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Holiday rentals in Island Harbour

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Top-rated holiday rentals in Island Harbour

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Top Guest favourite
A serene beach view is captured, showcasing clear turquoise waters meeting powdery white sands. A picnic table sits on the beach, bordered by vibrant green plants and palm trees. Soft clouds drift above under a bright blue sky, completing the tranquil seaside scene.
Apartment in Simpson Bay
4.96 out of 5 average rating, 217 reviews

Lilly's Beach

This is a very SPECIAL SMAll RESIDENCE known as Ocean Edge . Beach Front located directly on beautiful Simpson Bay Beach! Enjoys one of the best locations on the island . Panoramic sea views with your toes in the sand and balmy Caribbean breezes. A clear turquoise sea dazzles in tropical sun, powdery white sands stretching along one of St. Maarten's longest beaches. Apartment with modern amenities and comforts. A perfect vacation spot ! Back up system installed to insure electricity.

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, 66 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
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, 180 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
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
4.97 out of 5 average rating, 39 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
Villa in Island Harbour
5 out of 5 average rating, 8 reviews

Villa Grande Downstairs Oceanview w/ Pool | 2BR

Villa Grande’s downstairs unit offers stunning ocean views, pool access, and island comfort in a spacious 2-bedroom, 2-bath villa. Enjoy a full kitchen, bright living area, and peaceful patio overlooking the sea. Located just minutes from Anguilla’s best beaches, restaurants, and nightlife, it’s ideal for couples, families, or friends looking for a relaxing Caribbean getaway with all the comforts of home.

Top Guest favourite
Loft in Grand Case
4.93 out of 5 average rating, 121 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.

Guest favourite
A beachfront terrace features modern white lounge chairs and a dining table, overlooking the crystal clear waters. A grill is positioned nearby, and a cooler rests beside an ice bucket, enhancing the inviting coastal experience.
Apartment in Sandy Ground
4.96 out of 5 average rating, 23 reviews

Luxury Beachfront Enclave Unit 2

Luxury brand new beachfront residence directly on beautiful Sandy Ground Beach. This spacious second 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.

Guest favourite
Aerial view of the property reveals colorful buildings along the shoreline, surrounded by lush greenery. A pool is visible in the foreground, while the turquoise waters of the Caribbean Sea gently lap against the rocks. Palm trees enhance the tropical setting.
Cottage in Island Harbour
4.87 out of 5 average rating, 62 reviews

Lush Garden Studio with Pool Access – Suite #3

Welcome to your peaceful island retreat! This charming 1-bedroom suite offers serene views of the lush tropical gardens. Start your morning with coffee on the balcony surrounded by greenery, or unwind in the evening with a glass of wine as you soak in the tranquil atmosphere. The suite is fully equipped with everything you need for a comfortable and unforgettable vacation!

Guest favourite
A covered outdoor patio features turquoise railings and a bench, offering views of the beach and sea. Lush green grass leads to the shoreline, with gentle waves lapping against the shore. The sky is bright with white clouds and ample sunlight.
Cottage in AI
5 out of 5 average rating, 13 reviews

Sea View Cottage, Spectacular Ocean View!

A true Caribbean feeling awaits you in our cozy 1200 square foot 2-bedroom cottage. This lovely beach side cottage offers a spacious covered outdoor patio area and a front patio that is ideal for relaxing while enjoying the stunning views of St Barth's and St. Martin. The traditional style cottage is ideal for a family getaway or a holiday with friends.

Guest favourite
A spacious living area is shown with large open doors leading to a private terrace. Light-colored furniture is arranged comfortably, with a dining table ready for meals. The ocean view is visible in the background, providing a serene backdrop to the inviting space.
Apartment in Grand Case
5 out of 5 average rating, 19 reviews

1 bd Grand-Case beach

Welcome to your perfect getaway in Grand Case, Saint Martin! This beautifully appointed 1-bedroom apartment offers stunning ocean views and is just steps away from the pristine beach. Whether you're here to relax, explore, or indulge in world-class cuisine, this location has everything you need.

Superhost
A bright sleeping area features a spacious bed with crisp white linens. A modern chair is positioned nearby, with light wood flooring extending across the room. A stylish bathroom is visible through an arched opening, showcasing a freestanding tub and a sleek shower.
Apartment in Bad Cox Pond
4.75 out of 5 average rating, 57 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 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, 97 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 Island Harbour holiday rentals