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Holiday rentals in North Side

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Top-rated holiday 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, 34 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!

Top guest favourite
A spacious living area features large windows offering stunning ocean views. Neutral-toned furniture, including a white sectional sofa and wood coffee tables, creates a relaxed environment. A ceiling fan and stylish light fixtures are present, and a dining space with modern appliances is visible in the background.
Flat in Sandy Ground
5 out of 5 average rating, 33 reviews

Enclave 3 Luxury Beachfront Penthouse

Luxury brand new beachfront penthouse directly on beautiful Sandy Ground Beach. This spacious third floor unit is 1,684 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, Tempur-pedic mattresses, and much more

Top guest favourite
A serene beach scene features soft white sand gently sloping towards calm turquoise waters. The sky is bright blue with a few scattered clouds, creating a sense of openness and tranquility. The horizon line blends seamlessly with the ocean, inviting relaxation.
Home in Shoal Bay Village
5 out of 5 average rating, 75 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.
Flat in The Quarter
4.98 out of 5 average rating, 49 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.

Guest favourite
Flat in George Hill
4.96 out of 5 average rating, 26 reviews

Boutique 2-BR Suite Apartment CARTeas|Anguilla

CARTeas is a spacious two-bedroom boutique apartment located in the quiet village of George Hill, Anguilla. Situated on the upper level with a private entrance and keyless entry, the apartment offers a peaceful retreat with modern comforts. Enjoy a king-bed primary suite with soaking tub and walk-in shower, a queen guest suite with walk-in shower, full kitchen, living area, desk nook, TVs, and in-unit washer and dryer. A cozy Caribbean stay designed to feel like home.

Guest favourite
An aerial view of the villa showcases its modern architecture with a terracotta-tiled roof and expansive outdoor spaces. A large infinity pool reflects the surroundings, while shaded areas with loungers and a fire pit area provide spaces for relaxation and gathering.
Villa in Upper Prince's Quarter
4.95 out of 5 average rating, 118 reviews

The Blue Door Villa - 4 bed ocean view home

At the Blue Door Villa, we offer our guests all the creature comforts of being in a well-equipped vacation home. We are located on the Dutch side, minutes from the French border in a quiet gated community. The Blue Door Villa is a perfect place to relax while you listen to ocean waves and swim in the infinity pool. There are multiple outdoor spaces offering privacy or space to gather. We are now offering our guests an exclusive, free concierge service.

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
4.99 out of 5 average rating, 186 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

Guest favourite
This bedroom features a spacious bed with a light comforter and decorative pillows. Two bedside lamps are positioned on either side, and large windows with light blue curtains allow natural light to fill the room. Coastal artwork adds a serene touch.
Home in AI
4.95 out of 5 average rating, 43 reviews

Villa Cool Serenity

This modern three-bedroom, two-bathroom home with a private office in a quiet neighborhood 5 minutes from Crocus Bay has the perfect, spacious environment for a group of family or friends. You'll have the entire home to yourself. The villa can accommodate groups of up to 11 guests and is within driving distance from most beaches and restaurants in Anguilla. The home has a full kitchen, air conditioning, and essentials to make your stay comfortable.

Top guest favourite
An open-plan living area features a light-colored sofa with decorative pillows and a round coffee table. Large windows provide expansive views of the ocean and natural light. A few plants are positioned throughout, and access to the balcony is visible in the background.
Flat in The Valley
4.98 out of 5 average rating, 46 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.

Superhost
A welcoming sign and decorative plant are visible in the loft area. Wooden stairs lead upward, showcasing the natural texture of the wood. The sign emphasizes connection and positivity, contributing to an inviting atmosphere.
Home
5 out of 5 average rating, 8 reviews

3 Level Loft Apartment

Welcome to my beautiful three-bedroom apartment in Anguilla! This spacious and modern home is perfect for a relaxing vacation. Located in a quiet area just moments from the pristine beaches, and all the best amenities. The apartment features a fully equipped kitchen, a washer and dryer, and a sprawling living room designed for relaxation, complete with a large TV for your entertainment. I hope you enjoy your stay in my home!

Top guest favourite
A spacious living area features two comfortable sofas adorned with decorative cushions, set against a backdrop of light-colored walls. Natural light fills the space through large windows, complemented by soft curtains. A modern dining area with gray chairs and a fully equipped kitchen is visible in the background.
Flat in North Side
5 out of 5 average rating, 21 reviews

Spacious Island Retreat with Backyard Fire Pit

Slow down, sink in, and savor island life just 10 minutes from Anguilla’s pristine beaches. • Cloud-soft queen bed with crisp hotel linens • Fresh pastries on your first morning • Roast marshmallows under the stars • AC and high-speed Wi-Fi • Private patio with fire pit & breezes • Concierge: massages, dinner, and more Smart TV, in-unit washer/dryer; just arrive. We’ll handle the rest.

Guest favourite
A serene outdoor space is featured with two comfortable chairs positioned around a table. The infinity pool extends towards the ocean, with vibrant blue water reflecting the sky. Lush potted plants are placed nearby, enhancing the coastal atmosphere.
Cottage in Island Harbour
4.9 out of 5 average rating, 102 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 holiday rentals

  1. Airbnb
  2. Anguilla
  3. North Side