
House holiday rentals in Montserrat
Find and book unique houses on Airbnb
Top-rated house rentals in Montserrat
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Montserrat house rentals
House rentals with a pool

Crows Nest Villa...2 bed with pool
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.

NEW Stylish Caribbean 3 Bdrm Villa
If there was any surprise, it was really how lovely the house and the setting was... pictures don't do it justice! All the conveniences of home and more in a lush tropical setting...we couldn't ask for more! Todd was super responsive as a host and provided many suggestions that made our stay even more enjoyable. Same for Mark, the property manager! Will definitely stay here again when we come back!

Amazing Villa Tropicasa
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!)

Bananaquit at the beach!
This was my 5th trip to Montserrat. Each time I’ve stayed I’ve rented an AirBnB or stayed with friends. This home, by far, was my most enjoyable and comfortable stay! Upon entry it was clean and spacious. Amenities and household items were plentiful and well thought out. The views are spectacular. I will continue to book this home whenever I can. The only minor drawback was that the listed description for the 2nd bedroom did not match what was actually there - only 1 bed instead of 2. But the 2nd bed was in the private apartment downstairs.

Enchanting private retreat
This place was amazing! The views incredible! The grounds were like a botanical garden. The bedroom, bath, sitting area and full kitchen was great amount of space for my husband and I. Actually, the sitting area outside, we used the most. My husband purchased a fan because the heat and humidity got to him at night, well I needed it too. A rooster woke us up every morning around 5am. You don't need an alarm clock on the island. lol. The chickens roam free. There are so many species of birds and other wildlife on the island to admire. The electricity went off for a few hours, Kristy Lee the house manager, showed up with repairman and then called the electric company which had it back on within the hour. She responded promptly and was so nice. It's not unexpected for the electricity to go off at times for a short while, so we waited a while before we called. Kristy said to feel free to call as soon as it goes out. The internet is very fast. You could stream movies with it. Lovely time!

Silk Cotton Villa
Silk Cotton Villa was an absolutely lovely place to stay during our first trip to Montserrat. The house is well equipped with fans, air conditioning, and WiFi. The pool is gorgeous, and the views are unbelievable. The beds are excellent quality. The location is literally minutes away from lovely hiking trails. We are extremely grateful to Alvonne for his help navigating some airport difficulties. He also helped us with so many other aspects of our trip. He connected us with tour guides and a taxi driver. He also shared many personal recommendations, including island information and history with us. Our trip was unforgettable, and we would return to Silk Cotton Villa in a heartbeat!

Family Beachside Living with Oceanviews & Pool
Great location on island, essentially within 20 minutes’ drive of all places of interest/accessible points, yet serenely secluded and quiet (except for lapping surf!). 5 minute walk to the beautiful Woodlands Beach for bathing and snorkelling, often having site to one’s self. First class communication throughout with both owner and local agent, plus the most comprehensive local user guide we have ever received at an AirBnB. Light and airy open-plan living area with ocean views, leading to two separate outdoor dining areas on opposing aspects, one sheltered and one covered. Kitchen equipped with all utensils and appliances required for cooking elaborate meals. Local supermarkets only 10 min drive in either direction plus local food stalls for fresh produce. Although not air conditioned, this was never an issue with great ventilation/local climate and ceiling fans are provided too. Tastefully furnished with more than ample seating options. Large well-maintained swimming pool.

Oasis Villa
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.
Weekly house rentals

Crows Nest Villa...2 bed with pool
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.

NEW Stylish Caribbean 3 Bdrm Villa
If there was any surprise, it was really how lovely the house and the setting was... pictures don't do it justice! All the conveniences of home and more in a lush tropical setting...we couldn't ask for more! Todd was super responsive as a host and provided many suggestions that made our stay even more enjoyable. Same for Mark, the property manager! Will definitely stay here again when we come back!

Amazing Villa Tropicasa
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!)

Bananaquit at the beach!
This was my 5th trip to Montserrat. Each time I’ve stayed I’ve rented an AirBnB or stayed with friends. This home, by far, was my most enjoyable and comfortable stay! Upon entry it was clean and spacious. Amenities and household items were plentiful and well thought out. The views are spectacular. I will continue to book this home whenever I can. The only minor drawback was that the listed description for the 2nd bedroom did not match what was actually there - only 1 bed instead of 2. But the 2nd bed was in the private apartment downstairs.

Enchanting private retreat
This place was amazing! The views incredible! The grounds were like a botanical garden. The bedroom, bath, sitting area and full kitchen was great amount of space for my husband and I. Actually, the sitting area outside, we used the most. My husband purchased a fan because the heat and humidity got to him at night, well I needed it too. A rooster woke us up every morning around 5am. You don't need an alarm clock on the island. lol. The chickens roam free. There are so many species of birds and other wildlife on the island to admire. The electricity went off for a few hours, Kristy Lee the house manager, showed up with repairman and then called the electric company which had it back on within the hour. She responded promptly and was so nice. It's not unexpected for the electricity to go off at times for a short while, so we waited a while before we called. Kristy said to feel free to call as soon as it goes out. The internet is very fast. You could stream movies with it. Lovely time!

Family Beachside Living with Oceanviews & Pool
Great location on island, essentially within 20 minutes’ drive of all places of interest/accessible points, yet serenely secluded and quiet (except for lapping surf!). 5 minute walk to the beautiful Woodlands Beach for bathing and snorkelling, often having site to one’s self. First class communication throughout with both owner and local agent, plus the most comprehensive local user guide we have ever received at an AirBnB. Light and airy open-plan living area with ocean views, leading to two separate outdoor dining areas on opposing aspects, one sheltered and one covered. Kitchen equipped with all utensils and appliances required for cooking elaborate meals. Local supermarkets only 10 min drive in either direction plus local food stalls for fresh produce. Although not air conditioned, this was never an issue with great ventilation/local climate and ceiling fans are provided too. Tastefully furnished with more than ample seating options. Large well-maintained swimming pool.

Oasis Villa
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.

Providence: Paul McCartney's former hideaway
Thank you for a wonderful stay! Montserrat is a special place and the house where we stayed was lovely. Thank you for being so responsive and kind. We will be back again!
Private house rentals

Crows Nest Villa...2 bed with pool
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.

NEW Stylish Caribbean 3 Bdrm Villa
If there was any surprise, it was really how lovely the house and the setting was... pictures don't do it justice! All the conveniences of home and more in a lush tropical setting...we couldn't ask for more! Todd was super responsive as a host and provided many suggestions that made our stay even more enjoyable. Same for Mark, the property manager! Will definitely stay here again when we come back!

Amazing Villa Tropicasa
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!)

Bananaquit at the beach!
This was my 5th trip to Montserrat. Each time I’ve stayed I’ve rented an AirBnB or stayed with friends. This home, by far, was my most enjoyable and comfortable stay! Upon entry it was clean and spacious. Amenities and household items were plentiful and well thought out. The views are spectacular. I will continue to book this home whenever I can. The only minor drawback was that the listed description for the 2nd bedroom did not match what was actually there - only 1 bed instead of 2. But the 2nd bed was in the private apartment downstairs.

Enchanting private retreat
This place was amazing! The views incredible! The grounds were like a botanical garden. The bedroom, bath, sitting area and full kitchen was great amount of space for my husband and I. Actually, the sitting area outside, we used the most. My husband purchased a fan because the heat and humidity got to him at night, well I needed it too. A rooster woke us up every morning around 5am. You don't need an alarm clock on the island. lol. The chickens roam free. There are so many species of birds and other wildlife on the island to admire. The electricity went off for a few hours, Kristy Lee the house manager, showed up with repairman and then called the electric company which had it back on within the hour. She responded promptly and was so nice. It's not unexpected for the electricity to go off at times for a short while, so we waited a while before we called. Kristy said to feel free to call as soon as it goes out. The internet is very fast. You could stream movies with it. Lovely time!

Family Beachside Living with Oceanviews & Pool
Great location on island, essentially within 20 minutes’ drive of all places of interest/accessible points, yet serenely secluded and quiet (except for lapping surf!). 5 minute walk to the beautiful Woodlands Beach for bathing and snorkelling, often having site to one’s self. First class communication throughout with both owner and local agent, plus the most comprehensive local user guide we have ever received at an AirBnB. Light and airy open-plan living area with ocean views, leading to two separate outdoor dining areas on opposing aspects, one sheltered and one covered. Kitchen equipped with all utensils and appliances required for cooking elaborate meals. Local supermarkets only 10 min drive in either direction plus local food stalls for fresh produce. Although not air conditioned, this was never an issue with great ventilation/local climate and ceiling fans are provided too. Tastefully furnished with more than ample seating options. Large well-maintained swimming pool.

Oasis Villa
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.

Providence: Paul McCartney's former hideaway
Thank you for a wonderful stay! Montserrat is a special place and the house where we stayed was lovely. Thank you for being so responsive and kind. We will be back again!
Destinations to explore
- Family-friendly rentals Montserrat
- Rentals with beach access Montserrat
- Pet-friendly rentals Montserrat
- Apartment rentals Montserrat
- Rentals with outdoor seating Montserrat
- Rentals with a washing machine and dryer Montserrat
- Villa rentals Montserrat
- Rentals with a patio Montserrat
- Rentals with pools Montserrat
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom