Holiday houses in Isle's Bay Beach

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Top-rated holiday rentals in Isle's Bay Beach

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A private pool is featured next to a cottage, positioned on a hillside with panoramic views of the ocean and surrounding greenery. The outdoor area includes a lounge chair and is bordered by a white railing, contributing to the serene environment.
Guesthouse in Old Town
4.87 out of 5 average rating, 53 reviews

Blue Lime Cottage

Our cottage is located at a walking distance of Lime Kiln Beach. You will like our cottage because of its privacy and the nature surrounding it. As of October 1st Monserrat welcomes visitors who are fully vaccinated with a WHO approved vaccine and a negative Covid test done within the last 72 hours. In addition visitors are required to quarantine for 5 days upon arrival. During the quarantine you can walk around our property and use the swimming pool in addition. Items can be delivered to you.

Superhost
The exterior of the apartment is presented, featuring a vibrant yellow facade. A covered porch area is visible with green railings, providing an inviting entrance. Windows are fitted with shutters, and landscaped greenery lines the ground, enhancing the overall charm of the space.
Apartment in Barzeys
4.88 out of 5 average rating, 26 reviews

Lovely two bedroom apartment

Welcome to your Caribbean bolthole. This is a lovely two bedroom apartment set in the hills of beautiful Montserrat. The apartment is set on the edge of a valley (Ghaut ) with unblocked views of the sea towards Redonda and Nevis and a cool breeze in the evenings. You will have exclusive use of our apartment, with a separate entrance for you to come and go at your leisure. The Host lives in the apartment above, and will therefore be on hand by phone or email if you run into any difficulties.

Superhost
The exterior of the villa is framed by lush tropical landscaping, featuring vibrant green plants and colorful flowers. A paved driveway leads up to the entrance, where the two-story white building is highlighted under a clear blue sky.
Home in Woodlands

NEW Stylish Caribbean 3 Bdrm Villa

This incredible 3 bedroom Villa's garden grounds stretches over 100 yards of unobstructed panoramic views, abundant in colour with blooming florals and lush with towering mahogany trees under which hammocks swing in the ever present view of the Caribbean Sea. From corner to corner, this estate has one of the most beautiful, vistas with the sound of waves lapping on its shoreline below -plus views of neighbouring islands Nevis, Redonda & the tip of St. Kitt's - a constant reminder of paradise.

A scenic view is presented from a balcony, featuring a railing with decorative balusters. The horizon shows a blend of blue sky and clouds above verdant hills, while the distant ocean is faintly visible, creating a serene backdrop.
Cottage in Saint John's
5 out of 5 average rating, 3 reviews

PeacefulCottage MNI

This Chic, stylish & centrally located cottage is perfect for couples and solo travelers seeking a peaceful island getaway or a well-deserved retreat. Designed for relaxation and comfort, the space offers a calm, private atmosphere ideal for unwinding after a day of exploring Montserrat. With reliable Wi-Fi and a quiet, inspiring environment, the cottage is also well suited for remote workers and digital nomads looking to focus, recharge, and complete projects away from the office.

An outdoor pool surrounded by a sun deck is depicted, featuring lounge chairs and tropical plants. The scene overlooks the Caribbean Sea with distant islands visible on the horizon. A clear sky complements the serene ambiance.
Villa in Woodlands
4.85 out of 5 average rating, 26 reviews

Secluded Caribbean retreat with a spectacular view

Nestled in Montserrat's rainforest-covered hills, with breathtaking views over the Caribbean Sea and a ten-minute walk to an often-deserted beach, this secluded hideaway is perfect for those seeking a restorative and utterly peaceful vacation. Because it is west-facing, sunset cocktails on either of the 60ft balconies or pool deck are a must. I can send a drone video of the villa and garden (kindly sent to me by a guest) once a booking has been made and email addresses exchanged.

A spacious patio is viewed from a table and chairs, oriented towards a pool and lush greenery. The ocean can be seen in the distance, with mountains framing the landscape. Natural light highlights the vibrant colors of the outdoor furnishings.
Home in Old Town
5 out of 5 average rating, 3 reviews

Bananaquit at the beach!

Wishing to escape to a delightful villa overlooking a lovely beach on the most tranquil island ever? Planning to spend hours poolside soaking up the sun or just taking cool dips? Want to be footsteps from the shores? Bananaquit says yes to all above! This comfy villa in a prime location on Montserrat has stunning views all around. The villa includes 2 bedrooms upstairs and a lower level 1 bedroom apartment. Lush mature gardens surround this perfect getaway! Book Now!

Top Guest favourite
A doorway frames a scenic view of the sea and coastline, with gentle waves lapping against the shore. A wooden deck is visible, inviting guests to enjoy the outdoors. The light blue sky features wispy clouds, enhancing the coastal ambiance.
Guesthouse in Little Bay
5 out of 5 average rating, 8 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.

A sunset view is captured over the ocean, with warm hues illuminating the sky. The villa's exterior is framed by lush greenery and pink bougainvillea flowers. The pool is visible in the foreground, reflecting the evening light.
Home in Woodlands
5 out of 5 average rating, 4 reviews

Oasis Villa

Oasis is a beautiful secluded caribbean villa, built in a lush green garden in woodlands, Montserrat. Its a two bedroom villa with two bathrooms. Master suite is steps away from pool , laundry room, kitchen, dining room, living room, large porch overlooking the ocean, garden and a forty foot swimming pool. Oasis is also approximately a ten minute walk to the beautiful, picture perfect and secluded woodlands beach.

Guest favourite
Apartment in Saint Peter's
4.92 out of 5 average rating, 36 reviews

Lucy's Sunny Villa Studios ll

Take an early evening stroll to Bunkum Bay and enjoy the Sunset in the warmth of the Caribbean sea, we are ideally placed for those with a fondness for nature a perfect place to stay for couples. This spacious studio apartment will also accommodate up to 3 adults if required, with all modern amenities stylish shower room and furnishings, Come kickback and relax with us at any one of Lucy's Sunny Villa Studios

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Apartment in Cudjoe Head
4.75 out of 5 average rating, 16 reviews

Cozy Apartment w/ Jeep & Prime Locatio

The VIP Queen Suite is a fully furnished private unit in a prime location, featuring a queen-size bed, kitchenette, living area, and optional AC -US$15 per day). Located on the ground floor of VIP Penthouse & Suites, guests enjoy full access to a courtyard with a pool and dining area. Walking distance to supermarket, pharmacy, restaurants, bars & more. Jeep rental available at an additional cost.

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.

A spacious pool deck features a clear blue swimming pool surrounded by several lounge chairs. Lush greenery and ocean views are visible in the background, while the sunlight reflects off the water's surface, creating a tranquil outdoor space.
Villa in Garibaldi Hill
4.7 out of 5 average rating, 27 reviews

Isles Bay Villa

Exclusive three bedroom villa overlooking the Belham Valley and Old Road Bay. Our villa overlooks the beach where Hank's Beach Bar is located. You can see and hear the waves breaking on the beach from the pool deck. You’ll love the views, the private location, and the trade winds cooling the house. Our villa is perfect for up to three couples or a family vacation.

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