Vacation rentals in Montecchio

Tuscan charm of villa - countryside - Villa Senaia

In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas

Location · Value · Access

Nonna Nesti Vacation Home

Our vacation home is located in Cortona, a few kilometers from Arezzo, Siena, Perugia, Assisi, Montepulciano and Lake Trasimeno Ideal for food and wine and cultural tours In addition to the large panoramic terrace where you can relax and admire the stars but also dine outdoors, you will be welcomed by a large living room, dining room with fireplace and kitchen as well as two large bedrooms. It will also be pleasant to relax in the large garden where you can spend moments of serenity and tranquility.

Value · Family · View

Villa Le Vigne, 8 pax, private pool, Top Comfort

Magnificent Tuscan farmhouse totally restored, very close to the beautiful towns of Cortona and Montepulciano and minutes from Lake Trasimeno. The house has 5 bedrooms, each with its own private bathroom, powerful wi-fi, large kitchen, fireplace, private parking and study. The garden of 2500 square meters, includes a beautiful private pool. Surrounded by 30 hectares of vineyard and oak and chestnut woods, it guarantees absolute relaxation and privacy. Ideal for 8/10 people. Pool open fm 1st Apr

Family · Value · Indoor spaces

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.

Value · Location · Bathroom

Rural Tuscany | Family farmstay with restaurant

Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

Family · Location · Kitchen

Fabulous Farmhouse with Pool & 360 Panoramic View

In the very centre of Italy, straddling the border of Umbria and Tuscany, this carefully restored farmhouse makes a great base for a memorable Italian holiday. Situated in an idyllic hillside position overlooking Montepulciano, ‘La Colomba’ is blessed with 360-degree views of iconic Italian landscape and fully equipped with all child amenities. Within easy reach of many of the world’s most important historical and cultural attractions, this house really is The Italian Dream.

Location · Family · Shared spaces

Rural Tuscany | Farmstay with pool & garden

The Tuscan estate Terra di Cortona lies in a strategic position between the beautiful Tuscan town of Cortona and the Trasimeno lake. The farmhouse consists of five spacious apartments and has a history that goes back to the late 17th century, when a noble family built it as a holiday residence. Air conditioning is available, as well as satellite television and Internet access. In the garden of the property there is a pool with solarium, barbecue and volleyball field.

Location · Value · Outdoor spaces

Villa with Private Pool in the Tuscan Countryside

Modern villa with private pool, waterfall, large garden and relaxation area. Divided into: Suite with hydromassage bathtub, private bathroom and small refreshment corner; Apartment with 2 bedrooms, equipped kitchen and a second bathroom in elegant white faux marble. Perfect for families and groups up to 7. Features American BBQ, panoramic gazebo, ping pong, outdoor dining area and poolside shower. Close to Cortona, Arezzo, Montepulciano, Siena and the Crete Senesi.

Family · Location · Decor

Il Giardino degli Ulivi | Casa Ippocastano

Il Giardino degli Ulivi is a farmhouse in the heart of Tuscany, surrounded by olive groves and only 3 km away from the charming town of Cortona. The property features 6 restored farmhouse apartments, each offering authentic Tuscan character, modern comforts, and private outdoor spaces. Guests can enjoy peaceful garden, scenic views, and relax by the swimming pool, as well as easy access to Tuscany’s rich history and vibrant cultural offerings.

Family · Value · Quiet

Villa Bellora | Pool & Panoramic Views | Cortona

Villa Bellora: Your Tuscan Summer Escape Perched among Tuscany's rolling hills and vineyards, Villa Bellora sits 20 minutes from both Cortona and Montepulciano. Spend your days by the private pool, with a sun deck overlooking the views. Three bedrooms, two bathrooms — ideal for families, couples, or friends. Tuscany's best wine estates, hilltowns, and thermal spas are all within reach. We're happy to share our favorite local spots.

Location · Family · Comfort

18th-century farmhouse in Cortona, garden, and 4 bathrooms

5 minutes from Cortona, a tastefully restored 18th-century stone farmhouse: frescoes, beams, and original terracotta, surrounded by sunflowers and cypresses. Private garden and great silence, with all the modern comforts. Up to 7 guests, 4 bathrooms, air conditioning in every room, and utilities always included. The ideal base for experiencing Tuscany at a leisurely pace, in total privacy.

Family · Location · Wifi

Tuscan Villa with Pool & Views in Cortona

Set in the peaceful countryside near Cortona, Villa Il Forno offers bright, relaxed Tuscan living with private pool and fenced garden. The 3-bedroom villa hosts up to 6+2 guests and features air conditioning, Wi-Fi, outdoor kitchen, pizza oven and BBQ. Perfect for families and pet-friendly stays, it combines comfort, privacy and authentic charm just minutes from historic villages.

Value · Family · Air conditioning