Vacation rentals in Montaleo

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Top-rated vacation rentals in Montaleo

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Top guest favorite

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 in Noce

5 out of 5 average rating, 264 reviews

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.

Superhost

A historic stone tower stands prominently against a clear blue sky, showcasing its weathered facade and narrow windows. The structure's rugged texture and architectural details highlight its ancient origins, set among surrounding buildings and a cobblestone pathway.

Tower in Bibbona

5 out of 5 average rating, 3 reviews

"Templar Tower of 1100"

Discover the "Rocca di Bibbona", the ancient home of the Templars of the 1100s. From its windows, the view is breathtakingly overlooking the Tuscan archipelago: Elba,Capraia, Gorgona. The sunset tinges the sky with shades of the color of fire creating the perfect atmosphere for a candlelit toast on its terrace. A unique journey through time in a tower celebrated in all the industry magazines. Located on the Etruscan coast and surrounded by the most famous vineyards in the world such as Sassicaia and Ornellaia

Top guest favorite

The exterior of the elegant open space is showcased, featuring a well-maintained garden and a stone wall. Two lounge chairs are positioned on the terrace, inviting relaxation. Large glass doors provide access to the interior, surrounded by lush greenery and Mediterranean trees.

Cottage in Casale Marittimo

5 out of 5 average rating, 11 reviews

L'Ondiana, centenary olive trees and seaview

Near Casale Marittimo village, framed by typical Tuscan hills, elegant open space on a villa's lower floor immersed in an enchanting terraced olive grove (the upper floor is private but empty during summer). Living room with dining area and kitchenette, sleeping area with double bed and bathroom with shower. Under the shade of centuries-old olive trees or on the swing with a spectacular view of the sea, the timeless and magical environment of L’Ondiana is ideal for silence and nature lovers.

Guest favorite

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, 116 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

Top guest favorite

A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.

Villa in Montecatini Val di Cecina

4.99 out of 5 average rating, 121 reviews

Belforti Tower

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Top guest favorite

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

4.99 out of 5 average rating, 184 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 favorite

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.

Apartment in Montescudaio

4.93 out of 5 average rating, 154 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 favorite

A spacious living area features a large window with elegant curtains, allowing natural light to illuminate the room. A comfortable sofa adorned with a cozy blanket is positioned facing a wooden coffee table, while a television and decorative elements add to the ambiance.

Condo in San Gimignano

4.93 out of 5 average rating, 123 reviews

Luxury Medieval Tower - Penthouse

Step into the past... San Gimignano Luxury Medieval Tower is right in the heart of the UNESCO town. You will be caught by the sight of San Gimignano's beautiful landscapes and at the same time you will be able to enjoy the luxury amenities of in-town living: walk downstairs to the cafes, bread shop, butcher, restaurants and local shops. Hear the church bells directly from your windows. Walking distance to all of San Gimignano main attractions.

Guest favorite

A charming agriturismo property is seen surrounded by greenery, featuring a light-colored exterior and green shutters. A covered porch offers shaded outdoor space, while colorful flowerbeds enhance the landscape. Nearby, a gravel path leads through the countryside, creating a tranquil rural setting.

Farm stay in Casale Marittimo

4.89 out of 5 average rating, 9 reviews

Valle Incantata Farm and Lab Agritourism

Room with independent access in a family-run farmhouse, all built with wood, clay and recycled material. Ideal location for a relaxing stay in the Tuscan hills, a few kilometers from seaside resorts such as Marina di Cecina, Castagneto Carducci and Bibbona. The room has a private garden with a kitchen, overlooking the farm's natural biolake. Guests can enjoy the lake solarium and precious contact with farm animals.

Guest favorite

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 in Simignano

4.9 out of 5 average rating, 211 reviews

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!

Top guest favorite

An infinity pool reflects the sky, surrounded by olive trees and well-manicured gardens. Comfortable lounge chairs are placed neatly along the pool deck under shaded umbrellas. A gradual elevation creates a seamless transition between the pool area and scenic countryside views.

Farm stay in Palaia

4.98 out of 5 average rating, 171 reviews

Countryside Dream farm in Tuscany

Great place in the middle of Tuscan Hills, you will be surrounded 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.

Guest favorite

The spacious kitchen and living area feature a comfortable sectional sofa, a dining table surrounded by five chairs, and modern appliances. Bright pendant lights hang from the ceiling, and textured tile flooring adds warmth to the space. An open staircase is visible in the background.

Apartment in Montescudaio

5 out of 5 average rating, 24 reviews

Residenza Le Mura

Recently restored apartment of medieval origin in the town's historic village. Large kitchen with 55" TV and elegant sofa, 1 double bedroom, 1 bathroom with shower and washing machine. Balcony overlooking the village square. Air conditioning in all rooms. Free internet access with fiber optics