
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.

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

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.

[Cortona] Historic Villa with Pool and Park
Strategically located just 15 minutes from Cortona and Lake Trasimeno, this historic villa with private pool is the ideal place for those seeking charm and relaxation in the Tuscan countryside. • 3 double suites with private bathrooms • 1 single room in the turret • Fully equipped kitchen with dining area • Living room with fireplace and smart TV • Bright study with desk • 4 Bathrooms • Outdoor patio with dining table • Garden and swimming pool to relax 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.
Popular amenities for villa rentals in Cortona
Private villa rentals

Lake View Private Villa w Pool

Sestuccina

Country House Villa close to Perugia, Umbria

Tuscan villa in the heart of the Val d'Orcia

Podere Biagio | Rural Tuscan farmhouse with pool

Sasso Canaldo Elegante casale toscano

Villa Fortuna with Hot-Tub and pool near Tuscany

Casa Baiocco Private Villa heated pool and Jacuzzi
Luxury villa rentals

Magical Family Retreat

Casale La Querce-Tuscan Farmhouse with pool & view

CHARMING VILLA IN CHIANTI

Villa with panoramic pool • Lake Trasimeno

La Vignaccia (Farmhouse) - villa w/private pool

Villa with garden. The Cardinal's Garden.

Tuscany Villa With Pool & Magnificent Garden

Riecine Capanna 4
Villa rentals with a pool

Fontanaro/Sangiovese – Pool & Steps to Village

Villa Casanova - Private Pool & Garden in Umbria

Pasqui Villas : Tribbio private house pool WiFi

Villa with Pool Casa la Quiete

Country Charm & Jacuzzi

Montemarcoli

Beautiful tuscan country house

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




