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Holiday rentals in Little Harbour

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Top-rated holiday rentals in Little Harbour

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

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Top guest favourite
A bright terrace dining area features a large white table surrounded by six chairs. A Weber grill is positioned nearby, and stunning views of the turquoise sea and anchored boats are visible through expansive glass walls, allowing natural light to fill the space.
Flat in Sandy Ground
5 out of 5 average rating, 38 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

Guest favourite
A covered terrace features comfortable seating arrangements with light-colored cushions, facing a private lap pool. Sun loungers are placed in a row beside the pool, shaded by large turquoise umbrellas. Lush greenery and ocean views create a serene outdoor setting.
Home in Little Harbour
5 out of 5 average rating, 5 reviews

Charming 4 Bedroom Estate w/ Beach Access

Tigh-na-Mara Villa, exudes old world West Indies charm inside and out. This storybook island villa immerses you in a delightful ambiance of days gone by, combined with modern necessities including high speed internet, a recently renovated chef’s kitchen and air-conditioning throughout. The sparkling lap pool is your own private paradise — and you have direct access (via a 2 min path) to Elsie Bay Cove. This unique Villa is nestled in lush landscaping with magnificent views of St. Martin.

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
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
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.
Flat 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.

Top guest favourite
A modern two-story building features a sleek white exterior, surrounded by landscaped grounds and neatly arranged gravel pathways. Balconies can be seen on both levels, offering outdoor seating. Lush greenery and palm plants are visible in the foreground, contributing to the serene environment.
Apartment in Lower South Hill
5 out of 5 average rating, 34 reviews

Spacious 2nd FL Studio - 3 min to Rendezvous Bay

Immerse yourself at Merrivale Residence – your stylish island escape! This modern, oversized studio is just a 3-mins from Rendezvous Bay Beach. Ideal for couples, solo travelers or digital nomads and features a sleek workstation, private patio, generous walk-in closet, fully equipped kitchen, washer/dryer, Wi-Fi, Netflix and central A/C. Enjoy comfort, tranquility, and convenience all in one perfect location.

Top guest favourite
Loft
4.94 out of 5 average rating, 134 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
Apartment in Swing High
5 out of 5 average rating, 14 reviews

Deany's Uptop Luxury Suite 6

Enjoy the lucious island breeze and admire Anguilla's sensational view at Deany’s UpTop Luxury Suite. This short-term rental property provides high-quality, private accommodation in a desirable location in Anguilla. This recently upgraded apartment offers the ultimate blend of comfort and elegance, making it perfect for couples, friends, or private getaways.

Top guest favourite
A view of the house from the side shows vibrant green shutters and a landscaped area featuring indigenous plants. In the background, a sandy pathway leads to the beach, where boats can be seen on calm turquoise waters under a sunny sky.
Home in Sandy Ground
5 out of 5 average rating, 25 reviews

Rehenita’s Abode

Forget your worries in this house. It is surrounded with indigenous plants, palms and coconut trees. Located in Sandy Ground Village. A few more steps you are on the beach which features a slew of famous and delicious beach restaurants and bars. You can also go snorkeling along the reefs or enjoy the sunset while walking on the beach.

Top guest favourite
A spacious outdoor living area is framed by elegant pillars, showcasing stunning views of the tranquil Caribbean Sea. Comfortable seating is arranged for relaxation, while the distant silhouette of a nearby island adds to the serene coastal ambience.
Townhouse in Sint Maarten
4.98 out of 5 average rating, 103 reviews

Indigo Bay Villa Poolside - Ocean 14

Experience refined Caribbean living in this enchanting 2-bedroom villa, nestled within the exclusive Indigo Bay community of St. Maarten. This beautifully designed villa offers a perfect blend of comfort, style, and outdoor elegance, making it an ideal retreat for those seeking tranquility and luxury.

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.

Guest favourite
A sunlit pool area features a crystalline infinity pool overlooking the ocean. Chaise lounges are arranged around the pool deck, complemented by tropical greenery. The modern guesthouse, with multiple levels, provides expansive views of the water and invites relaxation in a serene environment.
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!

Top guest favourite
Flat in West End
5 out of 5 average rating, 81 reviews

Creative Suite: Modern Studio Unit

This newly beautiful vacation home is perfectly built with a view of Sint Maarten that is sure to take your breath away.

Popular amenities for Little Harbour holiday rentals