
Villa holiday rentals in Cortona
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Top-rated villa rentals in Cortona
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Charming Villa in Val d'Orcia Tuscany, Great View
Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visit & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Poggio del Fattore-Villa with pool, hilltop, Chianti
Poggio del Fattore is situated at the eastern edge of the Chianti region in Valdambra, a green valley that joins the lands of Florence, Siena and Arezzo. The farmstead is on the top of an hill and lies at the end of a long private road through a large olive growing estate; therefore you absolutely need a car. The breathtaking landscapes and the location of the villa offer the privacy needed for a peaceful and relaxing holiday and a perfect departure point from which to explore central Tuscany.

Wine Experience Villa in Montepulciano
🏡 Villa Talosa è immersa nei vigneti della Fattoria della Talosa, storica azienda vitivinicola di Montepulciano produttrice di Vino Nobile. Un luogo autentico, ideale per rilassarsi con la magia della campagna toscana e una vista incantevole da ogni finestra. A soli 1,5 km dal centro storico, raggiungibile anche a piedi, potrete visitare la nostra Cantina Storica del 1500 sotto Piazza Grande: un’esperienza unica tra storia, passione per il vino. Riscaldamento e aria condizionata sono inclusi.

Villa i Cocciai - Villa i Cocciai
Over the years, Villa I Cocciai has been skilfully restored by the owners to give their guests greater comfort and at the same time leave the peculiarity of the Tuscan style intact. The villa develops on three floors and offers splendid views of the valley from its windows. The ground floor is composed of a large space that is dedicated to conviviality: here you will find a fully equipped kitchen (oven, dishwasher, fridge with freezer compartment, microwave, oven, Italian moka, American ...

Tuscan charm of villa - countryside
Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

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

A paradise in Montepulciano...
Villa Il Cubo is a full centralized air conditioned private house with large private swimming pool placed in the best garden spot for incredible views on the countryside around. Decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY!!!!!!

Stunning Tuscan Villa & Panoramic Infinity Pool
Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

San Giovanni in Poggio, villa Meriggio 95mq
Detached house, two double bedrooms, two bathrooms with shower, living room with fully equipped kitchen (dishwasher, washing machine, oven, microwave), double sofa bed, private garden with equipped pergola. Satellite TV and free Wi-Fi. Additional services at the property, upon reservation, include Focus brand Jarifa2 6.7 pedal-assisted bicycles and a wellness area with a Forest outdoor Finnish sauna and a heated mini-pool with hydromassage and chromotherapy with panoramic views.

Stone farmhouse in Val D'Orcia
19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.

Charming stone house with pool
This lovely house enjoys a special location, with breathtaking views of Lake Trasimeno, in the heart of the Montecastelluccio park, surrounded by woods, allowing you to stay in a dimension of great tranquility. Strategic because it is an hour or less from the main gems of Umbria and Tuscany, just to name a few: Perugia, Arezzo, Siena, Gubbio, Assisi, Spello, Montepulciano, Pienza, Cortona, San Gimignano and Città della Pieve. A unique experience

In a sunny, quiet and rustic area.
The villa is located between Anghiari and Arezzo in a sunny area, absolutely quiet, with a beautiful and panoramic view on the surrounding hills. Through the accurate restoration, the house is well equipped to ensure to just a few guests absolute confidentiality, independent and comfortable stay. Exposed to the south, with independent entrance and direct access to the garden that's exclusively for our guests. Please enjoy yourself.
Popular amenities for villa rentals in Cortona
Private villa rentals

Ortaglia di Sotto Farm

"Casetta" Panoramic Lodge in Umbria, Italy

Villa Il Tollino

Sestuccina

Country Charm & Jacuzzi

Country house in Cortona with swimming pool

Villa Fortuna with Hot-Tub and pool near Tuscany

Unique Villa in Tuscany
Luxury villa rentals

Vakantievilla Farmhouse Dolci Hills

Villa with panoramic pool • Lake Trasimeno

La Vignaccia (Farmhouse) - villa w/private pool

Riecine Capanna 4

Villa Cristina Tuscany,your dream!!

Villa unesco heritage, Jacuzzi & garden. BB Daria

Villa Poggio in Mandria in Chianti

Cosoli
Villa rentals with a pool

Magical Family Retreat

Beautiful Villa with Private Pool & Panoramic View

La Bacaia

Podere Biagio | Rural Tuscan farmhouse with pool

Private villa w/lake view & pool, VacaVilla Excl.

Beautiful tuscan country house

Villa "The memory of time"

Casa Baiocco Private Villa with pool and Jacuzzi
Destinations to explore
- Lake Trasimeno
- Lake Bolsena
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Uffizi Gallery
- Piazzale Michelangelo
- The Boboli Gardens
- Avignonesi Winery Fattoria Le Capezzine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Tenuta Le Velette
- Stadio Artemio Franchi
- Basilica di Santa Croce
- Basilica of St Francis
- Castiglion del Bosco Winery
- Teatro Verdi
- Cantina Colle Ciocco
- Teatro Tuscanyhall
- Santa Maria della Scala
- Furlo Gorge Nature Reserve
- Pubblico Palace
- Mount Subasio
- Casa Del Cioccolato Perugina
- Podere La Marronaia, Sosta alle Colonne
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore