Holiday rentals with a pool in Castiglione del Lago

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 · Family · Breakfast

Wine Experience Villa in Montepulciano

🏡 Villa Talosa is immersed in the vineyards of the Fattoria della Talosa, a historic winery in Montepulciano that produces Vino Nobile. An authentic place, ideal for relaxing with the magic of the Tuscan countryside and an enchanting view from every window. Just 1.5 km from the historic center, which can also be reached on foot, you can visit our Historic Winery from the 1500s under Piazza Grande: a unique experience between history and passion for wine. Heating and air conditioning are included.

Family · Location · Accuracy

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Location · Value · Kitchen

Separate room, between Cortona and Montepulciano

We are a small farm with a family-run farm on the border between Tuscany and Umbria. The old farmhouse in which we live with our children are surrounded by vineyards and olive groves with a splendid view of Montepulciano. We can sleep in 2 apartments and / or 1 independent room furnished with poor art and originality. In the large garden, available to all, there are two pools (one for children), games, organic vegetable garden. We have a restaurant Pierpaolo cooking the typical Tuscan dishes.

Location · Value · Decor

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.

Family · Location · Getting around

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 · Value · Check-in

2 room apartments in farmhouse whit pool

We have 4 apartments of this type on first floor and on two levels with two bedrooms (one double and a single bedroom. The single bedroom is in the attic and has no door it overlooks the living room), living room with kitchenette, bathroom with shower. The farmhouse enjoys a 360° view of the Umbrian and Tuscan hills and has a garden and shared swimming pool in summer, lounge and playground. This typology can NOT be booked with CHILDREN UNDER 12 or babies and is for max 3 people.

Family · Value · Checkout

La vite - spacious beautiful and comfortable apartment

Finely decorated independent apartment in an old farmhouse in the countryside, large living area with kitchen, two bedrooms each with private bathroom, small balcony at the entrance of the apartment and large veranda of 30sqm available. Ideal situation for those who want to spend time together in contact with nature and a stone's throw from the most beautiful places between Umbria and Tuscany. It is possible to rent it even for only 2 people at a reduced price, ask for info.

Location · Family · Barbecue

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.

Family · Location · Pool

Farmhouse close to Montepulciano

Farmhouse Santa Margherita is a splendidly restored 18th century house that sits on a hilltop on the Tuscan-Umbrian border in sight of Montepulciano. The farmhouse has been recently renovated in order to offer to its guests four vacation apartments. The rooms are very spacious and comfortable. The furnishings are luxurious and include wooden furniture, wrought iron beds and elegant lamps. The kitchens are well equipped so that all your culinary skills can be exercised.

Family · Value · Kitchen

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.

Family · Location · Bathroom

Cottage surrounded by nature

"IL PODERACCIO" is a typical stone farmhouse located on the hills surrounding Lake Trasimeno, immersed in beautiful Mediterranean vegetation. The building is spread across two floors. The pool and garden frame the whole. The swimming pool is open from May 1st to October 15th. Please note that following the COVID 19 emergency, all the directives required by the legislation have been adopted for cleaning and sanitizing the house.

Location · Value · Outdoor spaces