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Holiday rentals in Montescudaio

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Top-rated holiday rentals in Montescudaio

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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 in Noce
5 out of 5 average rating, 308 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.

Top guest favourite
Flat in Montescudaio
4.82 out of 5 average rating, 127 reviews

Casetta Sole with view over Tuscany Hills and Sea

Cozy rustic-Tuscan apartment in Montescudaio, Etruscan Coast. Carved from an ancient family winery cellar: cool in summer and warm in winter thanks to thick stone walls. Hilly location with stunning views over Tuscan countryside, olive groves, valley, and sea (15 min to beaches). Equipped kitchen, living room with sofa bed, double bedroom, shower bathroom. Private garden with table and sun loungers. Fast WiFi, AC, private parking. Ideal for couples or 3 people seeking authentic relaxation.

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 in Peccioli
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,

Superhost
A vibrant display of flowering white blooms cascades over a rustic stone wall, framing a red wooden fence marked with the name of the property. The scene is accented by the warm sunlight filtering through the greenery, enhancing the inviting entrance.
Apartment in Montescudaio
4.88 out of 5 average rating, 8 reviews

The "Tana del Riccio"

Located in a monastery from the 1700s, just a few steps from the delightful medieval village of Montescudaio, the "Tana del riccio" is a small nest immersed in the peace and greenery of the Tuscan countryside. Conceived as a place of retreat and "good rest" here you can enjoy that silence. In this place, you will not find anything that could represent a distraction from the most beautiful things that nature can offer: no internet, television, no connection other than that with yourself.

Guest favourite
A charming stone cottage is surrounded by lush greenery and tall trees. Two white lounge chairs are positioned on the manicured lawn, accompanied by a small round table. A sun umbrella offers shade, while large windows reflect natural light, showcasing the inviting interior.
Home in Montescudaio
4.96 out of 5 average rating, 123 reviews

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

Guest favourite
A spacious glass-enclosed veranda provides views of the garden and surrounding countryside. The wooden ceiling features exposed beams, complemented by black seating and a glass table. Potted plants add a natural touch, enhancing the tranquil atmosphere of the space.
Farm stay in Montescudaio
4.72 out of 5 average rating, 90 reviews

Countryside apartment in villa close to the beach

Montescudaio, one of the most beautiful villages in Italy and located in the Val di Cecina, is the setting for the Agriturismo Il Polveraio, located in the open countryside and in the middle of an olive grove, with a view of the nearby Tyrrhenian Sea and the Tuscan Archipelago. The agriturismo offers various accommodations located in the main house, dating back to the 11th century AD, and in two outbuildings and will allow you to experience a stay in total peace and tranquillity.

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 in Gambassi Terme
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.

Top guest favourite
An outdoor seating area is showcased on a sunlit terrace, featuring a small wooden table surrounded by colorful chairs. A terracotta pot filled with vibrant red flowers adds a touch of color against the rustic stone wall of the structure.
Home in Casale Marittimo
5 out of 5 average rating, 45 reviews

Countryside-panoramic sea Casale Marittimo Tuscany

Small apartment immersed in the tranquility of the Tuscan countryside. Ten minutes from the Etruscan Coast. Sea view. For a stay full of privacy and relaxation, but with all the attractions of the area just a stone's throw away. Your furry friend is welcome, ONLY ONE and of SMALL size. From here, there are many hiking trails and bike paths to discover the suggestive landscapes. Excellent typical restaurants, and wineries!!! Enjoy your stay! Accommodation tax to be paid on site

Top guest favourite
A modern kitchen and dining area feature sleek cabinetry and a spacious dining table. White chairs surround the table, complemented by a vase of flowers. Large windows enhance the room's brightness, while neutral-colored tiles create a clean and inviting atmosphere.
Flat in Montescudaio
4.93 out of 5 average rating, 165 reviews

Elegant and bright apartment in Montescudaio

The apartment has been recently renovated, very bright and welcoming, the furnishings are modern and practically new. Located in the residential area of Montescudaio, quiet and peaceful from where you can easily reach the most characteristic places of Tuscany: medieval villages, enchanting hills and all the splendid historic cities (Pisa, Florence, Siena...) that make Tuscany such a popular destination. Just 20 minutes to the sea. Your vacation will be unforgettable!

Guest favourite
A white umbrella provides shade over a small round table, which holds a potted cactus. In the background, rolling hills and olive trees are visible, accompanied by a swimming pool reflecting the sky. Lush greenery surrounds the area, enhancing the peaceful countryside ambiance.
Guest suite in Casale Marittimo
4.83 out of 5 average rating, 110 reviews

The cypress

Dependance of 30 sqm new building located in the context of property with independent main house immersed in the beautiful Tuscan countryside 12 km from the sea and close to centers of cultural interest. The beautiful villages of Bolgheri and Castagneto Carducci are within easy reach. A half-hour drive from Volterra. The furnishings are completely new. Garden and swimming pool with sea view available for guests.

Top guest favourite
A sunlit terrace features a wooden dining table with chairs, surrounded by vibrant red flowers in pots. An awning provides shade, and a view of nearby buildings is visible. The tiled flooring adds to the rustic charm of this outdoor space.
Home in Castello
4.94 out of 5 average rating, 36 reviews

Da 7 Cervelli

The XIXth century house is in a small village in Tuscany, 10 km to the Tyrrhenian Sea, 25km to Volterra, 20 km to Bolgheri, 80 km to Siena and 100 km to Florence. The train station (Cecina) it's 9km away. Slow life, excellent wine and food, historical heritage, this part of Tuscany it's a great choice for your holidays. For your stay you can find a private parking and a beautyful country garden.

Guest favourite
Flat in Montescudaio
4.92 out of 5 average rating, 79 reviews

The Borgo Suite

Comfortable and charming two-room apartment, newly renovated, located in the heart of the historic center of Montescudaio. The Suite has the use of a large terrace that offers a breathtaking view from the hills to the sea overlooking the islands of the Tuscan archipelago. Strategically located both for enjoying a beach vacation and for relaxing in the tranquility of a medieval village

Popular amenities for Montescudaio holiday rentals

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