House vacation rentals in Montserrat

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Popular amenities for Montserrat house rentals

House rentals with a pool

The image captures a sunlit pool area with a sparkling pool surrounded by patio tiles. White lounge chairs with blue and white stripes are arranged nearby. Lush greenery is visible at the pool's edge, with the expansive Caribbean Sea in the background under a bright sky.
Home in Woodlands
4.82 out of 5 average rating, 22 reviews

Crows Nest Villa...2 bed with pool

RussRating, 5 stars8 months ago
Unfortunately, I can’t honestly review Tom & Chrystal’s place. Tom had reached out a couple of weeks prior to inform me that due to scheduling issue, he had made arrangements for us stay at another villa, which was absolutely amazing! By chance we ran into Tom and family at the local dive shop, and we ended up eating lunch together. Everything I had come to learn online was met in person: kind, friendly, funny, generous… Good people, and we count ourselves lucky to have gotten to spend time with them. So, even though I can’t speak about Crow’s Nest in Woodlands, I can say my interactions with Tom and Chrystal were 100% positive, and I would happily stay at their place at the next opportunity.
A curvilinear swimming pool is framed by tiled decking, featuring lounge chairs in vibrant colors. An adjacent hot tub is nestled into the pool area. Lush greenery surrounds the space, contributing to a serene outdoor environment.
Home in Salem
4.57 out of 5 average rating, 23 reviews

Amazing Villa Tropicasa

VictoriaRating, 5 stars22 months ago
We had a lovely stay at Kenneth’s! We were visiting on a work trip and the location was great for us, including being a peaceful base for getting some work done. Ken helped us arrange a local car rental and was very quick to support us when we struggled to unlock the garage door (our error!). Ken and his fab team left us with great info on local things to do and we were in easy walking distance to two great restaurants (Olveston House and Vue Point) as well as Lime Kiln Beach. We hope to be back again soon (we drank from the burn at Runaway Ghaut to be sure of it!)
A serene exterior view of the Caribbean villa is presented, featuring a driveway leading to the entrance. A sleek vehicle is parked beside the house, which is surrounded by lush greenery. The inviting swimming pool is visible to the right, nestled in the garden.
Home in Woodlands
5 out of 5 average rating, 3 reviews

Oasis Villa

NatalieRating, 5 stars24 months ago
We had a lovely stay. Everton and the property manager, Dwayne, were really helpful and responsive via email. We were given the property address and various helpful instructions well in advance of our stay, which made finding the property easy when we arrived. The villa itself is beautiful. There’s so much indoor space and a lovely terrace off the kitchen. The pool was lovely, a great temperature and very clean. Wilson popped around twice during our two-week stay to keep it clean and maintain the terrace tiles too. The kitchen was well-equipped and there was everything you needed to cook with. There were cleaning materials too. The bathroom even had a hair dryer which was unexpected! All furniture was very practical and comfortable, the mattresses were very comfortable and bedding provided was great. There were even pool towels! The location was perfect, a couple of minutes’ drive from Woodlands Beach and Salem and within easy reach of the rest of the island.
Top guest favorite
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, 16 reviews

Providence: Paul McCartney's former hideaway

HassanRating, 5 stars1 month ago
The property is nicely equipped with all the amenities and comforts of home and outdoor living. The sunsets are spectacular, the surroundings lush and the sea pristine. For calm, rejuvenation and getting in touch with oneself, this is the perfect place. Repeat future visits are a certainty.
A bright pool area is surrounded by lush tropical landscaping, showcasing a stunning blue water pool. The villa features a round design with white railings and a covered porch, providing ample space for relaxation under the clear sky and gentle clouds.
Home in Garibaldi Hill
5 out of 5 average rating, 4 reviews

Beautiful Caribbean Villa with spectacular views

CatherineRating, 5 stars9 months ago
The pool, the pool, the pool. Oh, and yes the house and the views. We had a wonderful stay at Trelawney. The pictures were very accurate, although the magnificence of the views can only be captured in person. We were in Montserrat for a family reunion which had many planned activities. However when we had any down time, we were in the pool. The pool was immaculate, and Robbyn did a wonderful job of keeping it that way. Asha was wonderful as well, very thorough and very personable. Adrienne was very helpful in letting us know where to shop for food as well as suggesting what we could bring with us. She also helped us secure transportation. Winston was wonderful and we used him for the entire time that we were on the island. It was so wonderful to be back on the island, our first time since the volcano. Adrienne was very responsive any time that we reached out to her. Thank you for sharing your beautiful home. We would gladly stay there again.

Weekly house rentals

The image captures a sunlit pool area with a sparkling pool surrounded by patio tiles. White lounge chairs with blue and white stripes are arranged nearby. Lush greenery is visible at the pool's edge, with the expansive Caribbean Sea in the background under a bright sky.
Home in Woodlands
4.82 out of 5 average rating, 22 reviews

Crows Nest Villa...2 bed with pool

RussRating, 5 stars8 months ago
Unfortunately, I can’t honestly review Tom & Chrystal’s place. Tom had reached out a couple of weeks prior to inform me that due to scheduling issue, he had made arrangements for us stay at another villa, which was absolutely amazing! By chance we ran into Tom and family at the local dive shop, and we ended up eating lunch together. Everything I had come to learn online was met in person: kind, friendly, funny, generous… Good people, and we count ourselves lucky to have gotten to spend time with them. So, even though I can’t speak about Crow’s Nest in Woodlands, I can say my interactions with Tom and Chrystal were 100% positive, and I would happily stay at their place at the next opportunity.
A serene pool area is featured, showcasing a main swimming pool surrounded by a spacious deck. Colorful lounge chairs are positioned nearby, and a whirlpool is integrated with natural stone accents. Lush greenery and clear skies provide an inviting backdrop for relaxation.
Home in Salem
4.57 out of 5 average rating, 23 reviews

Amazing Villa Tropicasa

VictoriaRating, 5 stars22 months ago
We had a lovely stay at Kenneth’s! We were visiting on a work trip and the location was great for us, including being a peaceful base for getting some work done. Ken helped us arrange a local car rental and was very quick to support us when we struggled to unlock the garage door (our error!). Ken and his fab team left us with great info on local things to do and we were in easy walking distance to two great restaurants (Olveston House and Vue Point) as well as Lime Kiln Beach. We hope to be back again soon (we drank from the burn at Runaway Ghaut to be sure of it!)
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, 3 reviews

Oasis Villa

NatalieRating, 5 stars24 months ago
We had a lovely stay. Everton and the property manager, Dwayne, were really helpful and responsive via email. We were given the property address and various helpful instructions well in advance of our stay, which made finding the property easy when we arrived. The villa itself is beautiful. There’s so much indoor space and a lovely terrace off the kitchen. The pool was lovely, a great temperature and very clean. Wilson popped around twice during our two-week stay to keep it clean and maintain the terrace tiles too. The kitchen was well-equipped and there was everything you needed to cook with. There were cleaning materials too. The bathroom even had a hair dryer which was unexpected! All furniture was very practical and comfortable, the mattresses were very comfortable and bedding provided was great. There were even pool towels! The location was perfect, a couple of minutes’ drive from Woodlands Beach and Salem and within easy reach of the rest of the island.
Top guest favorite
A narrow, paved pathway meanders through lush greenery, leading towards a white house with pink accents in the distance. Towering palm trees and tropical plants frame the walkway, creating a natural corridor that enhances the tranquil setting.
Home in St Peter's Village
5 out of 5 average rating, 16 reviews

Providence: Paul McCartney's former hideaway

HassanRating, 5 stars1 month ago
The property is nicely equipped with all the amenities and comforts of home and outdoor living. The sunsets are spectacular, the surroundings lush and the sea pristine. For calm, rejuvenation and getting in touch with oneself, this is the perfect place. Repeat future visits are a certainty.

Private house rentals

The image captures a sunlit pool area with a sparkling pool surrounded by patio tiles. White lounge chairs with blue and white stripes are arranged nearby. Lush greenery is visible at the pool's edge, with the expansive Caribbean Sea in the background under a bright sky.
Home in Woodlands
4.82 out of 5 average rating, 22 reviews

Crows Nest Villa...2 bed with pool

RussRating, 5 stars8 months ago
Unfortunately, I can’t honestly review Tom & Chrystal’s place. Tom had reached out a couple of weeks prior to inform me that due to scheduling issue, he had made arrangements for us stay at another villa, which was absolutely amazing! By chance we ran into Tom and family at the local dive shop, and we ended up eating lunch together. Everything I had come to learn online was met in person: kind, friendly, funny, generous… Good people, and we count ourselves lucky to have gotten to spend time with them. So, even though I can’t speak about Crow’s Nest in Woodlands, I can say my interactions with Tom and Chrystal were 100% positive, and I would happily stay at their place at the next opportunity.
A serene pool area is featured, showcasing a main swimming pool surrounded by a spacious deck. Colorful lounge chairs are positioned nearby, and a whirlpool is integrated with natural stone accents. Lush greenery and clear skies provide an inviting backdrop for relaxation.
Home in Salem
4.57 out of 5 average rating, 23 reviews

Amazing Villa Tropicasa

VictoriaRating, 5 stars22 months ago
We had a lovely stay at Kenneth’s! We were visiting on a work trip and the location was great for us, including being a peaceful base for getting some work done. Ken helped us arrange a local car rental and was very quick to support us when we struggled to unlock the garage door (our error!). Ken and his fab team left us with great info on local things to do and we were in easy walking distance to two great restaurants (Olveston House and Vue Point) as well as Lime Kiln Beach. We hope to be back again soon (we drank from the burn at Runaway Ghaut to be sure of it!)
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, 3 reviews

Oasis Villa

NatalieRating, 5 stars24 months ago
We had a lovely stay. Everton and the property manager, Dwayne, were really helpful and responsive via email. We were given the property address and various helpful instructions well in advance of our stay, which made finding the property easy when we arrived. The villa itself is beautiful. There’s so much indoor space and a lovely terrace off the kitchen. The pool was lovely, a great temperature and very clean. Wilson popped around twice during our two-week stay to keep it clean and maintain the terrace tiles too. The kitchen was well-equipped and there was everything you needed to cook with. There were cleaning materials too. The bathroom even had a hair dryer which was unexpected! All furniture was very practical and comfortable, the mattresses were very comfortable and bedding provided was great. There were even pool towels! The location was perfect, a couple of minutes’ drive from Woodlands Beach and Salem and within easy reach of the rest of the island.
Top guest favorite
A narrow, paved pathway meanders through lush greenery, leading towards a white house with pink accents in the distance. Towering palm trees and tropical plants frame the walkway, creating a natural corridor that enhances the tranquil setting.
Home in St Peter's Village
5 out of 5 average rating, 16 reviews

Providence: Paul McCartney's former hideaway

HassanRating, 5 stars1 month ago
The property is nicely equipped with all the amenities and comforts of home and outdoor living. The sunsets are spectacular, the surroundings lush and the sea pristine. For calm, rejuvenation and getting in touch with oneself, this is the perfect place. Repeat future visits are a certainty.

Destinations to explore