Villa in Leeward Islands
10 guests · 5 bedrooms · 5 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
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About this villa rental
Montserrat Breezes is a beautifully appointed five bedroom, five and a half bath private Villa located high in the Woodlands section of Montserrat. Lovingly and carefully constructed by one of America's wealthiest families and updated by it's present owners, Montserrat Breezes boasts over 6000 square feet of indoor and outdoor living spaces, with breathtaking views (especially at Sunset) of the Caribbean Sea from virtually all living areas. Three king suites (all with king beds) feature spacious rooms with Plantation Shutters, en-suite baths and private verandas. Two lower suites include one king bedroom and an adjoining twin bedroom. Both of these bedrooms offer open ocean views, en-suite baths, and a shared covered veranda. The door between these bedrooms can be locked for privacy or opened for families with children.
This villa was designed to maximize the ocean views from all rooms with large 'disappearing' glass and screen panels in each room. In addition, the open air dining and family rooms feature large Plantation Shutters on the rear wall, which open to view the private courtyard and manicured garden. The grounds are tiered with stone walls and are extensively landscaped with multiple varieties of palms, flowering trees and bushes. The lower grounds have bananas, lemons,guava,coconuts and grapefruit (when in season).
Children will enjoy the variety of lizards, toads, and birds found on and around the property. Bring flashlights--the toads come out at night.
Montserrat Breezes will easily accommodate an extended family, two small families or up to five couples. The lower full kitchen is perfect for poolside dining or entertaining.
This villa is cooled by nearly constant trade winds and is situated across from an entrance to the famous Mountain Trails of Montserrat. It is ideal for hikers and nature enthusiasts.
***This villa is not suitable for toddlers or youths who cannot swim or would be inclined to push on the floor to ceiling screen panels. Renters assume full responsibility for pool safety.
Keywords: Villa
This villa was designed to maximize the ocean views from all rooms with large 'disappearing' glass and screen panels in each room. In addition, the open air dining and family rooms feature large Plantation Shutters on the rear wall, which open to view the private courtyard and manicured garden. The grounds are tiered with stone walls and are extensively landscaped with multiple varieties of palms, flowering trees and bushes. The lower grounds have bananas, lemons,guava,coconuts and grapefruit (when in season).
Children will enjoy the variety of lizards, toads, and birds found on and around the property. Bring flashlights--the toads come out at night.
Montserrat Breezes will easily accommodate an extended family, two small families or up to five couples. The lower full kitchen is perfect for poolside dining or entertaining.
This villa is cooled by nearly constant trade winds and is situated across from an entrance to the famous Mountain Trails of Montserrat. It is ideal for hikers and nature enthusiasts.
***This villa is not suitable for toddlers or youths who cannot swim or would be inclined to push on the floor to ceiling screen panels. Renters assume full responsibility for pool safety.
Keywords: Villa
Amenities
Non-smoking
No pets allowed
Map of Leeward Islands
Ratings and reviews
10 / 10Outstanding·Jun 2026
Our stay at this villa was fantastic. From the moment we booked until checkout, communication with the host was outstanding—responsive, helpful, and professional throughout.The views from the property are simply breathtaking and were one of the highlights of our trip. The grounds are beautiful and well maintained, creating a serene setting that perfectly complements the villa’s quiet and private location.The home was very clean, and the beds were incredibly comfortable, ensuring a restful stay. We also appreciated how well equipped the kitchen and house were, making it easy to prepare meals and enjoy time together. A major plus for our group was that each guest had their own bedroom and bathroom, which provided plenty of comfort and privacy.Although the property shows some signs of age, it remains full of charm and character. The beauty of the setting, the comfort of the accommodations, and the thoughtful amenities far outweighed any minor signs of wear.We thoroughly enjoyed our stay and would not hesitate to return. Highly recommended for anyone looking for a peaceful getaway with stunning views in Montserrat.
10 / 10Outstanding·Jan 2026
After a long 3-4 flight travel from CA and CO, Pickett met us at airport as well as secured a second car for our group of 8. They transported us to the beautiful Montserrat Breezes where we had 2 rental vehicles for our 8 days.We had cruised past Montserrat in the early 90’s and it was so beautiful and the Ship Captain very complimentary. Our son remembered this and suggested we visit this island for our Christmas 2025 trip. 3 generations which included 2 grandsons, ages 10 and 8. This villa was perfect for our stay and is just lovely. It is located in a very private and relaxing locale. It was very nice with all bedrooms having their own baths and a laundry room to use. Our favorite beach was a short drive and 4 of our party secured the Montserrat driver’s license that was required. Weather was perfect with a couple brief rain showers and when a “cut off” on power occurred, they were brief. We dined at Isle Bar and Grill, Scoreboard, birthday dinner at Ovelston House, festive Xmas Eve dinner at Watermelon Cottage, Xmas Day Take Away dinner by Jessica, private beach dinner at Old Road Beach, boat tour by Andy to view the destruction of the restricted part of the island due to the volcano, a welcoming Christmas Mass at St. Martin’s and 4 enjoyed a shore scuba tour. As a homage to the villa’s heritage, a big bag of Mars candy was brought to enjoy! Mike, the host was always available via a text with answers and suggestions to any of our concerns. I say, Just Book It
10 / 10Outstanding·Dec 2025
Montserrat is a magical place where time slows down. This villa is gorgeous, exactly as pictured here. We had the trip of a lifetime.
5 / 10·Apr 2019
A beautiful property with spacious well planned rooms with en-suites and beautiful well maintained pool with the individual in mind.The property is exceptional, well maintained by Anita and Pickett who I commend for their excellent customer service and care and attention to detail.I would also like to say a big thank to Mike the owner of Breezes for his excellent customer service and prompt responses to my emails.A big thank you to you all.Judie Marsh
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Top rated by guests
10Outstanding
(47 Ratings)
"Our stay at this villa was fantastic. From the moment we booked until checkout, communication with the host was outstanding—responsive, helpful, and professional throughout.The views from the property..."
Margaret A. L.Don't miss out! Price and availability may change
