
Holiday houses in Casole d'Elsa
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Top-rated holiday rentals in Casole d'Elsa
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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.

The Chianti Classico Sunset
Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Farmhouse with pool in Chianti
Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is on the first floor of the main farmhouse, with independent access and garden with trees. The rustic furnishings in the classic Tuscan style, with wooden beam ceilings and terracotta floors give a characteristic touch to the environment.

Your Tuscan oak tree house, enchanting Val d'Orcia
The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Casa degli Allegri
Open the large glass doors to let the scent of Tuscan herbs in; step onto the terrace and uncork a Sangiovese wine to soak in the stunning views of the Duomo. Nestled on the roofs of the authentic Santa Croce and Sant'Ambrogio neighborhoods, this romantic rooftop flat features brand-new appliances, antique and handcrafted furniture, two bathrooms, and all the amenities you need for the perfect base to explore Firenze.

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.

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!

Girasoli apartment with pool in farmhouse
Going up 17 steps, you will be accommodated 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. Shared terrace with the Manuela apartment TO BE PAID - TOURIST TAX 1€ per person

Suite in Castello di Valle
A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.

Panoramic loft with terrace near Ponte Vecchio
Luminoso e silenzioso loft all'ultimo piano nel quartiere Oltrarno del centro storico. Vicino a tutti i monumenti e trasporti pubblici. Offre tutti i comfort per un soggiorno rilassante. Splendida vista su Palazzo Pitti e sui giardini di Boboli. Nessun ascensore. Per 1-2 persone.

Casale Santa Barbara - Exclusive Apartment
Your private Tuscan retreat between Pienza and Montepulciano. A spacious 100 m² apartment for two, with exclusive access, a large private garden and breathtaking views over the Val d’Orcia hills. Elegance, calm and authenticity — just you… and Tuscany.

Stunning Tuscan apartment for 2
This apartment - tucked away privately and enjoying a stunning view from its terrace - is part of an 'agriturismo' farm which produces organic Chianti Classico. Spacious and light, it has 1 double bedroom, 1 sitting room, 1 bathroom and a kitchen.
Popular amenities for Casole d'Elsa holiday rentals
Other great holiday rentals in Casole d'Elsa

AnticaVista, Luxury Apartment with Tower Views

House "Il Campanile"

Romantic Tuscan Holiday House

Farmhouse with private pool Vacavilla Exclusive

Romantic Villa with private pool - "Il Pollaio"

Radicondoli House

Rustic Tuscan with swimming pool

Herons Superior Apartment - Splendid view!
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 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!
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.
Destinations to explore
- Santa Maria Novella
- Piazza della Signoria
- Mercato Centrale
- Ponte Vecchio
- Santa Maria Novella
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Salvatore Ferragamo Museum
- Cathedral of Santa Maria del Fiore
- Marina di Cecina
- Del Chianti
- Siena Cathedral
- Porta Elisa
- Basilica of Santa Maria Novella
- Spiagge Bianche
- Piazza dei Cavalieri
- Cala Violina
- Piazza del Duomo (Pisa)
- Uffizi Gallery
- Piazzale Michelangelo
- Fortezza da Basso
- Piazza della Repubblica
- Gulf of Baratti
- Pitti Palace




