
Villa vacation 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.

Tuscan charm of villa - countryside - Villa Senaia
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

The Lazy Oak
Perched on a hillside above the Valdarno area, between the cities of Florence, Arezzo and Siena, the Lazy Oak villa is surrounded by acres of olive groves. The main house on two level has been fitted with bedrooms, bathrooms and new kitchen whilst retaining its old terracotta floors and beamed ceilings. A dining loggia for al fresco meals enjoys a breathtaking view of the countryside. The infinity pool is set just a few steps from the house on a green terrace furnished with loungers.

The Tancherina, a Tuscan heart
La Tancherina Detached house in a small village of 4 buildings in the Tuscan countryside in the municipality of Figline and Incisa Valdarno (FI). At the center of the Florence, Siena, Arezzo triangle, it is a perfect starting point for cultural, food and wine, and spa itineraries. It is surrounded by a large garden with loggias for summer lunches, and large terraces for sunbathing. It is also equipped with outdoor furniture and an outdoor hot tub, usable in all seasons

Villa La Doccia, Greve in Chianti
Villa La Doccia is located about an 8-minute drive from the center of Greve in Chianti, in the area of Casole, in the heart of the beautiful Chianti countryside. The villa is located in a quiet and peaceful area, on a small farm surrounded by vineyards and olive groves, where guests can enjoy nature and the typical Tuscan landscapes. The location is ideal for those who want to relax in the countryside but at the same time be close to the center of Greve in Chianti.

Il Vichiaccio: Accessible Chianti Villa & Jacuzzi
Cozy Chianti getaway near Florence. This 135sqm stone house has a rustic kitchen with a fireplace. It sleeps 9 guests in 3 rooms, but for groups of 11, a 4th bedroom is included. Smaller groups can add it for extra comfort (extra fee). Enjoy the private garden with a covered dining area, a patio with armchairs and parking. The ground floor is fully wheelchair-friendly (kitchen, bedroom, bath). Plus, A/C and a private Jacuzzi (extra fee) for relaxing under the stars!

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.

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.

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.

Farmhouse on Florence hill
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. 15 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!

"Villa Daisy" overlooking Siena
Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Agriturismo Podere Scaluccia Chianti, Florence
The farmhouse is located 15 minutes (8 km) from the center of Florence, a city rich in art and culture, and is surrounded by beautiful panoramic views of the hills, at the entrance to Chianti. The house is old: traditional materials such as stone, wood and terracotta are the main features. The outdoor garden is available to everyone! To learn more, search for Podere Scaluccia
Popular amenities for Casentino villa rentals
Private villa rentals

Charming Chianti Villa | Garden & Panoramic Pool

Villa Il Tollino

romignano wine farm

Fattoriafontenovo, country house Perugia, Umbria

Luxury Villa in Chianti • Private Natural Pool

Poggelleri the postcard on Poppi and Tuscan hills

The twigs

Villa Montanina - exclusive relaxation in Tuscany
Luxury villa rentals

Villa Holm stunning view 10 mn walk to city centre

Villa Siveri - private swimming pool - air con

Cipressino Villa, pool near the historic centre

Charming Tuscan retreat: spa, pool & cinema

Villa with swimming pool surrounded by Florentine nature

Stunning house with pool, final summer discounts

Villa il Palagio in the Tuscan countryside

Villa Isabella
Villa rentals with a pool

Lake View Private Villa w Pool

Casale La Querce-Tuscan Farmhouse with pool & view

Gorgeous view on vineyards, Stone Tuscan private V

Private Villa with swimming pool in Tuscany

Villa Cristina Tuscany,your dream!!

LUXURY VILLA BELVEDERE - Sea View with Pool & Spa

Villetta dei Fagiani - pools, Jacuzzi in Florence

Tuscany View - Villa Arianna
Destinations to explore
- Pet-friendly rentals Casentino
- Apartment rentals Casentino
- Rentals with a fireplace Casentino
- Rentals with lake access Casentino
- Bed and breakfasts Casentino
- Family-friendly rentals Casentino
- Vacation home rentals Casentino
- Cottage rentals Casentino
- Condo rentals Casentino
- House rentals Casentino
- Fitness-friendly rentals Casentino
- Rentals with a fire pit Casentino
- Rentals with pools Casentino
- Smoking-friendly rentals Casentino
- Rentals with a hot tub Casentino
- Rentals with breakfast Casentino
- Rentals with a patio Casentino
- Rentals with outdoor seating Casentino
- Rentals with an EV charger Casentino
- Rentals with a washer and dryer Casentino
- Rentals with a sauna Casentino
- Farmstay rentals Casentino
- Villa rentals Arezzo
- Villa rentals Tuscany
- Villa rentals Italy
- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Pinarella Di Cervia
- Basilica of Santa Maria Novella
- Mugello Circuit
- Fiera Di Rimini
- Mirabilandia
- Misano World Circuit
- Mercato Centrale
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Stazione Santa Maria Novella
- Piazza della Repubblica
- Del Chianti
- Autodromo Enzo e Dino Ferrari
- Piazzale Michelangelo
- Parco delle Cascine
- Palacongressi Della Riviera Di Rimini
- Pitti Palace
- Palazzo Vecchio





