Villa holiday rentals in Cortona

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Top-rated villa rentals in Cortona

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Guest favourite

Villa in Montepulciano

5.0 out of 5 average rating, 29 reviews

Terra Antica Suite & Villas - Montepulciano

Family Bio-Suite with 2 bedrooms, 2 bathrooms and a large living room with a comfortable double sofa bed. This Suite features an independent access and a panoramic view over the hills, a large patio with state-of-the-art outdoor furniture. The Suite Montepulciano has a fully equipped kitchen and direct access to the resort's swimming pool and jacuzzi. Towels and sheets are provided upon arrival along with a small cleaning kit for the kitchen. Recommended for 2 couples of friends, large families and groups. Air conditioning/heating and fast Wi-Fi available in all rooms. Located in Montepulciano, in the heart of the winery from which it bears its name, the newly built Resort Terra Antica offers air-conditioned accommodation and free Wi-Fi throughout the property. All the Suites and Villas that make up the Resort boast a large dining area, a seating area with flat-screen TV, kitchenette with dishwasher, oven, refrigerator and private bathroom with household linen. Furthermore, a free private parking is available to Guests. The Resort overlooks the beautiful Tuscan hills and is equipped with a spectacular infinity pool with outdoor jacuzzi and a very modern SPA overlooking the vineyards. A wonderful outdoor barbecue area is used for rich grilled dinners organized by the staff during the summer. The property is surrounded by 8 hectares of vineyards and a small enchanting cellar for the vinification and the aging of the company's organic wines.

8–15 Dec

€ 297 per night

Guest favourite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 166 reviews

The Villino Farmhouse

Entire upper floor of the newly renovated Villa Padronale in traditional Tuscan style. High ceilings with exposed beams make it cozy and perfect for families or groups of friends. In the house there are two functional large fireplaces(in the living room and kitchen). Private accommodation, not shared. The house has a large covered terrace,garden with sofas,bbq,firepit, private parking. The pool among the olive trees and vineyards is ideal for relaxing and has a private access to the shared area

31 Oct – 7 Nov

€ 492 per night

Superhost

Villa in Camucia

5.0 out of 5 average rating, 4 reviews

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.

18–25 Nov

€ 144 per night

Guest favourite

Villa in Castiglion Fiorentino

4.93 out of 5 average rating, 181 reviews

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

23–30 Mar

€ 393 per night

Superhost

Villa in Cortona

5.0 out of 5 average rating, 3 reviews

Villa Leopoldina, 6 pax, Private Pool

Magnifica nuovissima villa, tra Cortona e Montepulciano e a pochi minuti dal Lago Trasimeno. L’abitazione dispone di 3 camere da letto, ognuna con bagno privato, wi-fi, cucina perfettamente attrezzata e parcheggio privato. L'idilliaco giardino di 2000 mq, comprende querce, faggi, pini marittimi e una bellissima piscina privata in pietra grigia. Circondato da campi di girasole, vigneti e da boschi di querce e castagni, garantisce un assoluto relax e la massima privacy. Ideale per 6 persone.

13–20 Feb

€ 604 per night

Guest favourite

Villa in Siena

4.97 out of 5 average rating, 152 reviews

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.

13–20 Nov

€ 174 per night

Guest favourite

Villa in Montepulciano

4.95 out of 5 average rating, 116 reviews

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!!!!!!

9–16 Dec

€ 404 per night

Superhost

Villa in Siena

4.88 out of 5 average rating, 257 reviews

Fascinating Villa Senese with View!

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. Here time passes slowly according to ancient traditions. One of the most beautiful views that the Tuscan panorama can offer, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, original and working fireplace, parking free, WI-FI internet.

28 Oct – 4 Nov

€ 683 per night

Guest favourite

Villa in Cortona

5.0 out of 5 average rating, 52 reviews

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.

6–13 Dec

€ 538 per night

Guest favourite

Villa in Cortona

5.0 out of 5 average rating, 30 reviews

Casa Pietro Berrettini in Cortona

Casa Pietro Berrettini is located in the oldest and most characteristic district of the city of Cortona. Independent, immersed in an environment rich in history and culture, ideal for enjoying and extremely relaxing stays. Bright living area with panoramic terrace. Large private garden, very well maintained, overlooking the entire valley. Three bedrooms, each with en-suite bathroom and hot tub/shower, well finished detached apartment on the ground floor of the villa.

1–8 Dec

€ 159 per night

Guest favourite

Villa in Monticchiello

4.98 out of 5 average rating, 111 reviews

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

19–26 Mar

€ 609 per night

Guest favourite

Villa in Cavriglia, Arezzo

4.99 out of 5 average rating, 110 reviews

Villa Poggio a Mandria in Chianti

Villa Poggio a Mandria is the gateway to the Chianti; it is a good base to reach the most beautiful art cities of Tuscany (Arezzo, Florence, Siena, San Gimignano, Volterra) in about one hour time. On the surrounding hills there are medieval villages, which offer visitors a charming atmosphere of the past and the opportunity to take walks in an unspoiled countryside.

11–18 Oct

€ 666 per night