
Villa holiday rentals in Casentino
Find and book unique villas on Airbnb
Top-rated villa rentals in Casentino
Guests agree: These villas are highly rated for location, cleanliness and more.

The Farmhouse Cottage
Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Poggio del Fattore-Villa with pool, hilltop, Chianti
Poggio del Fattore is situated at the eastern edge of the Chianti region in Valdambra, a green valley that joins the lands of Florence, Siena and Arezzo. The farmstead is on the top of an hill and lies at the end of a long private road through a large olive growing estate; therefore you absolutely need a car. The breathtaking landscapes and the location of the villa offer the privacy needed for a peaceful and relaxing holiday and a perfect departure point from which to explore central Tuscany.

Tuscan charm of villa - countryside
Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

Chianti Villa: Jacuzzi & Wheelchair Accessible
Nestled in Chianti vineyards, close to Florence. 135 sq m house with large kitchen w/ fireplace, 3 bedrooms x tot. 9 beds, 3 bathrooms. An additional bedroom (for an extra fee) to add on request x tot. 11 beds. Ground floor is fully accessible for guests with disabilities, with bedroom, bathroom, and kitchen accessible by wheelchair. The entrance is accessible directly from the private parking lot. Air conditioning is available. Jacuzzi available exclusive use at an additional cost.

San Giovanni in Poggio, villa Meriggio 95mq
Detached house, two double bedrooms, two bathrooms with shower, living room with fully equipped kitchen (dishwasher, washing machine, oven, microwave), double sofa bed, private garden with equipped pergola. Satellite TV and free Wi-Fi. Additional services at the property, upon reservation, include Focus brand Jarifa2 6.7 pedal-assisted bicycles and a wellness area with a Forest outdoor Finnish sauna and a heated mini-pool with hydromassage and chromotherapy with panoramic views.

Tuscan Dream Villa @ Rustic Elegance Near Florence
🌿Welcome to Villa La Conigliera🌿, an ideal retreat for a romantic getaway or a relaxing stay, just a few kilometers from Florence. 🌟Set in the peaceful Tuscan countryside, overlooking an ancient courtyard, it blends rustic charm with modern comfort. Perfect for couples or families with a newborn, with a crib available upon request 👶. Two adjacent villas for 4 and 6 guests complete the hamlet. 🚗 A car/motorbike is recommended for exploring the beautiful surroundings.

Luxury Villa in the very heart of Chianti
The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.

Tuscany View - Villa Arianna
This beautiful villa, which can accommodate up to ten (10) people, will provide an unparalleled Tuscan experience. While positioned perfectly to allow easy access to the most beautiful towns and villages of southern/central Tuscany (such as Arezzo, Florence, Siena, Cortona, Montepulciano) and northern Umbria (such as Perugia, Orvieto, Assisi); you’ll find this villa offers complete privacy as well as a sense of peace and tranquility to all who visit.

The Tower
Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.

In a sunny, quiet and rustic area.
The villa is located between Anghiari and Arezzo in a sunny area, absolutely quiet, with a beautiful and panoramic view on the surrounding hills. Through the accurate restoration, the house is well equipped to ensure to just a few guests absolute confidentiality, independent and comfortable stay. Exposed to the south, with independent entrance and direct access to the garden that's exclusively for our guests. Please enjoy yourself.

Villa La Doccia, Greve in Chianti
Villa la Doccia is an 8-minute drive from the center of Greve in Chianti, Località Casole, The Villa in a quiet and quiet area is located inside a small farm surrounded by vineyards and olive groves. ➡️ We would like to inform you that for this emergency we are doing everything we can to help and protect our guests by adopting a detailed and strict cleanliness. We disinfect and sanitize all parts of the house.

Quite old farmhouse on the hills of Florence
Two levels 800th rustic country house, on the hills surrounding the town with original forniture and a stunning view of the facing valley, a beautiful patio and large garden. 25 min driving from center, well placed for Chianti area, Siena, San Gimignano. 1hr driving to Pisa, Lucca, Volterra, Arezzo, Cortona and much more! Possible to have cooking class or dinners with my personal chefs Mirella and Stefano!
Popular amenities for Casentino villa rentals
Private villa rentals

La Pesa di Mezzo

Stunning Tuscan Villa & Panoramic Infinity Pool

Cipressino Villa, pool near the historic centre

La Vignaccia (Farmhouse) - villa w/private pool

Stunning house with pool, privacy and views

Podere Casina 9 - holiday home

Coaching House

Villa L'Apparita - on hilltop of Chianti
Luxury villa rentals

Tuscany Villa Mammi

Luxury Villa on Chianti Wine Estate

Casale La Querce-Tuscan Farmhouse with pool & view

Poggio Novoli 6, Emma Villas

Palazzo Gatteschi – Arezzo Città del Natale

Villa il Palagio in the Tuscan countryside

Villa Cristina Tuscany,your dream!!

Torre Rossa - Villa Tiziano with private garden
Villa rentals with a pool

Ortaglia Di Sopra Farm

Villa with pool in Chianti Area

medieval watch-tower and pool near Florence

Compound Villa Bada

Villa with Pool Casa la Quiete

Sasso Canaldo: Elegant Tuscan farmhouse

[Le rondini in Tuscany] Exclusive View Pool Villa

Il fossatino
Destinations to explore
- Cottage rentals Casentino
- Holiday home rentals Casentino
- Fitness-friendly rentals Casentino
- Rentals with lake access Casentino
- Bed and breakfasts Casentino
- House rentals Casentino
- Condo rentals Casentino
- Family-friendly rentals Casentino
- Apartment rentals Casentino
- Rentals with pools Casentino
- Pet-friendly rentals Casentino
- Rentals with outdoor seating Casentino
- Smoking-friendly rentals Casentino
- Rentals with breakfast Casentino
- Rentals with a hot tub Casentino
- Rentals with an EV charger Casentino
- Rentals with a washing machine and dryer Casentino
- Farmstay rentals Casentino
- Rentals with a fireplace Casentino
- Rentals with a sauna Casentino
- Rentals with a patio Casentino
- Rentals with a fire pit Casentino
- Villa rentals Arezzo
- Villa rentals Tuscany
- Villa rentals Italy
- 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
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Del Chianti
- Siena Cathedral
- Basilica of Santa Maria Novella
- Fiera Di Rimini
- Piazzale Michelangelo
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Riminiterme
- Piazza della Repubblica
- Pitti Palace
- Palacongressi Della Riviera Di Rimini
- Boboli's Garden
- Parco delle Cascine




