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Vacation rentals in Lookout

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Popular amenities for Lookout vacation rentals

Other great vacation rentals in Lookout

A tranquil evening view captures a private swimming pool reflecting soft colors of the sunset. The spacious outdoor area transitions seamlessly to the villa, which is illuminated from within. Lush greenery surrounds the villa, enhancing the serene atmosphere near the Caribbean Sea.
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.
A serene pool area is featured, showcasing a main swimming pool surrounded by a spacious deck. Colorful lounge chairs are positioned nearby, and a whirlpool is integrated with natural stone accents. Lush greenery and clear skies provide an inviting backdrop for relaxation.
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!)
A sparkling private pool is surrounded by lush greenery and features a tiled deck. The expansive view of the ocean is visible in the background, enhancing the serene setting. Sun loungers are placed near the pool, inviting relaxation in the sun.
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.
An outdoor courtyard area is shown, featuring a swimming pool surrounded by lush greenery. Two guests are seated at an outdoor kitchen bar, enjoying the evening ambiance. A dining area with an umbrella is visible along with two red lounge chairs, providing a relaxing spot near the pool.
Apartment in Cudjoe Head
4.73 out of 5 average rating, 15 reviews

Cozy Fully Equipped Apartment w/Jeep Rental

HeatherRating, 5 stars2 weeks ago
Very nice apartment with AC in the bedroom. Kulcha was a great host. We appreciated his flexibility and refunding us for the days we couldn’t make it because we missed our flight to Montserrat. Would stay here again.
Guest favorite
A balcony overlooks a scenic view with soft hues from a setting sun. Two white chairs and a small table create a cozy seating area, framed by blue walls and white railings, enhancing the connection to the surrounding natural landscape.
Guesthouse in Old Town
4.88 out of 5 average rating, 51 reviews

Blue Lime Cottage

AdrianRating, 5 stars2 months ago
Our Time in Montserrat was Great and Peaceful. This property really gives you the great views and sounds of the ocean when you wake-up, and the outdoor/indoor living with the sliding glass doors. The very cozy cottage provides all the necessities as a visitor in Montserrat. I would definitely recommend this location and Montserrat for your next stay for peace and tranquility. - PAO
A private pool is situated beside a sun terrace, featuring lounge chairs under a large umbrella. Lush palm trees frame a panoramic ocean view, with gentle waves visible in the distance. The clear blue sky enhances the tranquil outdoor setting.
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.
A serene pool deck features a rectangular swimming pool reflecting the colorful sky at sunset. White lounge chairs are positioned around the pool, facing the ocean view, with tree silhouettes in the background, enhancing the tranquil atmosphere of the location.
Villa in Garibaldi Hill
4.77 out of 5 average rating, 26 reviews

Isles Bay Villa

JamesRating, 5 stars2 months ago
A beautiful villa with the most picturesque views. A heavenly garden in which me, my husband and our three children spent time in appreciating the plants and animals! A humming bird and an iguana amongst the most colourful geckos set in a beautifully kept garden, with roosters roaming freely bringing music to the area. Manual present in the house and even a guest book to leave comments in. The kitchen was very well equipped and a laundry area, super convenient. So many towels and linen! Super convenient when using pool. The house itself has mild wear and tear. WiFi was readily available. The home looks and feels loved, decorated with lots of wall hangings and homely touches. We would definitely book this place again, no questions. Beautiful home.
Top guest favorite
An open-air pavilion overlooks the calm sea, featuring a large infinity pool with a wooden deck. A single blue bean bag chair rests on the edge, facing the expansive horizon. Lush palm trees frame the serene view under a clear sky with distant clouds.
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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