
Holiday rentals in Old Town
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Top-rated holiday rentals in Old Town
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Other great holiday rentals in Old Town
Guest favourite

Home in Jolly Harbour
5 out of 5 average rating, 7 reviewsSpectacular Caribbean-Sunset-Ocean-view home!
RebeccaRating, 5 stars2 months ago
Wonderful villa, beautiful views, gorgeous pool, lots of space, nicely furnished, beautifully clean, very well kitted out. Had a few issues at beginning but hosts v responsive and keen to sort quickly. Would have been great to have an information booklet / folder with practical info about the villa but also recommendations / opinions about restaurants, beaches, excursions etc. The hosts were very helpful - but just useful to have this kind of thing in any accommodation you stay in. It was a shame about the construction noise - beyond their control I know. Mainly it was in the distance but sometimes it was enough to send us to the beach rather than relaxing at the villa. In the main though a wonderful villa which we all enjoyed being in and particularly the beautiful views during the day and at sunset 🌅 - thank you Patrick and the team for all your help.

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.

Apartment in Woodlands
4.8 out of 5 average rating, 10 reviewsMin-y-Don, Montserrat Caribbean hideaway
CatherineRating, 5 stars4 months ago
Our stay at Min Y Don was wonderful. The house is in an incredibly beautiful and convenient spot. Hearing the waves crashing below, the warm breeze in the palms, birds in the day and a chorus of tree frogs at night was bliss. The view over the ocean is amazing. The accommodation is so comfortable and spacious, everything you could possibly need for a luxurious stay. Well equipped kitchen, wonderful pool (with pool toys!) and such comfy beds. Sian and Peter have been so kind, generous, and friendly throughout. They've thought of everything, suncream abd shampoo, baked bread on arrival, and chilled water in the fridge. Lots of information on Montserrat too. To say we enjoyed our stay is an understatement. I was working part of the time, exploring the rest; and having such a beautiful and welcoming home to return to was the icing on the cake. Thankyou Sian and Peter.
Guest favourite

Flat in Urlings
4.83 out of 5 average rating, 6 reviewsDream View Apartment
RalitsaRating, 5 stars5 months ago
This place is a hidden gem. Darryl and Daff are extremely kind and interesting hosts. Their stories about the island, the people and the culture are very insightful and make the exploration of the island much more interesting. The location is the best possible one on the island : we had access to all the best beaches , just in close distance. Watching the blue water and the sunset from the balcony was our favorite part. We were having coffee in the morning while watching the humming birds flying around the blooming flowers in front of the balcony. The house has everything that we needed and even more: the beach beds, the snorkeling gears.. they have thought of every detail to make our stay easy and enjoyable. It was one of the best places that we have stayed so far. Thank you, guys. We will be back.

Cottage in Valley Church
5 out of 5 average rating, 4 reviewsCaribbean Sea View Cottage
TriciaRating, 5 stars1 week ago
Oana and Flo were fantastic hosts. Super fast responding to my questions before and after I booked with very clear communication. Great to have them living nearby so they were always on hand with helpful advice, some local fish steaks, or just to stop for a chat and help with anything else we needed. Lovely local fruit and wine in the fridge to welcome us. The cottage was lovely - newly refurbished, fantastic views looking out over the private garden to the ocean and close to local amenities at Jolly Harbour, beaches etc. Also had good shutters on all the windows and fly screens so we could have a breeze flowing through without the insects! Quiet and peaceful. Car rental from Flo was great. Much less hassle and better price than a car hire company. Their parking space is covered so the car doesn’t bake in the sun. We stayed a week and liked Darkwood beach, and other recommendations from Oana. Would also recommend jollysnorkellingtours for a personalized trip.
Guest favourite

Villa in Saint Peter's
4.9 out of 5 average rating, 10 reviewsVilla Isotica: Scenic and Breathtaking Views
KarenRating, 5 stars2 months ago
Montserrat is a beautiful and quiet island but there isn’t a whole lot in terms of infrastructure or options — so it’s worth knowing what to expect. This Airbnb was incredibly expensive for what it is, but given the context, that’s not entirely surprising. Choices on the island are limited and basic so this was luxurious comparatively. The space was clean, thoughtfully decorated, and clearly well taken care of. It doesn’t have AC but based on location in the hills it has an awesome breeze and sleeping at night was comfortable. Beautiful orchestra of tree frogs! Daphne and Norman were extremely friendly and helpful - clearly care for their guests and want them to have a good time. They helped organize a car from Jerret (tip top enterprise) and we highly recommend him. He met us at the airport and was super easy to deal with. The car was brilliant - without it you would be unable to move around. The roads are difficult to navigate so important to important to have a good.
Top guest favourite

Flat in Davy Hill
5 out of 5 average rating, 25 reviewsRELAX-IN: 2-bedroom apartment w/ Jeep rental svcs
RyanRating, 5 stars3 days ago
Lyandra was incredibly helpful before and during our trip. She was very knowledgeable with local recommendations, and had a great "cliff notes" guidebook available. check-in and checkout was smooth, and she was accommodating to keeping our bags secure since our flight left hours after checkout! Very easy to work with and cute home.
Guest favourite

Guest house in Saint Mary
4.86 out of 5 average rating, 22 reviewsJay's home away from home w/ private Swimming Pool
OniquaRating, 5 stars2 weeks ago
Julian was a great host. Very responsive and always checking in to make sure I was comfortable or needed anything. I enjoyed my stay.
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