Effortless luxury meets island living

Location, location, location, they say. Well, The Lookout on the Isle of Portland is so well-located, you’ll think you’re cruising the seas. Above the endless roar of the waves and beneath the squawk of the gulls, sit in peace with a G&T and enjoy some R&R where effortless luxury meets island living.

Oceans of simply luxury

If location, location, location is everything in property, then The Lookout is where it’s at. Right at the end of England, on the Isle of Portland, The Lookout is so much a part of the breaking waves and the cawing gulls, you’ll feel like you’ve joined the Navy.

Fortunately, this is one mission you won’t need to press-gang five of your nearest and dearest to sign up for. The Lookout is an exercise in effortless luxury with a panoramic balcony that begs for a sundowner above the roar of the ocean.

Rustle up some fresh lobster, set the wine to chill, then fling open the terrace doors and dine al fresco in the ocean air as you track the boats that trawl across the harbour and watch the sun glint off the surf.

The bedrooms are a statement in simple luxury, the kitchen sits primed for warming roasts in winter and crisp salads in summer, but it’s the views that stay with you. Back in the office, the sound of the surf and the smell of the briny will get you through the working week.

Terrace and views

Close your eyes and listen to the squawking seabirds and the low rumble of the ocean and you could be on the deck of a cruise ship. Open them, see the panorama play out towards the blue horizon and you’re still on that ship.

After a day in the sea air, embrace the breeze, soak up the sun and sit back on The Lookout deck as the steaks sizzle and the glasses clink. There are no dark clouds on the horizon – just boats and birds in the ultimate seascape.

If the clouds do part, double French doors take you back indoors to the open-plan, washed-wood living and dining area. Break out the cards, make with the charades, get the kettle on, plump up the cushions. You’ll be back out in the sun soon enough.

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Living Spaces

There’s plenty room for six here, but you’d be forgiven for living life on deck, where the Isle of Portland views rush up to greet you in extra-wide Cinemascope.

Inside, the open-plan kitchen, dining and living area is the heart of the home. It’s the venue for hearty roasts in winter, salads in summer, and happy chat and laughter and card games before bedtime.

After a day on or under the sea, there’s a dry room for water sports equipment and even space to park your boat.

Cooking and Dining

You might be inspired by the sea air and the views to rustle up a roast or a lamb tagine, and the decking is crying out for a barbie sloshed down with sundowners, but if you want to step down, we can step in.

Just whistle and our chef and maid will be right there to create special cuisine for a celebration, or put your feet up, pop a cork or two and enjoy a fully catered holiday. Also on the menu, we can arrange local gourmet food hampers or bespoke fine wine. Just say the word.

Out and about, nothing beats steaming-hot fish and chips on the harbour wall, unless it’s Michelin-starred dining at Dorchester’s Sienna. Weymouth harbour’s the spot for great gastro dining, and there are pubs just a stagger away for hearty bar meals and real ale.

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Sleeping six in simple luxury with one en-suite, The Lookout will lull you into the deepest of slumbers.

The three bedrooms here are as crisp and fresh as the ocean breezes that blow in though the open windows to ripple the curtains and flutter the heart.

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What people say

What people say

“We loved our stay at The Lookout, the kids enjoyed island life, exploring the quarries and trying their hand at some kitesurfing. The views were unbeatable and the seafood at the Crab House Café was some of the best we’ve ever had!” - Fran
“The Lookout is perfectly located on the island of Portland which means that we were nicely nestled away along the coast. Weymouth is just a short drive away so there is plenty to do in the way of ice creams and sandcastles too.” - Ollie
“A quick message to say what a wonderful time we had at The Lookout - our new dream home! Everything inside is completed to a high standard and the rooms are spacious and light, and the views of the sea are absolutely perfect!” - Naomi

Get the most from the coast

Explore the Jurassic Coast with crabbing or coasteering. Fish for mackerel, walk for fun. Spot seals and dolphins in the surf. Eat heartily with fish and chips on the harbour wall, Michelin-starred dining, or summon up a chef back at base.

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