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Holiday houses in North Side

Find and book unique accommodation on Airbnb

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 kitchen features sleek black cabinetry and a large refrigerator. A ceiling fan provides airflow in the airy space. A small dining table is set for relaxation, while various kitchen appliances are arranged neatly on the countertops. Natural light enters through a window with light-filtering shades.
Home in North Side
5 out of 5 average rating, 35 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!

Guest favourite
Villa in Island Harbour
4.97 out of 5 average rating, 68 reviews

Oceanfront Villa Sleeps 6 | Private Pool & Hot Tub

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
An expansive terrace features a private pool and lounging area, offering unobstructed views of the serene blue ocean and nearby sailboats. The space is surrounded by greenery, creating a tranquil outdoor environment for relaxation.
Loft in Marigot
4.99 out of 5 average rating, 191 reviews

Sea Loft Vue imprenable - piscine privée

* Loft de 200m² * Vue mer exceptionnelle * Piscine privée * A 250 mètres de la petite plage de Galisbay * Terrasse avec chaises longues, salon de jardin, table d'extérieur et BBQ * Espace bureau * Wifi 100 Mbps * TV avec milliers de chaines du monde entier * A 250 m à pied de la marina Fort Louis de Marigot * A 5 min à pied du centre ville de Marigot avec ses restaurants, boutiques et autres commerces * A 5 min de l'embarcadère pour Saint-Barth et Anguilla, et de la station de taxis

Top Guest favourite
Home in Shoal Bay Village
5 out of 5 average rating, 79 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
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.
Apartment in The Valley
4.91 out of 5 average rating, 23 reviews

Modern 1BR Getaway *Car Rental Available*

Welcome to your cozy home away from home! This 1-bedroom apartment offers the perfect blend of comfort, style, and prime convenience—the ideal launching pad for exploring the island or unwinding in peace. ✨ Why you’ll love it: Warm, inviting, and beautifully designed to recharge after adventure. Fully equipped with modern amenities. 🚗 Exclusive Guest Perk: We offer a discounted car rental rate when bundled! Message us once reserved to secure your ride.

Top Guest favourite
Villa in Blowing Point
5 out of 5 average rating, 32 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.

Guest favourite
Home in AI
4.93 out of 5 average rating, 44 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
A shaded outdoor seating area features a curved, cushioned lounge chair positioned to face the ocean. Lush greenery surrounds the space, while the blue sky is dotted with fluffy clouds above. The calming sea is visible in the background, enhancing the serene atmosphere.
Apartment in The Valley
4.98 out of 5 average rating, 49 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
Home in North Side
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
Apartment in North Side
5 out of 5 average rating, 24 reviews

Island Suite with Private Fire Pit

Book your stay and the concierge handles Anguilla for you. Ferry coordination, rental car, restaurant reservations, and a welcome spread waiting when you arrive. All sorted before you land. ⭐ What guests say • “Better in person than the photos” • “No other host does all this” • “Would not stay anywhere else in Anguilla” Every single guest. Every single time. Five stars. Check availability before your dates go.

Top Guest favourite
Loft in Grand Case
4.94 out of 5 average rating, 136 reviews

Beachfront Loft in Grand Case - Sea View

An exceptional beachfront loft on Grand Case Beach, offering majestic ocean views and a prime position above the iconic Rainbow Café. In high season, a stylish and trendy atmosphere sets the tone until about 11 p.m. Sunbeds can be reserved either directly or through us—but guests who book with our help enjoy privileged touches. A luminous, sophisticated retreat steps from Grand Case’s finest venues.

Top Guest favourite
An outdoor area features a sleek infinity pool extending towards the Caribbean sea, surrounded by spacious tiled decking. A shaded seating area with sun loungers is positioned nearby, while lush greenery adds a vibrant backdrop. Large glass doors provide a seamless view into the interior living space.
Villa in Philipsburg
4.99 out of 5 average rating, 323 reviews

Villa Dream View Belair Sint Maarten SXM

Embrace the tranquility in a friendly tropical caribbean modern designed private villa with spacious rooms that are sure to keep you comfortable and feeling at home. Enjoy the sunny day with infinity pool overlooking caribbean sea or enjoy the sea view while watching the sailing huge cruise ships.

Popular amenities for North Side holiday rentals

  1. Airbnb
  2. Anguilla
  3. North Side