
Vacation rentals with a pool in Montserrat
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Top-rated rentals with a pool in Montserrat
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Popular amenities for Montserrat rentals with a pool
House rentals with a pool

Home in Woodlands
4.82 out of 5 average rating, 22 reviewsCrows Nest Villa...2 bed with pool
RussRating, 5 stars10 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.

Home in Old Town
Bananaquit at the beach!
ClysiaRating, 5 stars15 months ago
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.

Home in Old Town
4.4 out of 5 average rating, 5 reviewsOld Town Studio w/Separate Affiliated Pool House
SeanRating, 5 stars2 months ago
I really couldn't have asked for a better all-around place to stay in Montserrat! It's a basic but comfortable accommodation, with 2 beds, a well-stocked kitchen, fridge, a shower with hot water, and lots of strong fans - but no air conditioning. The wifi worked perfectly throughout my stay, and at a consistent 100 Mbps download speed it might even be the fastest in all of Montserrat, which made getting some remote work done here a breeze. Very easy checkin - the hosts helped me arrange a taxi in advance to bring me to the place from the airport, which I'd highly recommend as there aren't many taxis waiting at arrivals. It's also in a great location, very quiet and peaceful, around a 15 minute walk downhill to the famous black sand Lime Kiln Beach, and a 20 minute walk uphill to the nearest restaurants in Salem. Jerely and Mikhaila are also outstanding hosts - they are extremely responsive and friendly and made checking in and out super easy.

Home in Saint Peter's
Silk Cotton Villa
SarahRating, 5 stars5 months ago
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!

Home in Old Town
Chez Mango Luxury Oceanview Villa

Home in Old Town
See Forever Villa

Home in woodlands
Villa Traquilla
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