
Villa vacation rentals in Cortona
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Top-rated villa rentals in Cortona
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Cottage in Val d'Orcia Tuscany, Jacuzzi & Hot Tub!
Welcome at Charming Cottage in Tuscan Villa! Immerse in the history of Montepulciano, Pienza, Cortona, Siena, Explore Val d'Orcia, natural hot pools and falls! Fully equipped kitchen, private patio for al fresco dining, magnificent bathroom with large Jacuzzi, and large bedroom with new top quality, Memory foam mattress. Thanks to thick walls, it's very cool in summer! We arrange Winery tours & tasting and cooking class. A/C, Free wifi, comfy sitting and sofas and Hot Tub with great view!

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.

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

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.

Villa Il Tollino
Villa Il Tollino rises on the hills surrounding the Valdichiana just a few kilometers from the most beautiful villages of the south Tuscany such as Montepulciano, Pienza, Siena, Arezzo and San Gimignano. The panoramic position makes this villa surrounded by greenery, an ideal place to relax, take long walks and taste the best wines of the area. The large fenced garden, the terrace, the patio and the small cottage inside the property is a place suitable for families with children.

A paradise in Montepulciano...
Villa Il Cubo has a large private park and swimming pool and marvellous views on the Tuscan countryside. It is fully air-conditioned and the decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point at a moderate extra contribution. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY.

CHARMING TUSCANY VILLA PRIVATE POOL
Antico casale rurale, situato sulle colline Toscane con vista sulla campagna circostante . Isolato e ideale per chi desidera rilassarsi ma vicino alle principali città turistiche italiane. Ogni camera è dotata di condizionatori con tecnologia windfree, nel salotto è presente una TV 82" ULTRA HD con SKY e canali internazionali. La piscina è dotata di illuminazione Philips Hue per creare l'atmosfera giusta in ogni momento e di impianto audio Bose Soundtouch bluetooth

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.

Villa unesco heritage, Jacuzzi & garden. BB Daria
Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant

Tuscany View - Villa Arianna
This beautiful villa, which can accommodate up to ten (10) people, will provide an unparalleled Tuscan experience. While positioned perfectly to allow easy access to the most beautiful towns and villages of southern/central Tuscany (such as Arezzo, Florence, Siena, Cortona, Montepulciano) and northern Umbria (such as Perugia, Orvieto, Assisi); you’ll find this villa offers complete privacy as well as a sense of peace and tranquility to all who visit.
Popular amenities for Cortona villa rentals
Villa rentals with a pool

Ortaglia Di Sopra Farm

Casetta I Ciliegi

Lake View Private Villa w Pool

Casa del Sole 4, Emma Villas

Villa with panoramic pool • Lake Trasimeno

Exclusive holiday home with spectacular lakeview

Villa la Chiusa- con piscina e aria condizionata
Wp Relais Villa Vignalunga
Private villa rentals

Friscello | Stone Mill Retreat in the Tuscan Woods

Villa I Cipressini Tuscany Private luxury pool spa

Country Charm & Jacuzzi

Podere Biagio | Rural Tuscan farmhouse with pool

Montemarcoli

Agriturismo Henni panoramic pool sauna and jacuzzi

Villa il Palagio in the Tuscan countryside

Chianti Villa | Garden & Panoramic Pool
Luxury villa rentals

Fabulous Farmhouse with Pool & 360 Panoramic View

Villa Casanova - Private Pool & Garden in Umbria

Casale La Querce-Tuscan Farmhouse with pool & view

Villa in Montepulciano with a Pool

La Vignaccia (Farmhouse) - villa w/private pool

The Lazy Oak

Villa "The memory of time "

Villa Cristina Tuscany,your dream!!
Destinations to explore
- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Del Chianti
- Lake Bolsena
- Eremo Di Camaldoli
- Great Synagogue of Florence
- Cascate del Mulino
- Uffizi Gallery
- Piazzale Michelangelo
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Boboli's Garden
- Stadio Artemio Franchi
- Avignonesi Winery Fattoria Le Capezzine
- Basilica of St Francis
- Basilica of Santa Croce
- Teatro Tuscanyhall
- Teatro Verdi
- Furlo Gorge Nature Reserve
- Mount Subasio
- Palazzo Pubblico
- Santa Maria della Scala
- Ugolino Golf Club
- Rocca Maggiore
- Siena Cathedral




