Holiday rentals in North Side

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Top-rated holiday rentals in North Side

Guests agree: these stays are highly rated for location, cleanliness and more.

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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, 30 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
A private pool is situated beside the ocean, surrounded by lounge chairs facing the water. The tranquil surface of the pool reflects the morning sunlight, while the Caribbean sea extends into the horizon, highlighting the serene atmosphere of the villa.
Villa in Island Harbour
4.96 out of 5 average rating, 50 reviews

Stunning Oceanfront Villa ~ Pool, Jacuzzi & Kayaks

Your 5 star Airbnb guest favorite oceanfront villa includes a private pool, hot tub and panoramic Caribbean views. Scilly Cay is right out front and only a 5 min drive to famous Shoal Bay. Wake up to the glowing turquoise sea from the master King Bed. Relax on the spacious lower & upper decks. Full kitchen, private office and outdoor shower. Enjoy kayaks, stand up paddleboards, additional club pool, decks & fire pit. Perfect for families or romantic getaway in paradise. Read our 5 star reviews!

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, 22 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
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, 55 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.

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
4.97 out of 5 average rating, 30 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.

Superhost
A stylish living area is showcased with a green accent wall. Two woven planters with decorative plants are positioned beside a coffee table made of natural materials. Soft curtains frame the windows, while a mounted television adds modern convenience to the space.
Flat in North Side
4.89 out of 5 average rating, 72 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.

Guest favourite
A spacious bed with a textured white coverlet is centered in the room, flanked by two nightstands with table lamps. A serene landscape painting is mounted above the bed. Natural light filters through the window, accentuated by white curtains.
Apartment in The Valley
5 out of 5 average rating, 8 reviews

Sunset Serenity.

Relax and unwind in this distinctive and serene retreat. Experience a calm and pleasant stay in my tranquil one-bedroom apartment during your visit to Anguilla. The unit is equipped with Wi-Fi, full air conditioning, a washing machine, a dryer, a balcony, a kitchen, and a dedicated workplace to provide a comfortable stay. We look forward to hosting you!

Top guest favourite
A modern living space features a cozy sectional sofa with decorative pillows, complemented by a coffee table. A kitchen area, equipped with a fridge, stove, and bar stools, is visible in the background. Light streams in through large windows, illuminating the blue accent wall.
Flat in Mount Fortune
4.98 out of 5 average rating, 58 reviews

Fortune Estate (Car rental available)

Newly built modern cozy apartment with remote gate access, back up generator and perimeter security camera system located in Mount Fortune on the eastern end of the island. Five minutes driving access to grocery stores, Island Harbour beach and the restaurants thereon like Falcon Nest. 10 minutes drive from the famous Shoal Bay beach.

Guest favourite
A well-organized bedroom features a spacious bed dressed in soft linens, complemented by a blue throw blanket. A mirrored wardrobe and shelves offer ample storage, while a reflective mirror enhances the room's openness. Soft gray walls create a calm and balanced atmosphere.
Flat in North Side
5 out of 5 average rating, 7 reviews

Jenna Ville Estate Unit 1-Cedar Haven Lower floor

Jenna Ville Estate offers a serene retreat for business or family travel. It provides a home-like ambiance, fresh local fruits when in season, and proximity to central shopping areas. Located less than 5 minutes from Crocus Bay, guests can enjoy its beautiful beach and nearby restaurants.

Guest favourite
A modern kitchen area features a bar-style countertop accented with a mosaic design. Two high stools provide seating, while stainless steel appliances, including a refrigerator, are visible. Green cabinetry and neutral-toned flooring contribute to a clean, functional space.
Guest suite in The Valley
4.95 out of 5 average rating, 43 reviews

Hidden Treasure

Hidden Treasure is a unique place with a style of its own. Everything comes to life when contrasted against its hues of green and brings a sense of home that is difficult to escape. From the centrality of location to the variety of amenities offered within, this is a definite win!

Guest favourite
A comfortable bedroom showcases a spacious bed adorned with white linens and decorative pillows. A wooden nightstand features a vase with fresh flowers and a selection of bottled beverages. Soft lighting is provided by a wall-mounted lamp.
Bungalow in Shoal Bay Village
4.97 out of 5 average rating, 38 reviews

1 Bd cottage, on Oceanfront Estate, Shoal Bay East

LaVanda at Bellamare Estate is a 1 bedroom property with living area, kitchen and patio. The suite offers seclusion in a setting of lush tropical gardens. Our Property Manager is available to answer questions.

Superhost
A cozy bedroom is equipped with a spacious bed adorned with a green throw blanket. Light-colored curtains frame the windows, complementing the neutral wall color. A sleek dresser and bedside tables provide storage, while a full-length mirror reflects the room's modern design.
Flat in The Valley
4.87 out of 5 average rating, 15 reviews

SYL Apartment *Beautiful & Spacious*

This newly built cozy one-bedroom apartment is the perfect choice for travelers seeking a comfortable and well-equipped home away from home.

Popular amenities for North Side holiday rentals

  1. Airbnb
  2. Anguilla
  3. North Side