Vacation rentals in Guardistallo

5 out of 5 average rating, 282 reviews

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.

Condo

Podere Vergianoni immerso nelChianti con piscina

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.

A rustic dining area features a long wooden table set with linens and decorative items. The space is illuminated by a chandelier and has large windows offering views of the surrounding landscape, with a stone fireplace and traditional frescoes adorning the walls.

4.96 out of 5 average rating, 221 reviews

Giglio Blu Charming Loft

The accommodation is a portion of a historical noble residence dating back to the 14th century, adorned with frescoes and tastefully restored. It is located on the ground floor of a quiet and safe street, with a private and independent entrance and self check-in. The space is cozy, comfortable, and elegant, perfect for guests seeking an authentic Tuscan experience with modern comfort and technology. It is situated just a few kilometers away from Florence, Pisa, Lucca, Vinci, San Gimignano...

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.

4.99 out of 5 average rating, 132 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,

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.

4.96 out of 5 average rating, 121 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

4.72 out of 5 average rating, 88 reviews

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

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.

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.

4.99 out of 5 average rating, 195 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.

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.

5 out of 5 average rating, 32 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. To spend a stay in the name 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 SMALL. From here, many hiking trails and bike paths start to discover the evocative landscapes. Excellent typical restaurants and wineries!!! Have a great stay! Accommodation tax to be paid on site

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.

4.93 out of 5 average rating, 161 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!

4.83 out of 5 average rating, 110 reviews

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

The cypress

New building of 30 square meters 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 easily accessible. Half anhour drive from Volterra. The furniture is brand new. Garden and pool with sea view with sea view available for guests to use.

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.

4.94 out of 5 average rating, 36 reviews

From 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.

4.92 out of 5 average rating, 75 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

4.91 out of 5 average rating, 230 reviews

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

Casa al Gianni - Capanna

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!

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Popular amenities for Guardistallo vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Guardistallo

4.5 out of 5 average rating, 4 reviews

[10 min from the sea]Apartment with garden+Jacuzzi

4.5 out of 5 average rating, 4 reviews

Casa Vacanze Melograno

A two-story stone house is surrounded by lush greenery. Tall cypress trees frame the property, while a spacious lawn gently slopes towards the building. Multiple outdoor chairs are positioned on the patio, offering a peaceful setting to enjoy the natural landscape.

5 out of 5 average rating, 55 reviews

Debbio di Chicco

4.92 out of 5 average rating, 13 reviews

A three-story building is depicted, featuring a combination of window shutters in green and decorative flower boxes. The entrance is framed by lush plants, while the exterior walls are painted in a soft, light color, enhancing the building's traditional character.

Condo

Delightful two-room apartment with sea view

A terrace features a table set for two with a scenic view of lush greenery and rolling hills in the distance. Two comfortable, dark wicker chairs are positioned around the table, inviting relaxation. The clear sky enhances the open atmosphere of the space.

5 out of 5 average rating, 3 reviews

Alice's House by Interhome

An outdoor patio area features a large umbrella providing shade over a table surrounded by folding chairs. A seating area with a cozy lounge chair is visible, and a well-maintained garden with greenery surrounds the space, creating a serene atmosphere.

4.94 out of 5 average rating, 17 reviews

IL PICCINO 29, Romantic Experience in the Hamlet....

The image showcases a historic stone facade of a building, highlighted by a large archway. The weathered textures of the walls, with visible bricks and stones, create a sense of age and history. Electric wires are prominently displayed, adding a modern contrast to the ancient architecture.

Condo

5 out of 5 average rating, 4 reviews

In the Castle

A rustic villa constructed of stone stands among lush greenery. Potted white flowers adorn the front area, with steps leading up to the entrance. Tall cypress trees frame the scene, while the building features various windows and a mix of architectural elements.