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Holiday houses in Lookout

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Popular amenities for Lookout holiday rentals

Other great holiday rentals in Lookout

Guest favourite
Home in Jolly Harbour
5 out of 5 average rating, 7 reviews

Spectacular 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 reviews

Crows 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 Salem
4.57 out of 5 average rating, 23 reviews

Amazing Villa Tropicasa

VictoriaRating, 5 stars24 months ago
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!)
Top Guest favourite
Cottage in Sawcolts
5 out of 5 average rating, 5 reviews

Peaceful nature escape

AndreasRating, 5 stars3 months ago
We had a wonderful time in Andrews Sugar Cottage. It is very nice cottage in a calm setting surrounded by a green garden and jungle sounds. We didnt meet him or his assistant in person but the communication and service was flawless - we were even greeted with a fruit basket and a starter pack, thanks! We enjoyed the big terrace a lot and are already looking back to evenings just waiting for the sun to go down and listening to the island sounds. There is also the lovely house dog Mango - very friendly and attentive. There are also other dogs in this area so there is some barking going on during the day. Be aware of the mosquitos and get used to carry the provided mosquito bats along. You will also need a car to get to all the beaches, restaurants and sights. We highly recommend the cottage for people who want to stay away from the big resorts and feel more like a local. We loved it and would definitely book again. Thanks Andrew and Mowava for this unique stay!
Condo in Woodlands
4.8 out of 5 average rating, 10 reviews

Min-y-Don, Montserrat Caribbean hideaway

CatherineRating, 5 stars3 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.
Villa in Saint Peter Parish
5 out of 5 average rating, 5 reviews

Breathtaking Villa Vera w/ Infinity pool & views

GillianRating, 5 stars26 months ago
The villa was lovely with beautifully kept gardens all around it. A nice veranda too with lovely garden furniture which was nice to sit in the shade. Location was perfect for us, although need a car. Pool was great & very clean. Initially had an issue with it which was immediately dealt with & Wendell was always on hand should we have needed him. Only negatives: No air con in the lounge area or bed 3. No trays to use in the oven for cooking, which is a minor point. Overall really pleased with this pretty villa & wouldn’t hesitate recommending it to others. Thank you Wendell for a lovely holiday
Villa in Old Town
5 out of 5 average rating, 8 reviews

Oceanfront Luxurious Villa Stunning Sunsets Avalon

JeffRating, 5 stars7 months ago
Montserrat is a beautiful island with a unique history. If you have time, let Sunny take you around and soak in his history as one who has lived there for decades. A sort drive away is the Olveston House which serves great dinners. If you go, check out the photos done by Linda McCartney. Down the beach is Isles Bay Beach Bar and Restaurant. Odd hours, but great sunsets, drinks and dinners. Recommend reservations at both. The house is comfortable with an amazing pool. The views from the deck and pool are worth the visit. Great sleeping with the sound of the waves hitting the shore. The kitchen is well stocked. If you are cooking, the outdoor dinning is great. Recommend renting a car and exploring the island.
Top Guest favourite
Villa in Bolands
4.97 out of 5 average rating, 32 reviews

Unique Caribbean Secluded Open Air Villa 1 Bedroom

RobertRating, 5 stars2 weeks ago
This was our second visit to this home - it was as magical as the first. The house and view are stunning, proximity to Jolly Beach and Jolly Harbor mean everything you need is nearby. Susan took care of everything we needed prior to arrival and we had an amazing several days. Drinking coffee each morning we'd get fly-bys of tarpon, barracuda, eagle rays, sting rays, and a zillion other things in the crystal clear water. Could watch that all day long. Note: the listing is pretty clear on this, but it is a pretty good hike up and down the path to get from the road to and from the house - make sure you're good with that. But if you're on the fence, just book and have as much fun as we did.

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