Vacation rentals in Casole d'Elsa

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)

Casa al Gianni - The Simignano Barn

Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

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 away on foot, loading and unloading allowed. National Identification Code: IT052004C2R23DIUHK

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).

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

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.

Manuela apartment with pool in farmhouse

You will be staying in an apartment located on the second floor, with a separate entrance, which is accessed by climbing 17 steps. It consists of a kitchen, two bedrooms (one double and one with 2 single beds), a bathroom with a shower, and mosquito nets on the windows. Small balcony shared with the GIRASOLI apartment. IT IS MANDATORY TO PAY THE ACCOMMODATION TAX AT CHECK-IN: €1 per person for the first 5 days. Heating is allowed from November 1 to April 15 (Regional Law) at €20.00 per day

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

Tuscan Rustic with Pool

Rustic cottage overlooking a typical Sienese farmyard. It is on the ground floor and consists of a kitchen-living room, a bathroom and a bedroom overlooking the green Tuscan hills. It has a large garden and swimming pool. The Cottage is for exclusive use. The area is very quiet and ideal for relaxing vacations. We are in the middle of two significant cities, such as Siena and Florence, but if you want to discover typical villages, a few km away are San Gimignano, Volterra, Monteriggioni.

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.

Florence & Siena • Terrace • Private Parking • A/C

Imagine waking up to sunlight filling the apartment and enjoying breakfast overlooking the Tuscan hills. Bright top-floor apartment with elevator, panoramic terrace and 180° open views, between Florence and Siena, in a quiet private area with no through traffic. Perfect for families, with parking, air conditioning, fast Wi-Fi, fully equipped kitchen and all the comforts to explore Tuscany’s villages, wineries, art cities and iconic landscapes.

Green Dome @ The Land Before Time Retreats

Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.