Holiday houses in Lookout

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Top-rated holiday rentals in Lookout

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Guest favourite
An aerial view displays a spacious outdoor deck featuring lounge chairs and a central seating area, surrounded by lush greenery. A boat dock is visible, alongside calm waters reflecting the vibrant surroundings. The layout promotes relaxation and scenic views of the waterfront.
Apartment in Jolly Harbour
4.92 out of 5 average rating, 26 reviews

Stella Vista - Luxury Jolly Harbour Condo

Nestled on the north finger in Jolly Harbour, sits this amazing newly renovated waterfront villa. Stella Vista boasts scenic views of the mountain range, Harbour Island and is ideally located within walking distance to the North Beach. Jolly Harbour is a gated community with 24 hour security, 2 beaches, restaurants, hair salon, supermarket and countless other amenities to make your holiday stress free. Included with your stay is an electric golf cart for added convenience. Adults Only. No kids.

Guest favourite
The image features a wooden deck with two lounge chairs positioned for relaxation. A cabin with wooden shingles and wide steps leads into the greenery. Large windows and balcony railing provide a panoramic view of the surrounding trees and natural landscape.
Cabin in Sawcolts Village
4.98 out of 5 average rating, 169 reviews

Tranquil Farm - Secluded Woodland Eco Cabin

The wooden shingled cabin is totally off the grid. To reach the cabin is a short walk up through a small wood on a narrow winding path from the parking area. Built on stilts the cabin over looks farmland and woods with a long view down the valley to the hills of English Harbour. The cabin has a large bedroom with wooden four poster bed with mosquito net. Barn doors open onto a side balcony, an open air bathroom with rain water shower heated by solar and a full kitchen. Wonderful night skies.

Top Guest favourite
Apartment in Jolly Harbour
5 out of 5 average rating, 9 reviews

Wadadli Breeze - Laid back island elegance

Escape to Wadadli Breeze, a stunning waterfront villa on Jolly Harbour's North Finger. This 2-bed, 2.5-bath retreat blends modern luxury with Caribbean charm. Enjoy two terraces with marina views and seamless indoor-outdoor living. Optional concierge services, a captained boat at your private dock (for charter), and a golf cart (for rent) enhance your stay. Minutes from white-sand beaches, dining, a market, tennis, golf, and fitness facilities, Wadadli Breeze is your refined island gateway.

Superhost
A master bedroom features warm yellow walls and an inviting atmosphere. A spacious bed is adorned with neutral linens, complemented by decorative pillows. A large window offers a view of the outside, while wooden furniture adds a touch of elegance to the room.
Apartment in Cudjoe Head
4.91 out of 5 average rating, 11 reviews

Luxurious Penthouse w/ Breathtaking Views & Jeep

Experience the simple luxuries in life in a place that is simply extraordinary. Affordable & luxurious, VIP Penthouse & Suites is one of its kind sitting approx. 900ft above sea level on the hillsides of Baker Hill, Montserrat, WI. We are just 7 minutes away from the airport. Well-kept gardens, sparkling pool, outdoor kitchen w/ dining area & charming pergola. Close to the local bank, pharmacy, supermarket, restaurant/ bars, beauty salon. Jeep rental is available and we also arrange tours.

Top Guest favourite
The exterior of a charming cottage is framed by vibrant red and pink flowers. A covered balcony extends from the white structure, surrounded by lush greenery. A certification sign indicating adherence to COVID-19 protocols is displayed prominently.
Cottage in Saint Mary
4.96 out of 5 average rating, 105 reviews

Sweet Lime Beachside Cottage

!!COVID INSPECTED, CERTIFIED & OPEN!! Agave Landings are affordable, one and two bedroom apartments and a studio cottage less than 165 yards from one of Antigua's best beaches. Located on Antigua’s Southwest coast, they are within minutes of a variety of restaurants, shopping, and entertainment facilities; while allowing easy access to St. Johns, Betty's Hope, English Harbour, and other sites; and providing a relaxing retreat to end your day with beautiful sunsets and star-filled skies.

Top Guest favourite
A private patio area is accessed through glass double doors, shaded by a sail awning. Potted flowers in vibrant colors frame the entrance, complemented by a small dining table and chairs, creating a welcoming outdoor space.
Home in Crabbe Hill Village
5 out of 5 average rating, 47 reviews

Peaceful Village Beach Apartment

Immerse in the natural beauty of a local Caribbean village just 1-2 minutes walk from Crabbe Hill Beach, one of the best beaches in Antigua. Private double doors take you into a downstairs open plan studio with a fully equipped kitchen, double bed, shower room and A/C. Enjoy a glass of wine and sunset from the patio with a day bed and BBQ. Beach loungers and umbrellas at Crabbe Hill Beach Rentals are also included. Perfect for a creative retreat, solo traveller or romantic getaway.

Guest favourite
An outdoor deck area features a dining table with white chairs and two loungers positioned beside a private plunge pool. An entrance leads into a light-filled indoor space, complemented by greenery from surrounding trees.
Home in Valley Church
4.9 out of 5 average rating, 113 reviews

Shell Cottage with plunge pool, near the beach

On route to your temporary home, you will glimpse authentic Caribbean living. Traveling through small villages you will notice colorful chattel homes before arriving at your relaxing retreat. Sugar Fields Holiday Home is perfect for chilling. We are confident that you will enjoy your air-conditioned bedrooms, with private balconies and cozy, open plan indoor, outdoor living space. Please Note: This home is intentionally designed for adult occupancy only. 12 years & over.

Guest favourite
An outdoor deck features two lounge chairs with cushions, a small table adorned with potted plants, and a pitcher beside glasses. The setting is illuminated by a warm sunset, creating a serene ambiance over the water.
Townhouse in Jolly Harbour
4.92 out of 5 average rating, 126 reviews

Waterfront Villa – Designer Tropical Getaway

Townhome with 2 bedrooms, 2.5 bathrooms, 1200 sq. feet (111 sq. meters). Water facing private deck and 2 balconies with western sunset views. Fully stocked and equipped kitchen. On-site private parking for smaller cars; parking for larger vehicles a few steps away. Gated community with restaurants, bars and cafes, golf course, marina, supermarket, banks and rental car agencies. 10-minute walk to North Beach and golf course, 20-minute walk to restaurants, shops, other amenities.

Guest favourite
A villa is set amidst lush greenery, with palm trees surrounding its edges. The house features a light-colored exterior and a sloped roof. Large windows invite natural light, creating a connection with the tropical environment.
Villa in Saint Peter's
5 out of 5 average rating, 9 reviews

Lucy's Sunshine Villa Palm Loop, 3 Bed 2 bathroom

Bring the whole family over, with lots of room for fun & Surrounded by nature this villa is approximately ten minute walk to the closest beach. this villa offers the best for both worlds for the sea lovers or for those who prefer to simply relax at home on the veranda and take in the warm sunshine and take in beautiful Sunsets the Caribbean offers? then this is sure to meet your holiday needs. As a self-catering villa, you'll find all the amenities needed for a perfect stay.

Top Guest favourite
The cozy clubhouse is situated close to the shoreline and surrounded by lush palm trees. The structure features a porch with seating, offering views of the beach and the nearby rocks. A gentle slope leads from the clubhouse to the water, integrating nature with the living space.
Guesthouse in Little Bay
5 out of 5 average rating, 11 reviews

The Clubhouse

Welcome to Montserrat's first eco-conscious clubhouse by the sea. We are located on the northwest coast of our small but incredible island, in the centre of the Little Bay, steps away from the surf. We are only five minutes drive from the the new town “ brades’ , and just 3 mins walk to Marine Village, a collection of small bars, a couple restaurants an a dive shop. The Clubhouse is nestled between coconut trees in the heart of our beach community.

Superhost
Villa in Ffreye's Estate
4.84 out of 5 average rating, 103 reviews

Pool views meet the sea at Starfish House

Starfish House is the perfect getaway spot offering the most stunning, unobstructed views of the Caribbean Sea and Valley Church Beach on the west coast of Antigua. The ocean views can be seen from the entire property. Decorated with stylish tropical furnishings and accents, Starfish offers a laid back and relaxing atmosphere to totally unwind in. There is a lot of natural light flowing through the entire house making it bright as well as airy.

Superhost
A covered terrace features a colorful hammock and a small round table with two chairs. The view of the Caribbean Sea is prominent in the background, framed by lush greenery and rolling hills, providing a serene setting for relaxation.
Apartment in Old Town
4.8 out of 5 average rating, 30 reviews

Lime Cliff

Ideally located in the quiet area of Old Town, overlooking the caribbean sea, this newly nuilt house is at a walking distance from Lime Kiln Beach. You can enjoy the cool breeze and the great view on the Centre Hills, the cliffs and the sea, while liming in the hammock on the covered terrace ! You will have access to the neighbour pool, owned by the family and serving 3 independent buildings.

Popular amenities for Lookout holiday rentals

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