Montserrat vacation rentals

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Top-rated vacation rentals in Montserrat

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Guest favorite

A balcony overlooks a scenic view with soft hues from a setting sun. Two white chairs and a small table create a cozy seating area, framed by blue walls and white railings, enhancing the connection to the surrounding natural landscape.

Guesthouse in Old Town

4.88 out of 5 average rating, 51 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

A private pool area is showcased with two inviting pools, surrounded by a sun deck. Patios and tables are arranged for outdoor seating, while lush greenery adds natural beauty. The expansive view reveals the Caribbean Sea and distant mountains under a partly cloudy sky.

Home in Saint Peter's

Caribbean Island Getaway

11,000 sq ft Villa nestled on 1.5 lush acres with the Caribbean Sea in your back yard and Mountains of Montserrat in your front yard . Relax in the private pool or walk in the gardens while enjoying the fruits from the many trees on the property when in season. Conveniently located to several restaurants and beaches .10 min hike or 4 min drive to Woodlands beach . Dine in the indoor or outdoor dining area .Watch the sunset from several different patios. This is how the Caribbean used to be.

Superhost

The image displays a vibrant scene of a tropical landscape, featuring a tall palm tree with golden fronds swaying gently. Bright yellow flowers bloom among lush greenery, while the view reveals the distant sea meeting the sky, illuminated by scattered clouds.

Apartment in Barzeys

4.88 out of 5 average rating, 25 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

An expansive ocean view captures two distant islands under a backdrop of soft, fluffy clouds. The calm water mirrors the sky's blue hues, creating a serene atmosphere. The foreground is gently framed by lush greenery, enhancing the sense of natural beauty and tranquility.

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 stunning view of the ocean is visible from the pool area, with clear blue waters stretching to the horizon. Lush greenery borders the scene, adding to the tranquil atmosphere. The bright sky features soft clouds, enhancing the sense of openness.

Home in Garibaldi Hill

5 out of 5 average rating, 4 reviews

Beautiful Caribbean Villa with spectacular views

Ranked one of the safest Islands in the Caribbean, Montserrat is a hidden gem of the Caribbean, where emerald hills cascade to pristine beaches. Montserrat beckons adventurers & serenity seekers alike to uncover its enchanting beauty. Dive into azure waters, explore volcanic landscapes, & immerse in vibrant local culture. This 3 bedroom private villa offers breath taking views of the sea, the valley & Volcano. The Villa is beautifully furnished, features great dining areas & a stunning pool.

A silhouette of a palm tree stands prominently against the backdrop of a vibrant sunset, with hues of orange and blue reflecting over the calm Caribbean Sea. The outline of lush greenery frames the scene, creating a serene and tranquil atmosphere.

Villa in Woodlands

4.83 out of 5 average rating, 23 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.

Superhost

A tranquil swimming pool reflects the colors of the sunset sky, framed by the surrounding lush vegetation. The spacious deck features wooden railings, providing an inviting area for relaxation. The adjacent bungalow is visible, with large windows allowing for ample natural light.

Home in Woodlands

4.9 out of 5 average rating, 10 reviews

Family Beachside Living with Oceanviews & Pool

Pristine Caribbean beaches, lush palm trees, and exhilarating island breezes await at this gorgeous 3-bedroom, 3-bath Montserrat stay. The bungalow is nestled in the secluded paradise of the West Indies, offering unbeatable panoramic views of Woodlands Bay and is just steps to the yellow sands of Woodlands Beach. Endless adventure awaits on this heavenly island, where you can explore volcanoes, tropical rainforest hiking trails, and local restaurants, all within arm's reach!

Top guest favorite

A tall palm tree stands against a vibrant sunset, silhouetted against the vast Caribbean Sea. The horizon features distant islands, while the sky displays hues of orange, yellow, and soft blue, reflecting a tranquil evening atmosphere.

Home in St Peter's Village

5 out of 5 average rating, 17 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.

Guest favorite

Apartment in Davy Hill

5 out of 5 average rating, 24 reviews

RELAX-IN: 2-bedroom apartment w/ Jeep rental svcs

Our property is conveniently located close to all essential amenities. We offer a complimentary airport/seaport pickup service. Within a 2-3 minute walk, you can find major supermarkets, cookshops, bars, variety stores, and salons. The beach is just a 10-minute walk away. We provide Wifi and other amenities for a comfortable stay. We can arrange local tours, hiking tours, and taxi services on your behalf. A rental Jeep is also available at an extra cost.

Guest favorite

A tranquil scene featuring a shimmering pool reflecting the colors of the sunset. Lush palm trees are visible at the pool's edge, while the calm sea and colorful clouds create a serene backdrop.

Villa in Woodlands

4.94 out of 5 average rating, 17 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.

Top guest favorite

A panoramic view captures the lush green hills and coastline of a Caribbean island. The land is gently sloping toward the ocean, reflecting soft golden tones under a partly cloudy sky, creating an inviting natural landscape.

Apartment in Saint Peter's

4.95 out of 5 average rating, 21 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

Superhost

A serene pool area overlooks the expansive Caribbean Sea, with gentle waves visible in the distance. A bright turquoise chair is positioned nearby, inviting relaxation. Lush greenery borders the space, and the sky is adorned with scattered clouds, enhancing the tranquil atmosphere.

Apartment in Old Town

4.79 out of 5 average rating, 29 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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Popular amenities for Montserrat vacation rentals

Laptop-friendly workspace

Other great vacation rentals in Montserrat

A large outdoor pool glistens under the sun, surrounded by a tiled deck and lush greenery. Beyond the pool, a stunning view of the Caribbean Sea and sky is visible, with distant islands faintly outlined on the horizon.

Villa in Garibaldi Hill

4.14 out of 5 average rating, 7 reviews

4BR Villa with Breathtaking View and Pool

TaraRating, 5 stars26 months ago

you need to be prepared to be self sufficient in Montserrat especially in Isles Bay which is beautiful. Some things are hard to come by and expensive but that is due to the circumstances of life on the island. Beautiful and clean and unspoiled.

A close-up of a hearty breakfast plate featuring scrambled eggs, baked beans in a small dish, crispy bacon, and sausage links. Toast is visible in the background, alongside additional plates with varied dishes, suggesting a fulfilling morning meal.

Villa in Cudjoehead

PARADISE VILLA

WinstonRating, 5 stars26 months ago

Scenic location . Certainly stay here again. Excellent host

Guesthouse in Saint Peter Parish

Aariyah Bellè Villa

SadéRating, 5 stars2 months ago

We really enjoyed our stay here, and the host was very accommodating in making our stay great! The home was modern, well-equipped, and in a good location, which was helpful. The grounds and scenery were also beautiful!

A serene pool area is seen with several lounge chairs arranged around a captivating blue pool. Palm trees provide shade, and a distant view of the water creates a calming backdrop, enhancing the outdoor relaxation space.

Hotel room in Old Road Bluff

5 out of 5 average rating, 3 reviews

The Vue Pointe Hotel

LeifRating, 5 stars8 months ago

We had a great stay. The view on the Volcano is amazing. Also we had a very nice seaview. The cottage is big and pretty and we found everything we needed. Communication with host was quick he provided us with very helpful information. We very much recommend this beautiful place

Home in Saint John's

4.2 out of 5 average rating, 10 reviews

Comfy & modern 3 bed residential home with porch

BeatriceRating, 5 stars9 months ago

Elena's place was really lovely and her uncle and aunt, who checked us in, were very welcoming and understanding when we arrived later than we had initially said but couldn't inform them because data wasn't working on our phones. They also took us in the car to show us the nearest supermarket and restaurants and gave us tips on the area. The wifi didn't work on the first evening as there was a problem island wide and the engineer hadn't shown up that day, but it was quickly resolved the following day. Communication was very smooth throughout the entire process. Our neighbours, a lovely couple who are long term tenants in the flat below the one we stayed in, were extremely friendly and helpful - one day they even brought us some guineps (Spanish limes) which were delicious. St John's, like all of Montserrat, was full of very lovely and welcoming people. And it's a great location from where you can easily get to any part of the island.

A glass of water with a lemon slice rests on a tiled surface beside a swimming pool. The clear blue of the pool water reflects light, creating a pattern on the surrounding area, contributing to a relaxed atmosphere.

Bungalow in Woodlands

Runaway Hideaway, your Caribbean cottage

PaulRating, 5 stars28 months ago

Runaway Hideaway is spacious, tastefully decorated, and set within a lush, sheltered and well kept garden. It had everything we needed for a self contained vacation, and we felt at home from the first minute to the last. It was peaceful and we dropped off to sleep every night to the sound of the tree frogs, and woke to the sound of the cockerels. The photographs if anything don’t do it justice, and you get a sunset view every evening. Ryan and Henry could not have been any more helpful, to the extent that when our travel was disrupted they were able to help us with suggestions and tips that were truly welcome at a stressful time. The local property managers were on hand for anything, and everyone simply wanted to make sure we had a great holiday. We did. We love Montserrat. We loved Runaway Hideaway.