
Villa holiday 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

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.

[Cortona] Historic Villa with Pool and Park
Strategically located just 15 minutes from Cortona and Lake Trasimeno, this historic villa with a private pool is the ideal place for those seeking charm and relaxation in the Tuscan countryside. • 3 Double suites with private bathroom • 1 single room in the turret • Kitchen equipped with appliances and dining area • Living room with fireplace and smart TV • Bright study with desk • 4 Bathrooms • Outdoor patio with dining table • Garden and pool to relax in on the hottest days

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.

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.

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.

Villa in Montepulciano with a Pool
The Villa "I Girasoli" is part of the holiday farm "Il Serraglio" which covers 17 hectares. The Villa has a total area of 220 square meters that includes two bedrooms, two bathrooms, a large living room with an antique fireplace. Free WiFi. Direct access to the pool (which can be used by our other guests too) * Pool open from April to November. Circular heated pool, up to 32°C (90F) from May 1 to September 30 *
Popular amenities for Cortona villa rentals
Private villa rentals

Ortaglia Di Sopra Farm

Lake View Private Villa w Pool

Country House Villa close to Perugia, Umbria

Tuscan villa in the heart of the Val d'Orcia

Sasso Canaldo Elegant Tuscan farmhouse

The Lazy Oak

Luxury Tuscan countryside villa with pool/WiFi/AC

Beautiful tuscan country house
Luxury villa rentals

Casale La Querce-Tuscan Farmhouse with pool & view

Villa with panoramic pool • Lake Trasimeno

Villa with garden. The Cardinal's Garden.

Tuscany Villa With Pool & Magnificent Garden

Villa unesco heritage, Jacuzzi & garden. BB Daria

Villa Poggio in Mandria in Chianti

Villa Capanna, Private Pool, Breathtaking Views

Casa Faraona, villa with private pool
Villa rentals with a pool

"Casetta" Panoramic Lodge in Umbria, Italy

The House of the Sole del Sodo

Sestuccina

Villa with Pool Casa la Quiete

CHARMING VILLA IN CHIANTI

La Vignaccia (Farmhouse) - villa w/private pool

Montemarcoli

Special summer 2026 beautiful lake view pool relax
Destinations to explore
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Del Chianti
- Siena Cathedral
- Lake Bolsena
- Uffizi Gallery
- Eremo Di Camaldoli
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazzale Michelangelo
- Boboli's Garden
- Stadio Artemio Franchi
- Avignonesi Winery Fattoria Le Capezzine
- Basilica of St Francis
- Basilica of Santa Croce
- Teatro Tuscanyhall
- Teatro Verdi
- Mount Subasio
- Furlo Gorge Nature Reserve
- Palazzo Pubblico
- Cascate del Mulino
- Santa Maria della Scala
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore




