Castle holiday rentals in Tuscany

Historic 8th-century residence with panoramic pool

Experience the thrill of sleeping in a real 8th-century castle in the heart of Umbria. The Dependance, in the historic part of the Castello del Cardaneto, is a 50-square-meter studio apartment with a separate entrance, a double bedroom, a living room, and a bathroom. Nestled in a 4,000-square-meter park, the Castle offers a panoramic swimming pool with a spectacular view of Montone, one of the most beautiful historic towns in Italy. An authentic historic residence, where history, nature, and relaxation meet (no kitchen but a well-stocked bar area)

Location · Family · Pool

Proceno Castle, Loggia Apartment

Apartment of 65 sqm for 2 people, inside the medieval courtyard of the Proceno Castle, with private entrance, large living room with working historic fireplace and kitchenette, 1 double bedroom located on a mezzanine from which the living room dominates, bathroom with shower stall, veranda with stone and wood porch, in typical medieval style, which leads through stone stairs to the inner courtyard of the Castle, from which guests have access to the village and the rest of the courtyard accommodations.

Location · Family · Amenities

XIII Century Tower with Private Panoramic Pool

Ancient country tower property with 5 airconditioned bedrooms for up to 10 guests at the heart of the peaceful Montechiaro organic wine estate. From your private pool, soak in the Tuscan sun and enjoy unforgettable views of the Chianti rolling hills and the medieval towers of Siena. The property also boasts access to the endless olive grove, a large patio area for outside dining in the shade, ping pong table for fun family matches, WIFI & free parking. Silence and time are the real luxury here.

Location · Family · Beach

Medieval TOWER in Italian Burg of 1200 (UMBRIA)

Imagine yourself enjoying a breathtaking view from the top of a medieval tower. This is only one of the experiences you'll collect during your stay. Add attention to details, fireplace, pool and olive trees: you've found the recipe of a very special vacation. And outside, Umbria is ready to welcome you with its history, spirituality and food. If you're looking for an exclusive experience surrounded by peace and nature, you're in the right place. We do the same since 1990 and it's never enough.

Value · Location · Walkability

Trasimeno Lake - "The Convent"

On top of a hill of centuries-old olive trees on the southern shore of the Trasimeno stands LA BADIA DI S.ARCANGELO. In this unique and precious place is the apartment "Il Convento" which will welcome you with its warm atmosphere and a welcome gift with local products. It can accommodate up to 5 people and consists of a dining kitchen, a living room with a comfortable sofa bed, a double bedroom, a single bedroom and a special bathroom created in what used to be the bell tower of the Abbey.

Location · Family · Walkability

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Value · Location · Sleep quality

Tower Penthouse in small castle near Florence

900 year old Tower-Penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, history, convenience. (AC throughout). Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.

Value · Location · Backyard

La Piccola Badia

Unique place just a few minutes' drive from Siena. Apartment with garden located in an old 12th-century abbey and transformed into a fortified castle by a noble Sienese family in the 16th century. The apartment located on the ground floor is complete with a kitchen, a living room with a sofa bed, a double bedroom, and a bathroom. Tiled outdoor space with gazebo and outdoor living area and a charming garden with olive trees and flowers.

Family · Location · Decor

at the castle of Montacchita stunning view

A JEWEL IN THE HEART OF TUSCANY A unique and romantic bijoux cottage with a magical atmosphere and breathtaking views of the valley, with a large garden and private access, renovated in a rustic style within an ancient medieval fortress. A strategic location for visiting the best attractions: Pisa, Lucca, Florence, San Gimignano, and Siena, just 40 minutes from the sea.

Location · Family · Indoor spaces

Castello delle Serre – Private Villa

Our Private Villa is located on the grounds of Castello delle Serre, owned and operated by Italian-American family and staff. Castello delle Serre sits at the top of Serre di Rapolano, an unspoiled Tuscan village with the easiest access to all of the major points of interest. Siena, Chianti, Montepulciano, Montalcino, Cortona and Arezzo are only a short drive away.

Location · Family · Hospitality

Castle of Montegiove, La Casetta

Charming apartment located just outside the ring wall of Castello di Montegiove. Montegiove is a lovely and peaceful medieval country village, close to the main communication lines and equidistant of Rome (154 km) and Florence (151 km), an ideal base for exploring the historical treasures of Umbria and Tuscany, such as Orvieto, Todi, Spoleto, Perugia and Siena.

Family · Location · Walkability

Suite in Castello di Valle

A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.

Family · Value · Kitchen