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Holiday rentals in Montecastello

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Top-rated holiday rentals in Montecastello

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A well-furnished room features a comfortable chair next to a wooden armoire and a TV mounted on the wall. Soft lighting is provided by a standing lamp, while textured walls and wood-beamed ceilings enhance the warm atmosphere. Natural light filters through the window drapes.
Apartment
4.97 out of 5 average rating, 130 reviews

La Rocca Tourist Rental

In the beautiful medieval village, nestled in the heart of Tuscany, bedroom, bathroom and living room with table in typical Tuscan style. Equipped with a terrace with panoramic views. It is located in the town center and close to bars/restaurants and other shops. Free parking. The train station is 5 km away. A few kilometers from the FI-PI-LI. Located in a favorable position to visit all of Tuscany, the distances are: Florence at 51 km, Pisa at 37 km, Lucca at 45 km, San Gimignano at 45 km and Livorno at 46 km.

Top guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Apartment
5 out of 5 average rating, 306 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Guest favourite
An inviting outdoor space is presented, featuring a clear pool reflecting the evening sky. Comfortable lounge chairs are arranged nearby on the well-maintained lawn, surrounded by potted plants. The scenic hillside view in the background adds to the serene atmosphere.
Apartment
4.96 out of 5 average rating, 142 reviews

Casa Luna-Splendida overlooking the pool and Tuscan nature

My husband and I fell in love at first sight with this beautiful place. So we have moved here our whole life. Ideally located on the hill of Morrona,this landscape affords unique views over the hills near Pisa,put us in direct contact with a calm nature and gives us a wonderful spectacle of the fascinating and surprising course of seasons. The location is enhanced by the swimming pool with hydromassage,for those seeking a moment that will remain on their skin and in their hearts for a long time

Top guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home
4.98 out of 5 average rating, 220 reviews

The Chianti Classico Sunset

Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Top guest favourite
A spacious terrace is surrounded by lush greenery, featuring terracotta pots filled with plants. Comfortable wooden chairs are positioned to invite relaxation, overlooking scenic hills in the distance. A soft canopy provides shade, enhancing the tranquil atmosphere of this outdoor space.
Home
4.99 out of 5 average rating, 134 reviews

House with a breathless view in Tuscany

Halfway between Pisa and Florence this house comes with a large panoramic terrace, equipped with sunchairs and a large table for outdoor dining. Below, an hanging garden on the property overlooks one of the most striking views in Tuscany. The location is strategic, in the beating heart of an ancient medieval village, now home to an open-air contemporary art museum. Peccioli is a great starting point for those who want to visit the art cities of Tuscany, or immerse yourself in local life,

Top guest favourite
Home
4.95 out of 5 average rating, 220 reviews

al castello dell montacchita stunning view

N. REGISTRAZIONE 50024LTN0077 Cottage unico e romantico con un'atmosfera magica e vista mozzafiato sulla valle, con grande giardino ed accesso privato, ristrutturato in stile rustico all'interno di un'antica rocca medievale. Luogo unico, ottimo punto di partenza per visitare Pisa, Lucca, Firenze San Gimignano e a soli 40 minuti dal mare e situata nella zona del tartufo. Ricorda prima di prenotare: coloro che non sono nominati nella prenotazione non potranno entrare nella proprietà.

Top guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home
5 out of 5 average rating, 204 reviews

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.

Guest favourite
A bright living area features a light-colored sofa adorned with decorative cushions in various patterns. A large window allows natural light to fill the space, enhancing the wooden ceiling beams. A television is positioned across from the sofa, contributing to the room's inviting layout.
Apartment
4.87 out of 5 average rating, 145 reviews

Lovely apartment in the center of Pontedera

Enjoy easy access to everything from this perfectly located home base. The apartment is furnished with care, with exposed beams and bricks, equipped with a kitchen equipped with a microwave oven and coffee maker. Bathroom with shower. Downtown and train station within walking distance. Pontedera is in a strategic location just minutes from the Tuscan hills, 20 minutes from the sea and Pisa, 20 minutes from Lucca and 40 minutes from Florence

Top guest favourite
An independent building is surrounded by lush greenery, featuring blue shutters and a terracotta patio area. Small tables are set for outdoor seating. The expansive garden includes mature trees and various plants, creating a serene outdoor environment.
Flat
4.96 out of 5 average rating, 124 reviews

Podere Le Murella "Sunset"

A cozy retreat for two, set among the green Tuscan hills. Enjoy a private patio for outdoor dining, large garden, free Wi-Fi, fully equipped kitchen, coffee machine, washing machine, dryer, barbecue area, and linens included. Private parking. Ideal for a romantic escape or relaxing stay near Pisa, Florence, Volterra, and charming villages. A perfect base to explore nature, art, and local life—all year round.

Top guest favourite
A spacious living area features exposed wooden beams and warm, neutral tones. Comfortable seating is arranged around a light coffee table, with decor including a magazine and a small centerpiece. A fully equipped kitchen is visible in the background, complemented by natural light from nearby windows.
Flat in Peccioli
4.89 out of 5 average rating, 117 reviews

Da Vinci: entire space in the heart of Tuscany

Come and take a vacation at our beautiful apartment at Peccioli, Tuscany! Enjoy a renovated space, with A/C in the center if a medieval town next to bars, restaurants and shops. Beautifully decorated, with new appliances and furniture, high-speed internet, and all you need to enjoy your time in Italy. Peccioli is a gem in the heart of Tuscany, near all the big cities and touristic attractions.

Top guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay
4.91 out of 5 average rating, 242 reviews

Casa al Gianni - Hut

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Top guest favourite
The image features a serene infinity pool reflecting the surrounding trees and villa during sunset. Sun loungers are positioned beside the pool, and the well-maintained outdoor area offers a tranquil ambiance enhanced by the natural landscape.
Farm stay
4.99 out of 5 average rating, 316 reviews

Tenuta Chiudendone in Tuscany

Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Popular amenities for Montecastello holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Pisa
  5. Montecastello