
Holiday rentals in Casole d'Elsa
Find and book unique accommodation on Airbnb
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 €60 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 & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
10 of Casole d'Elsa holiday rentals include wifi 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.

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, and 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, with relaxation in the hot tub and al fresco dinners. A memorable getaway awaits you in this little 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' walk away, loading and unloading allowed. National Identification Code: IT052004C2R23DIUHK

Holiday House "Anna" - the MUSICIAN for 4-5 persons
“The MUSICIAN” It is located in the historic center, within a 1400's home It is close to 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,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.

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.

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.

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.

Romantic Villa with private pool - "Il Pollaio"
Il Pollaio is a traditional, charming Tuscan stone house with a warm, relaxed atmosphere, surrounded by the peace and quiet of the countryside. With air conditioning, a private pool nestled in the greenery and a fully fenced property. Extra services on request: private chef and housekeeping every other day. Ideally located, yet secluded and private. Ample parking. PLEASE NOTE: Read the details under “Show more” in “Other things to note”

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.
Popular amenities for Casole d'Elsa holiday rentals
Other great holiday rentals in Casole d'Elsa

Exclusive Tuscan Villa with private pool

TuscanView 360: 3 bedr, 2 baths, free parking

Luxury Medieval Tower - Penthouse

Donna Lisa - Cantona Estate

Private Tuscan villa with pool steps from village

Il Cristallo – Dream Getaway in Tuscany

Orli "Home & Relax" holiday home

Luxury Residence in the Heart of San Gimignano
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!
Destinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Cala Violina
- Stazione Santa Maria Novella
- Mugello Circuit
- Parco Regionale Della Maremma
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





