10 World’s Prettiest Cliffside Towns

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Coastline, island, and mountain escapes on another level

From the quaint, quiet seasides of Greece and Italy to the bustle of Guanajuato, Mexico, you can’t beat the spectacular views when you give your vacation an altitude adjustment. If you’re inclined to take the term “hang out” literally, these cliffside vacation from around the world is sheer to please.

1. Oía, Santorini, Greece

If the hustle and bustle of Athens have you yearning for a place where life moves a little more slowly, this spacious villa overlooking the caldera that forms the island of Santorini is only a 40-minute plane ride away. Head out to the terrace and feel the tension melt away from your shoulders in the five-person Jacuzzi, or watch the village of Oía light up around you each night over a bottle of wine.

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Skirt the edge of the Santorini caldera from this ginormous panoramic Jacuzzi terrace!

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2. Uluwatu, Bali, Indonesia

Enjoy stunning surrounding ocean views, a spectacular private swimming pool, a spa terrace, and a wide variety of local cuisine with cool breezes and faint sounds of the waves crashing on Karma Beach directly below this tropical heaven on Earth. The locale is secluded yet convenient – it’s an easy drive to the beaches, golf courses, shops, and restaurants in popular areas such as Nusa Dua and Jimbaran – but we would just kick back at the pool and spa.

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Paradise on a cliff: a pristine, all-inclusive, crazily indulgent pool and spa villa

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3. Hawaii Kai, Honolulu, Hawaii

The Spitting Caves are one of the most well-known locations amongst cliff divers in Oahu. If you crave the rush of leaping from enormous heights into the sea, this cliff has got to go on your bucket list. Just, you know… stay safe. This magnificent island home is built on top of those very same Spitting Caves, so you won’t have far to travel to indulge your adrenaline junkie proclivities. The redwood house is designed with the views in mind, and you’ll find every room in the house delivers on that front. Whale watch right from your living room, or just hear the sea breeze sway the palms outside your bedroom.

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Get your adrenaline fix on top of Honolulu’s famous Spitting Caves!

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4. Clifton, Cape Town, South Africa

There’s not a window or door in this place that doesn’t look out onto a breathtaking vista. And although this home aims to provide you with an authentic cliffside living experience, you won’t have to wear yourself out getting there: you’re a brief jaunt from nearby Victoria Road, with very few stairs between you and the private pool on the veranda. Situated in Clifton, the affluent suburb of Cape Town, you’re only a 20-minute drive from the city center and attractions!

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A modern open layout bungalow where your cliffside pool is practically part of your living room

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5. Positano, Italy

Imagine being a scant 150 steps from your vacation home to one of the most beautiful beaches in the world. Well, it’s a reality at this southern Italian house. The terrace is the main attraction here: both bedrooms and the lounge open up onto the sunny outdoors, which provides a stunning seaside view. The picturesque village of Positano – a mere 40-minute drive from Sorrento – was featured in Under the Tuscan Sun, and Mick Jagger and Keith Richards purportedly wrote “Midnight Rambler” during their stay here.

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Go from bed to beach in 1 minute in a cliff and sea view Mediterranean home!

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6. Bonifacio, Corsica, France

Call up the whole squad. You’re all going to Bonifacio – at the southern tip of the popular mountainous Mediterranean island of Corsica. The owners of this space combined two large apartments into one to provide the perfect getaway for you and 7 of your family and friends. Antique furniture and period-appropriate renovation techniques ensure that you’ll have an authentic experience inside this old Corsican building, and uninterrupted views of the deep blue ocean on the connecting terrace outside.

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Massive cliff-top home with antiques and historical detail inside, endless ocean view outside

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7. Dubrovnik, Croatia

World travelers of the nerdy persuasion (our favorite kind) will know Dubrovnik as the Croatian city that HBO’s Game of Thrones transforms into King’s Landing and Qarth, and will soon know it as one of the locations featured in Star Wars: The Last Jedi. You won’t find a better place to stage your fantasy vacation than this beautiful apartment situated 490 feet straight above the sea, the architecture of which just screams King’s Landing. The house’s owner lives on site and can help out with any questions that may arise, and if your pup is a particularly enthusiastic fantasy fan, they won’t have to miss out on the fun too.

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Live like royalty in this century-old stone mansion in the top fantasy destination

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8. Ronda, Spain

The entire town of Ronda is built into the cliffs and steep hillsides of Andalucia. And if you come to Ronda, you must see Puente Nuevo, the 200-year-old stone bridge that spans the El Tajo gorge, a chasm wider than a football field, at its highest point and at the town’s center. When you’re done testing the limits of your tolerance for heights, take a 5-minute stroll back to this 2-story villa, where you’ll enjoy a dip in your private pool, and your view of Sierra de Ronda.

prettiest cliffside towns in the world

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Horseback riding, Spanish cuisine, and the legendary Puente Nuevo await the guests of this grand estate

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9. Vernazza, Italy

Some background for the uninitiated: the Cinque Terre is a set of 5 (the other 4: Corniglia, Manarola, Monterosso al Mare, and Riomaggiore) centuries-old seaside villages built into terraces and carved into the coastline of the Italian Riviera. It’s world-renowned for its intense natural beauty and colorful houses on steep cliffs. And it doesn’t get much more charming than this stone villa, where you’ll have an enviable top-to bottom view of the terraces of Vernazza when you’re not cuddled up and nursing a glass of wine by the wood-burning fireplace in the lounge.

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The best Cinque Terre experience: an old stone villa atop of a steep cliff with majestic vistas

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10. Guanajuato, Mexico

If isolation and peace and quiet don’t appeal to you like the rush and buzz of the city, this townhouse in the center of Guanajuato, an hour flight from Mexico City, might be more your speed. Thick windows throughout the house will insulate you from the noise of city life if you need a break, and a bedroom balcony, rooftop deck, and terrace allow you to experience the city without leaving your quaintly painted oasis. Don’t get too comfortable, though – you’ll want to take the 5-minute walk to Teatro Juárez, a triumph of both architecture and performance art.

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Cliff and the city: get the best of both worlds in this creative arts district townhouse

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What do you think of this awesome cliffside town?

Which Cliffside Town is on your bucket list?

♥Loreli

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