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Holiday houses in Casole d'Elsa

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Quick stats about holiday rentals in Casole d'Elsa

  • Total holiday rentals

    Explore 10 holiday rentals in Casole d'Elsa

  • Nightly prices starting at

    Casole d'Elsa holiday rentals start at $98 AUD per night before taxes and fees

  • Verified guest reviews

    Over 390 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Casole d'Elsa holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Casole d'Elsa rentals

  • 5 Average rating

    Casole d'Elsa stays are highly rated by guests—averaging 5 out of 5!

Top-rated holiday rentals in Casole d'Elsa

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

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Guest favourite
A spacious living area features a large wooden table set for a meal, adorned with fresh fruits and glassware. A comfortable red couch is positioned nearby, complemented by framed black and white photographs on the wall and stylish pendant lights above.
Condo in Casole d'Elsa
4.93 out of 5 average rating, 194 reviews

La Casetta

“La Casetta”, is a new restored enchanting apartment immersed in the splendid Tuscan countryside, only 2 kms from the medieval village of Casole d'Elsa in Siena province. Situated in a old farm complex with private entrance, large private garden, and access to the communal swimming pool. Furnished with utmost care down to the finest detail. Ideal for a relaxing, regenerative week with family or friends, emerged in an uncontaminated natural landscape. Possibility of excursions on foot and by bicycle in an evocative natural setting of lush forests and gentle hills of rare beauty. One can enjoy local dishes of the wonderful Tuscan tradition in many of the nearby restaurants or organize splendid home-cooked meals with the barbecue in the garden. Ideally situated for visits the many nearby towns and cities rich in art and beauty: 30 mins to Siena, 1 hour to Florence ,30 mins to San Gimignano and Volterra, 45 mins to the Chianti area. La Casetta is the ideal place to regenerate your body and mind. (We are the same owners of “La Senesina" apartment near Siena check out our rating on the web! Our 5 stars ratings are your warranty for a great stunning vacation)

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
4.93 out of 5 average rating, 285 reviews

Casa al Gianni - Hut

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to ‘Casa al Gianni’, our farm stay in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds and the companionship of our animals. It’s an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a holiday; it’s a return to our roots. This haven of peace will stay with you in your heart. We look forward to welcoming you!

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
4.97 out of 5 average rating, 33 reviews

Mirella apartment in the historic center

Comfortable apartment for 2-4 people, in the historic center of Casole d 'Elsa, with a panoramic view from the terrace on the Tuscan hills. 18 km from San Gimignano, 25 km from Volterra and 35 km from Siena. The accommodation offers two bedrooms, a double and a double with single beds, bathroom with shower, dining room with sofa and TV, kitchen, terrace, cellar, Wi-Fi, outdoor room with washing machine. Free parking 2 and 5 minutes on foot, loading and unloading allowed. National Identification Code: IT052004C2R23DIUHK

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
5.0 out of 5 average rating, 37 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).

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 138 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top Guest favourite
A welcoming entrance features a stone wall adorned with vibrant flower pots. A spacious patio leads to the home, complemented by a wooden bench and a picturesque natural landscape in the background, showcasing rolling hills under a clear sky.
Home in Casole d'Elsa
4.99 out of 5 average rating, 111 reviews

Casa Panorama

Welcome to Casa Panorama! A cozy apartment situated in the wonderful Tuscan countryside just a stone's throw away from the medieval town of Casole d'Elsa.Casa Panorama is in between some of the most beautiful locations such as Siena,Monteriggioni,Florence,San Gimignan,Volterra and many other hidden hilltop Tuscan jewels.Our house is situated less than 1 km from the center of the very romantic town of Casole d'Elsa where there are restaurants and much to see as far as culture and art is concerned

Guest favourite
An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.
Holiday home in Sovicille
4.97 out of 5 average rating, 160 reviews

Podere La Castellina - No. 1 COTTAGE

Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Guest favourite
Condo in Casole d'Elsa
4.95 out of 5 average rating, 20 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.

Superhost
The stone villa is framed by lush greenery, showcasing a rustic façade and a large arched window. The surrounding manicured lawn and trees create a serene ambiance, with distant hills hinting at the scenic views offered by the property.
Cottage in Casole d'Elsa
4.9 out of 5 average rating, 20 reviews

Stone cottage + private garden near San Gimignano

✅ 80 m² on 2 floors. Equipped kitchen ,1 double bedroom and 1 bedroom with 2 twin beds both with airco, 2 full bathrooms. Patio ideal for morning coffee and relaxing evenings under the stars ✨✨ ✅ Unique panoramic views from the pool ✅ 1 km easy walking to the medieval town Casole with cobblestone streets and delightful restaurants ✅ Perfect central location to visit hidden gems + Unesco Heritage Sites Noce Cottage is part of Monti 1824 farmhouse ,composed of 6 accommodations + pool

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.
Condo in Noce
5.0 out of 5 average rating, 349 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is a family-run property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can organise a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.

Guest favourite
A sunlit pool area features a clear, inviting swimming pool surrounded by green lawn. Bright umbrellas and lounge chairs are arranged near the pool, providing shaded seating. Lush greenery and a stone wall create a cozy, secluded atmosphere.
Apartment in Casole d'Elsa
4.94 out of 5 average rating, 114 reviews

Girasoli apartment with pool in farmhouse

Going up 17 steps you will be hosted in an apartment located on the first floor with an independent entrance. Composed of kitchen, bathroom with shower and double bedroom with 2 windows overlooking the village of Casole d 'Elsa and the pool. Screen screens on the windows. Small terrace shared with the Manuela apartment IT IS MANDATORY TO PAY ACCOMMODATION TAX AT CHECK-IN €1 per person in cash Use of heating from 1 November to 15 April (regional law) €15.00 per day.

Top Guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 104 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Popular amenities for Casole d'Elsa holiday rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Casole d''Elsa?

    Casole d''Elsa has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Casole d''Elsa?

    Four-legged friends are welcome in Casole d''Elsa. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Casole d''Elsa?

    Yes! Work meets play with ease at over 10 vacation rentals in Casole d''Elsa featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Casole d''Elsa vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Casole d''Elsa, available on Airbnb. Make a splash and soak up the sun in style!