First I would like to say that the owner was kind and nice. Most of our interaction was with the property manager, Jason. He is a five star property manager. Excellent communication, very helpful. Available immediately upon need. Amazing! First impression of this house are incredible. The view is spectacular and it has luxurious features like 2 kitchens, a spacious pool, 5 BRs and more. It presents as an upscale location. It is also priced that way. BUT BEWARE: If you want to stay here, you should know there are quite a number of serious issues with the house that turn it into a low-scale experience. First of all, understand that though it says the BRs have AC, none of the rooms are fully sealed. All rooms have hurricane screens. No matter how high you turn up the AC, all rooms will be relatively hot, humid, and damp. Secondly, though it's on a hill and advertised to have great breezes off the sea, remember that this is an island and it's hot. During the day in the summer, the living areas will be about 85 degrees F and barely get into the 70s F at night. And again, everything will be damp because of the sea breeze and frequent showers. With the open window concept, perhaps the greatest problem is with bugs. There is almost no stopping a large infestation of ants. We tried to clean up every night and wash dishes & sweep the floor. It didn't matter. We had a box of cereal that had been opened, but closed back up with the plastic rolled down. Hundreds of ants came in over night and crawled up the box and into the cereal. There was a bottle of sweet wine that we had on the counter. Within an hour the entire bottle was covered with ants. So managing food is nearly impossible. And of course with ants, you'll have tons of spiders. You should also know that this is in a heavily forested area which means TONS of mosquitos. There are so many that the outdoors spaces couldn't even be used at night. Finally, there are other design flaws such as: a poorly placed window so people on the street can see you shower or in the bathroom clearly at night and unsealed door jambs so mosquitos will fly in and bite you while you sleep. My children were covered in bites and welts, poor drainage on the pool so if you splash, it goes onto the downstairs patio and will stream into BRs. Lastly, you should not say here if you don't have a vehicle that can handle extremely steep drives. 5 star+ hosting, 2 star experience

We had an amazing time at the Leeward House. Better than the pictures & very comfortable. Jason was so accommodating & always available. Couldn’t say enough positive things about our stay. Layout of the house & the view was perfect too!

We had an amazing time at the Leeward House. Better than the pictures & very comfortable. Jason was so accommodating & always available. Couldn’t say enough positive things about our stay. Layout of the house & the view was perfect too!

Incredible experience made even more special by Jason and his hosting! The property is stunning, secluded up a mountainside where we didn’t see anyone for the whole time we were there. Stunning views of the ocean and Montserrat… with every night ending with the most spectacular sunset! The property is exactly as described. But even more than this was Jason’s generous hosting. From the provisions run on arrival to the check ins throughout our stay, our experience was made even better by him and his warm hosting.

Incredible experience made even more special by Jason and his hosting! The property is stunning, secluded up a mountainside where we didn’t see anyone for the whole time we were there. Stunning views of the ocean and Montserrat… with every night ending with the most spectacular sunset! The property is exactly as described. But even more than this was Jason’s generous hosting. From the provisions run on arrival to the check ins throughout our stay, our experience was made even better by him and his warm hosting.