House holiday rentals in Montescudaio

Infinity pool in Chianti 1

Our house is a part of a stone farmhouse completely independent from the rest of the adjacent property. Arranged on three floors, on the ground floor there is a large entrance hall, a large living room with fireplace, a bedroom with 1 double bed and a bathroom with window. On the first floor there are two bedrooms (2 +2 beds) with a bathroom with window. In the basement, at garden level, there is the kitchen and the dining room. From the kitchen you access the outside where you will find an area for outdoor dining with a large dining table under a pergola. You then go down towards the garden with barbecue area.

Value · Family · Pool

Casa al Gianni - The Simignano Barn

Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!

Value · Location · Walkability

Open space surrounded by nature

Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring

Location · Value · Wi-Fi

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Location · Family · Kitchen

Countryside-panoramic sea Casale Marittimo Tuscany

Small apartment immersed in the tranquility of the Tuscan countryside. Ten minutes from the Etruscan Coast. Sea view. To spend a stay in the name of privacy and relaxation, but with all the attractions of the area just a short walk from here. I welcome your furry friend,JUST ONE and SMALL. From here many hiking trails and bike paths start to discover the evocative landscapes. Great typical restaurants, and wineries.!!! Enjoy your stay! Tourist tax is due at check-out.

Location · Family · Kitchen

House with a breathless view in Tuscany

Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

Family · Location · Outdoor spaces

La Casina dei Caci

This house offers, for those who love nature, a landscape that extends from the wooded hills to the sea where we can admire a splendid sunset. For those who love to take walks or go cycling, there are itineraries to follow, rest assured. This accommodation is about 5 km from the center of Montecatini Val di Cecina, of which 3 km of paved road and 2 km of dirt road. From January 1, 2026, an accommodation tax of €1.50 per person per night to be paid on site.

Value · Location · Access

Nada Home

3 comfortable, fully air-conditioned double bedrooms, each with its own private bathroom, in the heart of Chianti, ideally located between Florence, Siena and San Gimignano. A welcoming, well-kept home in the peaceful Tuscan countryside. Fully equipped kitchen with dishwasher, oven and bar area, plus a laundry room with washing machine and dryer. Private garden for your exclusive use with a private hydromassage pool, heated in winter upon request 🌷

Family · Value · Decor

The Cottage to relax and enjoy

Detached country house – for exclusive use – in stone and glass from the 18th century; ideal for 4 people. The spacious wooden terrace at the house with a large dining table invites you to socialize. On the terrace by the saltwater pool (10m x 5m, depth 1.4m-2.4m), you can relax on the sun loungers and deckchairs. Large property with olive and fruit trees, completely self-sufficient accommodation thanks to photovoltaics. (CIN IT050012C29N4AT4OD)

Location · Value · Amenities

Lovely house in a scenic and paiceful location

This beautiful house is nestled in a quiet and panoramic location, making it the perfect spot to get away from it all. With three bedrooms, three bathrooms, and room for up to six guests, this is the perfect place for a group of friends or a large family to call home while exploring Tuscany. Spend your days hiking the picturesque landscape, wandering through charming villages, or simply relaxing in the lovely gardens of the house.

Location · Value · Checkout

Frontemare house with exclusive sea access

Casa Frontemare is a completely renovated property with direct access to the sea, from which you can enjoy a panoramic view of the sea, the Tuscan islands and wonderful sunsets. It is a perfect place for those who love a relaxing and private vacation. The proximity to the Tuscan art cities and the small typical villages means that it is also possible to discover new places and discover the flavors of Italian cuisine.

Family · Location · Nearby

Cercis - La Palmierina

The apartment is part of a completely fenced estate of 60 hectares of unspoiled nature: more than 1000 olive trees, countless cypresses and fragrant forests create an idyllic environment for those seeking tranquility and silence. The Palmierina estate is near Castelfalfi (a true jewel of medieval architecture) and close to Florence (50 Km), Siena (50 Km), and Pisa (50 Km). There are two golf courses nearby.

Value · Location · Condition