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Vacation rentals in North Side

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Top-rated vacation rentals in North Side

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

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Top guest favorite
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!

Top guest favorite
Condo in North Side
5 out of 5 average rating, 12 reviews

10 mins to Beach | Concierge | Firepit w/ S’mores

Our newly refreshed 1-bedroom hideaway puts you 10 quick minutes from sun-kissed sand. Queen bed with hotel-quality linens Complimentary pastries your first morning Complimentary S’mores experience High-speed Wi-Fi & AC Private patio with fire pit for sunset s’mores Concierge Services; reservations, in-room massages & more are one message away. Smart TV for streaming nights in Washer/dryer inside the unit Book now and our team will handle the details so you can simply arrive and unwind!

Top guest favorite
Large glass sliding doors open to a sunny outdoor deck with views of the turquoise ocean. Comfortable lounge chairs and a dining table are visible among tropical palm trees. The living area features a soft gray couch and a wall-mounted TV, creating an inviting indoor space.
Apartment in Simpson Bay
5 out of 5 average rating, 220 reviews

The Beach House Apartment

A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more

Top guest favorite
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.

Top guest favorite
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, 41 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 favorite
An aerial view captures a pool area surrounded by palm trees and colorful buildings. Sun loungers are arranged near the pool, with guests enjoying the water. The ocean extends in the background, meeting a rocky shore under a clear sky.
Cottage in Island Harbour
4.97 out of 5 average rating, 29 reviews

Cozy Garden Studio with Pool – Suite #1

Property Summary: Relax in your inviting garden-view studio at Arawak Beach Club, featuring a unique bar area perfect for morning coffee or evening cocktails. Enjoy lush tropical surroundings from your private deck, a fully equipped kitchen, and cozy living space. Stay connected with high-speed fiber internet, cool off with air conditioning, or lounge by the pool with sunbeds. Complimentary kayaks and stand-up paddleboards (SUPs) are ready for your island adventures!

Guest favorite
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.
Apartment in The Valley
4.96 out of 5 average rating, 28 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 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.
Apartment 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 favorite
A spacious bedroom features a large bed adorned with soft white bedding and decorative blue pillows. A mirrored wardrobe and a wooden dresser are present, accompanied by hanging space along the wall. Natural light enters through window treatments that complement the room's soft blue tones.
Apartment in North Side
5 out of 5 average rating, 10 reviews

Jenna Ville Estate Unit 2 - Gardenia Upper 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 favorite
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, 42 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 favorite
A well-equipped kitchen features warm wood cabinetry and modern appliances, including a black refrigerator and microwave. Vibrant cookware is neatly organized on the countertop, while pops of color are added by multi-colored canisters. Natural light fills the space, enhancing its welcoming ambiance.
Apartment in The Valley
4.93 out of 5 average rating, 76 reviews

Fully Equipped Island Apartment with Fruit Garden

Live out your island adventures at this cozy apartment. Unwind at this comfortable one bedroom. Enjoy the privacy of this home with the convenience of being located just 7-minute walk from local supermarket, Ashley and sons. The area feels peaceful and secluded.

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.
Apartment in The Valley
4.86 out of 5 average rating, 14 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 vacation rentals

  1. Airbnb
  2. Anguilla
  3. North Side