Holiday rentals with a patio in Castiglion Fiorentino

The Eagle and the Olive Tree

At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

Outdoor spaces · View · Checkout

Tuscany Villa Mammi

Large, renovated stone villa in the woods of Castiglion Fiorentino, close to Cortona, Arezzo and Siena. A haven of privacy featuring a swimming pool, a panoramic hot tub with breathtaking views of the valley, and table tennis. Enjoy magical evenings under the stars, thanks to the authentic stone barbecue and the wood-fired pizza oven. The ideal getaway for those seeking relaxation, nature and comfort in the heart of Tuscany, perfect for families or groups dreaming of a truly unforgettable holiday.

Outdoor spaces · View · Amenities

Incredible Views & Pool in the Tuscan Hills

Fuggite nel cuore della Toscana e vivete un soggiorno immersi in dolci colline, una bellezza senza tempo e panorami indimenticabili. La casa offre l'accesso a una splendida piscina in comune e a tranquilli spazi esterni, perfetti per rilassarsi al sole o godersi serate serene. All'interno, troverete comfort, stile, tutto il necessario per un soggiorno memorabile. Ideale per coppie, famiglie o gruppi di amici che desiderano vivere un'autentica esperienza toscana a breve distanza in auto da Siena.

Outdoor spaces · View · Condition

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Outdoor spaces · Value · EV charging

Luxury Hilltop Villa | Infinity Pool, Sauna, View

Luxurious 5-Star Villa in Monte San Savino with heated Infinity Pool and breathtaking views of the Valdichiana Valley, ideal for families and groups of friends. Between Rome and Florence, it offers an exclusive and private experience with a large garden and elegant interiors. Relax by the fireplace, enjoy a BBQ, sauna, Wi-Fi, private parking, charging station, crib, high chair, and more. Immerse yourself in the sustainability of our Podere and discover Tuscany with activities and tastings!

Value · View · Decor

Breathtaking views: Historic House w/Terrace & BBQ

Welcome to our longtime family home — an elegant, light-filled space in the heart of Cortona. Set in a quiet historical square just steps from the main piazza. Enjoy spectacular views of the valley, lake and city. This elegant house blends the character of Tuscany with warmth and comfort. Antique terracotta beamed ceilings floors, a terrace with panoramic views, a house that tells a story. It's a space for travelers who appreciate beauty, stillness, and the atmosphere of an authentic home.

View · Pool · Accuracy

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Outdoor spaces · View · Cleanliness

Villa with Private Pool in the Tuscan Countryside

Modern villa with private pool, waterfall, large garden and relaxation area. Divided into: Suite with hydromassage bathtub, private bathroom and small refreshment corner; Apartment with 2 bedrooms, equipped kitchen and a second bathroom in elegant white faux marble. Perfect for families and groups up to 7. Features American BBQ, panoramic gazebo, ping pong, outdoor dining area and poolside shower. Close to Cortona, Arezzo, Montepulciano, Siena and the Crete Senesi.

View · Amenities · Comfort

Ancient Tuscan farmhouse in the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is on the first floor of the main farmhouse, with independent access and a tree-lined garden. Furnishings in the classic Tuscan style, with wooden beamed ceilings, terracotta floors that give a characteristic touch.

View · Value · Accuracy

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Value · View · Cleanliness

I Tramonti di Eramo, central Montepulciano.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

View · Value · Family

Pendici 15, small apartment

Cozy apartment inside a stone farmhouse where you can enjoy the atmosphere of the Tuscan countryside and at the same time the proximity to the historic center of Castiglion Fiorentino. Ideal for couples, families and travelers with four-legged friends, it is the ideal starting point to visit Tuscany. The accommodation combines the rustic charm of stone houses with modern comforts, offering a relaxing stay in a quiet and panoramic setting.

Outdoor spaces · View · Comfort