Luxury Hilltop Retreat

Two Villas that can be rented independently

Located on a secluded hilltop in the Le Marche region, you and your guests can relax and reset on an 3,5-hectare estate whilst enjoying views of rolling hills, olive groves, vineyards and the Adriatic Sea. A noted Traveller Made Private Place and recommended by famed author, Frances Mayes in her new book ‘Always Italy’, Castelletta Estate includes two Villas – Villa Olivo and Villa Oliveto. Designed with luxury in mind, each with their own garden, gym, swimming pool, along with spacious indoor/outdoor living areas.

The Villas are connected via their gardens with a state-of-the-art studio overlooking olive groves nestled in between – creating the
ultimate retreat, holiday or experience.

Book both Villas for up to twenty-two guests or separately with Villa Oliveto sleeping eight and Villa Olivo sleeping fourteen.

The experienced concierge team offer exceptional custom services, authentic experiences and itineraries. From outdoor experiences such as truffle hunting and sailing to in-villa activities such as massage, cooking classes and sound healing – the options are endless.

With its clean, quiet beaches, breathtaking mountain ranges and charming historic towns untouched by tourism, Le Marche ticks all the boxes for those seeking an authentic retreat.

Villa Olivo

Beautifully designed and newly renovated, Villa Olivo is an unrivalled luxurious Italian villa overlooking the stunning coastline of the Adriatic Sea. A hilltop retreat offers year-round exceptional luxury, 5* services and authentic experiences in the heart of Le Marche. Set amidst rolling hills, olive groves and ancient vineyards and just 10 minutes from the coast, Villa Olivo has been beautifully crafted to the highest standards, with 6 King-size ensuite bedrooms plus an attic ensuite sleeping two, its own spa, gym, infinity pool and over 600 m2 of living space.

The White Glove service can help you relax at home, whilst our tailor-made experiences are designed around your needs…. all you need to do is ask.

Your very own Italian home from home, Villa Olivo is the perfect destination for an exclusive escape for up to 12 + 2 people (6 bedrooms + attic ensuite).


Each of Villa Olivo’s six large, blissful double bedrooms have been crafted and design with its own personality. All equally spacious and well- appointed with en-suite bathrooms and a private terrace or balcony complete with panoramic views of the surrounding hills and Adriatic Sea.

Kitchen & Dining

Designed for the real foodie, Villa Olivo has the most incredibly appointed kitchen and is donned with many inspiring indoor and outdoor eating spaces as well as a huge gas barbeque. So, whether you want to cook for yourself, fancy a cooking lesson or would like a local chef to cook for you instead, all you have to do is make the choice…

Living Space

Designed to be your home-from-home where you can relax, play and eat in true Italian style. Villa Olivo is a rare mix of open plan living with several secluded spaces, inside and out, where if you want to get away from it all, you can have uninterrupted time away.

Spa, Gym and Pool

This all-year-round villa has a huge infinity pool overlooking the beautiful views of olive groves and the Adriatic Sea. The indoor spa is beautifully appointed with a 6-seater jacuzzi, a steam room, sauna and a shower ‘emotional’ (with scented water) helping you achieve ultimate in relaxation, even in the winter months, or workout in the fully equipped fitness centre with stunning sea views and the latest Technogym equipment.

Villa Oliveto

Set amongst rolling hills and ancient vineyards, the luxurious Villa Oliveto comes with more than three hectares of the Oliveto estate filled with manicured gardens overlooking its very own 400-tree olive grove. With uninterrupted views of the Adriatic coast and untouched Italian landscape, here you will enjoy the slow way of life, and once you have entered the 50-meter-long driveway lined with olive trees, you won’t want to leave. This 4 bedroomed luxury villa is only just the start, because once you start to explore you will find multiple outdoor eating areas, many private corners to relax and restore, a huge architectural pool house & gym, with a 21m outdoor pool, a tennis court amidst the olive grove and our new purpose-built yoga studio that overlooks it. The 24/7 concierge team can craft bespoke experiences to tailor make your stay, designed around your needs. Your very own Italian home-from-home, Villa Oliveto is the perfect destination for an exclusive escape for up to eight people.


Villa Oliveto has four beautifully designed and luxuriously appointed double ensuite bedrooms. Three are within the villa itself, and the very beautiful annex bedroom sits just outside of the villa, perfect for those who want a little of their own privacy. Each of the spacious bedrooms have its own look and feel, yet all with the 5* comforts you would expect of the oliveto estate. Decorated in calming, natural hues, each ensuite bedroom has fantastic natural light and features a variety of views from the spectacular olive grove, to the sea view or the beautifully manicured gardens.

Pool, Pool House, Pagoda, Gym & Tennis Court

An architect’s dream, and a traveller’s delight. A good 100 metre walk down a path from the villa, overlooking the sprawling olive grove, you will find the beautifully designed grounds of the pool house and the twenty-one by 6 metre pool. The luxury, spacious, modern pool house is a concrete minimalist haven from the sun, housing a kitchenette, bar, eating area, gym, two washrooms and two showers. The pool house comes complete with retractable floor-to-ceiling windows so if you would like to use this as a yoga studio in the winter or summer months, you can.

Kitchen & Dining

Villa Oliveto is the perfect location for those who love to cook, entertain or for those who would like to be cooked for during any month of the year. With four spacious dining areas and two kitchens to choose from, complete with a huge traditional wood-fired pizza oven, the villa is a foodie’s dream destination.

Living Space

Villa Oliveto has been designed with entertaining in mind with its light, airy and relaxing open plan living space. Expansive views can be enjoyed from the large windows that wrap around the south facing side of the villa where you can lose yourself in the rolling hills and olive groves that extend to the sea.

White Glove Service

If you want your holiday to be surrounded by total relaxation, our concierge service is available to make you feel at home; be that pre-stocking the pantry, fresh towels laid out by the pool, booking you in for a massage or organising a trip to the local beach.

Yoga Studio

Open for use for both Olivo & Oliveto guests on request, the studio is your calming, flexible space that overlooks their very own olive grove, and the sea. This year-round space has been purposely designed to benefit from both natural light, mood lighting and a connected sound system, so when the time has come to relax and restore after a long practice, you can create the most calming environment. Just in front, enjoy both sunrise and sunset on our yoga deck, nestled between two olive trees.

And just to make your life even easier, they have all the necessary equipment there for you too, along with a water machine and facilities, so you don’t even have to think about it.

Property Features

  • Air Conditioning
  • BBQ
  • Dishwasher
  • Swimming Pool
  • Tennis Court
  • Washing machine
  • Wi-Fi

Rental Information

  • Check In4:00 PM
  • Check Out10:00 AM
  • Max Guests20
  • Min Stay4
  • Security Deposit€1500