides panoramic views from every angle. Located in the centre of the island this vacation apartment is the ideal platform for exploring beaches, island tours and extraordinary dinning. Contemporary decor with modern amenities all can enjoy.

Top guest favourite
A private pool is surrounded by landscaped gardens, with a sun lounger positioned nearby. The pool's clear blue water reflects the bright sky and surrounding greenery, creating a serene outdoor space for relaxation.
Villa in Blowing Point
5 out of 5 average rating, 25 reviews

Modern Bungalow With Pool - 3 Min Walk To Beach

Immerse yourself in nature during your stay at The Bungalow, a tropical open-air villa perched amongst the trees on the island of Anguilla. Enjoy breath-taking ocean views from your private pool, take a quick walk down to the beach for a dip in Rendezvous Bay, and wind down while watching the sunset from your expansive roof deck. Nature lovers will delight in the property’s indoor-outdoor feel, surrounded by lush gardens and with visits from native birds.

Top guest favourite
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, 179 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 lounge chairs, garden furniture, outdoor table and BBQ * Office area * 100 Mbps Wi-Fi * 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, boutiques and other shops * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

Top guest favourite
Apartment in The Valley
4.97 out of 5 average rating, 38 reviews

Oceanfront Escape: Stunning Seaside Apartment

Escape to this freshly renovated, oceanfront 1-bedroom apartment which blends modern comfort with stunning sea views. The open-plan living space features large windows and a private balcony, perfect for enjoying ocean breezes. A sleek kitchen, cozy bedroom with a king-sized bed, and stylish bathroom provide everything you need for a relaxing stay. Located just steps from the ocean, this chic coastal retreat is ideal for a peaceful getaway.

Top guest favourite
An ice-filled bucket holds a bottle of wine in the foreground, while two elegant wine glasses sit in front. The backdrop displays a serene sunset with soft colors illuminating the sky, casting a warm glow over the surrounding greenery.
Condo in North Side
5 out of 5 average rating, 13 reviews

Island Escape w/ Private Firepit | Near Shoal Bay

Escape to your private retreat in North Side, Anguilla, just 10 minutes from stunning beaches. Designed for couples, this bright, modern 1-bedroom suite offers space to unwind and reconnect. Enjoy relaxed breakfasts in a full kitchen, movie nights in the open living area, and intimate evenings by the patio fire pit. After beach days, return to cool AC, plush bedding, fast WiFi, and a peaceful, beautifully maintained space made for two.

Guest favourite
Apartment in North Side
4.9 out of 5 average rating, 84 reviews

KC Corner House - (Car Rental available)

Kick back and relax in this newly renovated, calm, stylish space. This very tidy home at 1500 sq. ft. with modern décor/finishes, located in a quiet, peaceful and scenic area of Cedar Village, Northside. This abode is open to all. 8-10 minutes drive to St.James Medical School Campus. Only 5 minutes drive to Crocus Bay. Main supermarkets are all in 5 minute drive radius.

Superhost
Apartment in Bad Cox Pond
4.76 out of 5 average rating, 54 reviews

The Studio at AXA Farmhouse

Welcome to your tranquil retreat at AXA Farmhouse. This private studio offers a serene getaway, complete with a fully equipped kitchen, a spa-inspired bathroom, and a separate entrance for your convenience. Rest easy on a plush bed, and enjoy the comfort of air conditioning throughout your stay.

Guest favourite
A sunlit pool area features a crystalline infinity pool overlooking the ocean. Chaise lounges are arranged around the pool deck, complemented by tropical greenery. The modern guesthouse, with multiple levels, provides expansive views of the water and invites relaxation in a serene environment.
Cottage in Island Harbour
4.9 out of 5 average rating, 96 reviews

St.Somewhere Else

Oceanside guesthouse is peaceful, beautiful and gated. Full access to the bacce ball court, pool and ocean! We are located on the eastern end of the island, 5 minute drive to shoal bay and 3 minute drive to island harbor. Walking distance to some of the best local beach bars and restaurants!

Popular amenities for North Side vacation rentals

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  3. North Side