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Vacation rentals in Old Road Bluff

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Top-rated vacation rentals in Old Road Bluff

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

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Guest favourite
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, 55 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.

Home in Old Town
4.67 out of 5 average rating, 3 reviews

See Forever Villa

See Forever Villa: Your Tropical Sanctuary Breathtaking views of Soufriere Hills Volcano meet luxury living. Dive into a half-acre wellness haven with pool, gym, and fruit-laden trees. Coconuts and mangoes at your fingertips. Nearby beaches (Old Road, Isles Bay & Lime Kiln Bay), fine dining and local cuisines just moments away. More than a stay – an experience that reconnects you with nature's magnificent rhythm. Escape the ordinary. Embrace the extraordinary. Your volcanic paradise awaits.

Superhost
A spacious patio area is depicted, featuring a round glass dining table surrounded by four white wicker chairs. The view of the Caribbean Sea and distant islands is visible beyond the stone wall, framed by lush greenery and palm trees under a clear sky.
Home in Woodlands
5 out of 5 average rating, 3 reviews

Stylish Caribbean 3 Bdrm Villa Nestled in Nature

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.

Superhost
A serene courtyard is depicted featuring a swimming pool, framed by lush palm trees. A covered outdoor space is showcased, marked with 'VIP COURT YARD,' providing a tranquil setting as the sun sets in the background, creating a soft, colorful horizon.
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.

An outdoor patio area features a tranquil pool overlooking the ocean. Potted plants line the space, and spacious lounge chairs are positioned for relaxation. Scenic views of the sea and lush cliffs are visible in the background under a clear blue sky.
Villa in Old Town
4.89 out of 5 average rating, 9 reviews

Oceanfront Luxurious Villa Stunning Sunsets Avalon

Villa Avalon is a well appointed luxurious and rare ocean front property. All bedrooms boast a comfortable King size bed and private ensuite bathroom. The kitchen is well equipped with everything you will need. The main living is outdoors in this villa, with 180 degree ocean view as you lounge, dine or sunbathe. Enjoy beach and mountain view from the main patio and breathtaking mountain and volcano views from the lookout. This villa offers ocean front living at it's best.

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.

Guest favourite
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
A private pool is surrounded by a red-tiled deck, featuring two white lounge chairs. Lush greenery and palm trees frame the view of the Caribbean Sea in the distance, with blue skies overhead, creating a peaceful outdoor retreat.
Home in St Peter's Village
5 out of 5 average rating, 24 reviews

Providence: Paul McCartney's former hideaway

Providence Estate House, a unique historic Caribbean house, was the home of Paul McCartney and his family when he recorded "Tug of War" and "Ebony and Ivory" with Stevie Wonder in 1981. Originally built in 1918, it was rebuilt following 1989's Hurricane Hugo. Completely private, set in 10 acres on a breezy hilltop with sunset views overlooking the Caribbean from almost 600 feet, you will love the space, peace and serenity of this classical home and its beautiful setting.

A tranquil swimming pool is visible, surrounded by a tiled patio and lush greenery. Scenic views of the nearby beach and coastline can be seen in the background, under a clear blue sky. Palm trees add a tropical touch to this inviting outdoor space.
Home in Old Town
5 out of 5 average rating, 4 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, 13 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.

Guest favourite
A spacious swimming pool reflects the clear blue sky and creates a vibrant contrast with the surrounding coastal scenery. Palm trees are visible along the perimeter, providing a tropical ambiance. The pool deck features elegant stone paving, enhancing the outdoor space's natural beauty.
Villa in Woodlands
4.86 out of 5 average rating, 21 reviews

Oceanfront luxury, king bed,AC,WiFi,4beds,3bedroom

Private, gated luxury villa leaves Nothing between you and the Carribean blue sea. You can view turtles and dolphins from the comfort and privacy of your pool deck. You will never get tired of the sunsets and the moonlight views. Wake up to the sound of waves and birds every morning. Free WiFi, cable tv and fire stick. 5 minutes to 3 of the island’s premier restaurants, supermarkets, and the village rum bars.

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
4.81 out of 5 average rating, 32 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.

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