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Holiday houses in Casole d'Elsa

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Top-rated holiday rentals in Casole d'Elsa

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Top Guest favourite
An open-plan living area is shown, featuring warm, rustic décor with exposed wooden beams and terracotta flooring. A dining table for six is visible, alongside comfortable seating arrangements. The kitchen area, equipped with modern amenities, is integrated into the space, providing a welcoming atmosphere.
Apartment in Casole d'Elsa
5 out of 5 average rating, 35 reviews

Holiday House "Anna" - the MUSICIAN for 4-5 persons

"the MUSICIAN" IS located IN the historic center, inside a house from 1400 IS near Siena, Florence, San Gimignano, Volterra, and the Chianti area. Suitable for those who love the countryside, but want the advantages offered by a country with all the services: shops,restaurants,bars,post office,bank,pharmacy,church, tourist office, museum. Live the summer experience of a country that alternates its tranquility with moments animated by parties,markets,music and the tradition of the Palio (on the 2nd Sunday of July).

Top Guest favourite
Aerial view showcases the rustic property nestled among the lush vineyards. Sunlight casts a warm glow over the hills, while a sparkling pool is situated near the residences, surrounded by greenery. The tranquil landscape includes gently rolling hills and rows of grapevines.
Condo in Noce
5 out of 5 average rating, 307 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
A large window with white curtains frames a breathtaking view of rolling green hills under a blue sky. A tall cypress tree is visible in the foreground, adding to the serene landscape that extends towards distant mountains.
Condo in Casole d'Elsa
4.92 out of 5 average rating, 13 reviews

Dimora San Donato - Apt.1985

Dimora San Donato, located in the historic centre of Casole d'Elsa, combines refinement and elegance. The interiors, spacious with great attention to detail, offer a perfect blend between tradition and modernity. The location allows guests to immerse themselves in the daily life of the village, surrounded by a breathtaking landscape of rolling hills and centuries old cypresses. The Dimora represents a journey into the heart of Tuscany, where history, culture and natural beauty come together.

Top Guest favourite
A panoramic view of a swimming pool is presented, surrounded by green umbrellas and lounge chairs. Rolling hills and lush greenery create a serene backdrop, enhancing the tranquil atmosphere. The clear blue water reflects the sky, inviting relaxation in a peaceful outdoor setting.
Cottage in Casole d'Elsa
4.93 out of 5 average rating, 29 reviews

Cottage with patio,1 km walk to the local village

✅ 45 m² on ground floor with kitchen ,1 double bedroom ,1 bedroom with 2 twin beds both with airco, 1 bathroom. Large patio with shade ideal for morning coffee and all your meals. ✅ Panoramic pool, ideal for relaxtion and family fun ✅ 1 km easy walking to the medieval town with cobblestone streets and delightful details at every corner ✅ Central location to visit hidden gems + many Unesco Heritage Sites Leccio Cottage is part of Monti 1824 farm,composed of 6 accommodations + pool

Top Guest favourite
A charming street in the historical center is lined with rustic brick buildings. Potted plants and flowers adorn the facades, while the pathway features a mix of smooth stone and tile. Overhead, the sky is partially cloudy, allowing natural light to illuminate the scene.
Apartment in Casole d'Elsa
4.96 out of 5 average rating, 27 reviews

Mirella apartment in the historic center

Comodo appartamento per 2-4 persone, in centro storico a Casole d’Elsa, con vista panoramica dalla terrazza sulle colline toscane. A 18 km da San Gimignano, 25 km da Volterra e 35 km da Siena. L’alloggio offre due camere, una matrimoniale e una doppia con letti singoli, bagno con doccia, sala da pranzo con divano e tv, cucina, terrazza, cantina, Wi-Fi, stanzino esterno con lavatrice. Parcheggio gratuito a 2 e 5 minuti a piedi, concesso il carico e scarico. CIN: IT052004C2R23DIUHK

Top Guest favourite
A serene outdoor pool area is framed by lush green grass, featuring several sun loungers and umbrellas. The clear water in the pool reflects the blue sky, while tall cypress trees provide a natural backdrop to the tranquil setting.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 447 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Top Guest favourite
Loft in Radicondoli
4.97 out of 5 average rating, 118 reviews

Il Frantoio - Charming Loft in the old town

This elegant and spacious Loft “Il Frantoio”, with a living area of 160 m², is located in the old town of the medieval village Radicondoli. The open space kitchen and livingroom area is designed to give a high comfort and reminds us the ancient function of this bluilding that was the oil mill of the comunity. The Loft was recently completly restored with a high focus on comfort and best quality materials.

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 in Simignano
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!

Guest favourite
A refreshing swimming pool is surrounded by lush greenery and sun loungers. Colorful umbrellas provide shade, enhancing the outdoor relaxation area. In the background, the rustic stone farmhouse is visible among the trees, complementing the tranquil setting.
Apartment in Casole D'Elsa
4.94 out of 5 average rating, 111 reviews

Girasoli apartment with pool in farmhouse

Going up 17 steps you will be hosted in an apartment located on the second floor with a separate entrance. Consisting of a kitchen, bathroom with shower and double bedroom with 2 windows overlooking the village of Casole d'Elsa and the swimming pool. Mosquito nets on the windows. Small terrace shared with the Manuela apartment TO BE PAID - ACCOMMODATION TAX €1 per person

Guest favourite
Cottage in San Gimignano
4.84 out of 5 average rating, 235 reviews

Countryside Cottage With View - Le Rondini apt

The cottage is part of a charming traditional Tuscan farmhouse, built in stone and situated in one of the most beautiful areas of Tuscany.A lovely garden surrounds the house and has magnificent views of the medieval town with its famous towers.

Top Guest favourite
The exterior of a rustic stone building is showcased, featuring traditional wooden shutters and a charming door. Potted plants and climbing vines adorn the entrance, while a small outdoor seating area with a table and chairs is visible on the green lawn.
Farm stay in Siena
4.97 out of 5 average rating, 305 reviews

Authentic Tuscan Country House WITH A/C

L'appartamento "Pergola" (75 mq), è una delle due unità abitative indipendenti che compongono l'agriturismo Terra Rossa, situato nel cuore della campagna senese a pochissimi minuti di macchina dal centro storico.

Top Guest favourite
Apartment in Siena
4.99 out of 5 average rating, 412 reviews

Diacceto19 Siena Apartments Int.1

One of the two class apartment ( Int.1-Int.2 ) in the heart of Siena, furnished with great care, and equipped with every comfort, with one of the most beautiful and photographed view of the city.

Popular amenities for Casole d'Elsa holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Casole d'Elsa