Luxury hilltop retreat with five-star services in Le Marche

Castelletta Estate is a luxury retreat in Le Marche. Poised high on a hill in Le Marche, with rolling views of olive groves, vineyards and 10 minutes from the Adriatic sea, Castelletta Estate is designed to the highest standards, stylishly decorated and completely renovated by an Italian-English entrepreneur couple. Sporty guests also have access to the tennis court, a fully equipped gym or can fully relax in the purpose-built yoga studio.

The Estate includes two villas, Villa Olivo and Villa Oliveto, both of which are distinctly designed with their own separate garden, gym, swimming pools, studio, and inside and outdoor living areas. Both villa’s can be interconnected via their garden’s to create a retreat, holiday or experience for up to 20 guests plus 2 retreat hosts (22 in total). Castelletta Estate can also be booked separately with Villa Oliveto sleeping 8 and Villa Olivo sleeping 12 guests.

This hilltop luxury retreat offers tailored year-round exceptional luxury, five-star services and immersive experiences for up to 22 people. The experienced concierge team can organize tailor-made authentic experiences such as truffle hunting, cooking classes, and wine tastings. But also bookings at Michelin star restaurants, shopping trips to designer stores, and active excursions such as fishing, sailing, and hiking are an option. These activities can be booked prior to your stay.

The luxury retreat has also recently received quite a bit of publicity, with mentions in Elle Decor Italia and Epoch Times, and recommended by the award-winning author of Under the Tuscan Sun, Frances Mayes as a place to stay in her new Always Italy guide.


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-star 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).

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 and 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.


  • 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.


  • Villa Olivo pool heating: € 600,- (please note this may vary due to oil prices). It takes 3 days to reach 25-28 degrees celcius and temperature is weather dependent. 48 hours notice is needed.
  • Tourist tax: € 32,- per person for the stay.
  • Mid week housekeeping: € 400,- (it includes towel refresh, communal areas, spa, and bedrooms, but excludes sheet change).
  • Daily studio clean: €150,- per stay.
  • Concierge: check in, check out, and regular pop in’s are included, if you require a full time concierge, we can quote on booking.
  • Any extra requests: will can be quoted on request.


  • Ancona Airport: 35 minute drive
  • Adriatic sea: 10 minutes drive
  • Macerata: 30 minute drive
  • Loreto: 22 minute drive

What to do?

The luxury retreat of Castelletta Estate is located in the heart of Le Marche, which has recently been called out by Forbes, The Telegraph, The Epoch Times and The Guardian as being the new Tuscany without the crowds and a must-see region in 2020. 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.

Property Features

  • Air Conditioning
  • BBQ
  • Dishwasher
  • Gym
  • Jacuzzi
  • Spa
  • Swimming Pool
  • Tennis Court
  • Washing machine
  • Wi-Fi
  • Yoga studio

Rental Information

  • Check In4:00 PM
  • Check Out10:00 AM
  • Max Guests22
  • Min Stay4
  • Cleaning Fee€800
  • Security Deposit€3000

Book this listing

Price per weekVilla OlivioVilla OlivetoCastelletta Estate
No. persons14822
06.01.2024 - 18.05.2024€ 9500€ 6000€ 15500
18.05.2024 - 22.06.2024€ 13000€ 8000€ 21000
22.06.2024 - 07.09.2024€ 15000€ 11000€ 26000
07.09.2024 - 12.10.2024€ 13000€ 8000€ 21000
12.10.2024 - 21.12.2024€ 9500€ 6000€ 15500
21.12.2024 - 06.01.2025
29.03.2024 - 06.04.2024
€ 11000€ 7000€ 18000