Holiday rentals in Pieve Caina

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Casale Monticchio - The Pigsties, up to 3 people

We created this 90sqm apartment from the old pigsties. Why they gave the pigs three beautiful south facing arched windows we still don’t know! The open-plan layout was designed to take into consideration wheel chair access as this is the only apartment on one level. The feeling is quite contemporary with one stone wall and the others being painted white. It is the most secluded of our apartments as it faces south onto the open fields toward Mercatello, where there is a nice bar run by Paola.

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

Residenza del 300 (Between Perugia and Lake Trasimeno)

Magnificent apartment located in a historic 14th-century building of Roman origin nestled in the heart of the Umbrian countryside, on a historic farm. The furniture is renovated and comfortable. Large, bright, functional space with an all-Umbrian view, surrounded by the vast vineyard, centuries-old olive groves, enchanting landscapes, large garden and other magnificent plants. 10 km from the historic center of Perugia and 10 km from Lake Trasimeno.

Best Luxury Stay Umbria/Tuscany/Lake Trasimeno

On the border of Tuscany and Umbria in the area of Lago di Trasimeno, Perugia, Assisi and Cortona, on the first floor, our spacious apartment of 200m2 is located in a beautiful ancient farmhouse "Casa della Civetta". On the border of Tuscany and Umbria in the area of Lago di Trasimeno, Perugia, Assisi and Cortona, our spacious apartment of +- 200m2 is on the first floor. Located in the beautiful centuries-old farmhouse "Casa della Civetta".

Agriturismo La collina degli Olivi

In Spina di Marsciano, nestled in the beautiful Umbrian countryside amidst fields of wheat, vineyards and olive groves, is the Collina degli olivi, a family-run agriturismo producing extra virgin olive oil, seasonal fruit and vegetables. We are strategically located, perfect as a base for exploring Assisi, Perugia, Orvieto, Todi, Gubbio, Lake Trasimeno and discovering the beauty the region has to offer. COORDINATES 42.978966, 12.268871

Beautiful Villa with Private Pool & Panoramic View

Escape to beautiful Umbria with our stunning villa rental. A beautifully restored traditional stone villa with panoramic views. We love the: 1. Spacious and beautifully restored villa. 2. Private pool and terraced gardens with panoramic views over Umbria’s rolling hills, forests, vineyards, and olive groves. 3. Some of the world’s best food, wine, art, and architecture on your doorstep.

Penthouse Vineyard Views on Countryside Estate

La Vista is our penthouse apartment with sweeping views and a romantic Romeo and Juliet balcony. Set on a luxury countryside estate with a panoramic pool, olive groves, and high-end amenities, it’s the perfect base to explore Umbria and Tuscany. We usually rent the full estate, so apartments like this are rarely available. If your dates are open, don’t wait—book your Italian escape now.

Suite Deluxe - Castello Monticelli

The guests can enjoy a unique and unforgettable experience by choosing between various luxury rooms and suites, all finely furnished and all with a spectacular view on the valleys around, and several comfortable and spacious apartments, all with Tuscan terracotta floors and with oak and chestnut beams and terracotta bricks on the ceilings.