
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!

Historic Villa Getaway with 6BR/9BA, Pool, Views
This six-bedroom villa complex, set in atop a hill, overlooks a panorama of surrounding hills, fully immersed in nature. Villa was estored in 2020, with the rustic flair preserved to maintain its unique charm. The authentic stonework, the open fireplace in the entrance hall, and the exposed beams are in harmony with wooden floors. The villa is within 30min drive of Cortona. Also near Siena, Gubbio, Assisi, Lake Trasimeno, Arezzo, Montepulciano, Spoleto, and Perugia. (Read other details to note)

Apt. Rolando-Tenuta VillaAugusto
La struttura è ubicata in un agglomerato distante 3/4 km dal centro di Cortona. Circondata dal verde, un vero paradiso di tranquillità. Alloggio indipendente e accogliente con ampi spazi arredati con mobili e oggetti d'epoca, cucina attrezzata, camera da letto, biliardo e sala Pianoforte. Ambienti climatizzati. Spazio esterno attrezzato con tavolo, sedie e lettini. Ampio parco con molti spazi ombreggiati e grande piscina (14x7) immersa nel verde, condivisa con gli altri ospiti della tenuta.

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

Fattoriafontenovo, country house Perugia Umbria
Welcome to our charming apartment in Fattoria Fontenovo in Umbria fresh hills !This cozy retreat at our historic Fontenovo Farm, owned by our family for over 100 years, offers the perfect blend of privacy and tranquility. Some areas of the spacious villa remain unoccupied and others are reserved for your use. During the stay, you'll be the sole occupants, apart from the owners who may occasionally be in another part of the house. Enjoy the lush gardens, private pool, and serene countryside.

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

Virgi House
Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

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.

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

Casetta I Ciliegi

Lake View Private Villa w Pool

Casa del Sole 4, Emma Villas

Villa with panoramic pool • Lake Trasimeno

Country house in Cortona with swimming pool

Villa il Palagio in the Tuscan countryside

Poggio del Fattore-Villa with pool, hilltop, Chianti

Villa il Laghetto with Infinity Pool in Tuscany
Private villa rentals

Friscello | Stone Mill Retreat in the Tuscan Woods

Elf Hut

VILLA ROSETO-TODI

Country Charm & Jacuzzi

Ancient tower w/ private pool Vacavilla Exclusive

CHARMING TUSCANY VILLA PRIVATE POOL

Villa with garden. The Cardinal's Garden.

Villa Fortuna with Hot-Tub and pool near Tuscany
Luxury villa rentals

Fabulous Farmhouse with Pool & 360 Panoramic View

Casale La Querce-Tuscan Farmhouse with pool & view

La Vignaccia (Farmhouse) - villa w/private pool

The Lazy Oak

Podere Biagio | Rural Tuscan farmhouse with pool

Villa "The memory of time "

Agriturismo Henni panoramic pool sauna and jacuzzi
Wp Relais Villa Vignalunga
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




