
Villa holiday rentals in San Casciano In Val di Pesa
Find and book unique villas on Airbnb
Quick stats about villa rentals in San Casciano In Val di Pesa

Nightly prices starting at
San Casciano In Val di Pesa holiday rentals start at £1,135 per night before taxes and fees

Verified guest reviews
Over 110 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across San Casciano In Val di Pesa rentals

5 Average rating
San Casciano In Val di Pesa stays are highly rated by guests – averaging 5 out of 5!
Top-rated villa rentals in San Casciano In Val di Pesa
Guests agree: these villas are highly rated for location, cleanliness and more.

Tuscany Country House Villa Claudia
Experience the enchantment of our Country House: a prestigious old Tuscan farmhouse, finely restored, with breathtaking views of the village of Canneto (785 AD). Surrounded by the greenery of San Miniato and equipped with every modern luxury, the villa is an exclusive retreat for regeneration. Choose between total relaxation in the Jacuzzi in the garden, excellent food and wine tours or visits to the nearby Tuscan cities of art. An unforgettable sensory experience between history and nature. Book your dream holiday in Tuscany!
4.94 out of 5 average rating, 134 reviews
Manor House - IlVillinoFarmhouse
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
4.93 out of 5 average rating, 256 reviewsLe Maggioline Your Tuscany country house
Nestled among serene olive groves, this charming, fully renovated Italian home combines rustic elegance with modern amenities, making it the perfect retreat. The house features four en-suite bedrooms with stunning panoramic views, a spacious terrace with a covered veranda for al fresco dining, a BBQ, and a newly updated saltwater pool (2023), open mid-April to October. Guests rave about evenings at the long table, savoring local wines while watching breathtaking sunsets. A true Tuscan escape!
4.98 out of 5 average rating, 142 reviews
Casa de' Miei – Garden Villa near Florence, Chianti
"Casa de' Miei" is a detached villa with a large garden, surrounded by greenery, just outside Impruneta, halfway between Florence and Chianti Classico. A typical Tuscan house, with traditional terracotta floors, ceilings with exposed beams, 4 double bedrooms, 3 bathrooms and a beautiful veranda. The garden is equipped with a barbecue, wood-burning oven, ping pong, table soccer, and a relaxation area among roses and lemons. We welcome all travelers looking for an oasis of peace in Tuscany!
5.0 out of 5 average rating, 102 reviews
CasaDiManuela:TotallyPrivateChiantiVilla withTub
CasaDiManuela:TotallyPrivateVilla in Chianti withTub Jacuzzi The villa, immersed in the Chianti countryside, was obtained from an old farmhouse and then renovated with extreme care and attention to detail. Original terracotta floors and ceilings with ancient exposed beams, old traditional Tuscan furniture, flowery fabrics that dress beds and armchairs, paintings, antique china and lived objects recovered from markets and junk dealers will frame your living room. Nothing here is by chance.
4.97 out of 5 average rating, 106 reviews
Put down your luggage, this is just the beggining!
Il Mulino, a charming former mill turned country house, is a tranquil retreat perfect for families and friends. The villa offers 4 inviting bedrooms and ample space for relaxation, both indoors and out. On warm days, guests can enjoy the swimming pool with its integrated jacuzzi. Bordering a picturesque winery, the property provides beautiful views of the vineyards. Nestled in the valley, it’s a 15-minute walk to the heart of Greve in Chianti and a 30-minute drive to Florence.
4.89 out of 5 average rating, 99 reviews
Villa L'Olivo w/Private pool (Close San Gimignano)
Villa L'Olivo is located in the Tuscan countryside, about 10 kilometers from San Gimignano and a few minutes from the supermarkets and various services in Poggibonsi. Our Villa is a great starting point to discover all the beauty of Tuscany, but it is also an ideal place for those who love to take a break from the hectic life of the city. At Villa L'Olivo, you can book a dinner with a private chef, directly in the villa, to enjoy a Tuscan dinner in peace. Write to us for info!
4.99 out of 5 average rating, 101 reviews
Il Vichiaccio: Florence Villa with Jacuzzi
Cozy Chianti Villa close to 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!
4.95 out of 5 average rating, 202 reviews
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.
4.98 out of 5 average rating, 107 reviews
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.
4.98 out of 5 average rating, 120 reviews
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.
5.0 out of 5 average rating, 190 reviews
Farmhouse in Chianti
Beautiful portion of a farmhouse immersed in Chianti with a beautiful swimming pool, surrounded by vineyards and olive trees, perfectly furnished with a large garden and parking spaces. It is located 20 minutes from Florence, 40 from Siena and 50 from Pisa, in a few minutes you can reach Certaldo (birthplace of Boccaccio) and Vinci (birthplace of Leonardo Da Vinci). The house is halfway between Montespertoli and San Casciano (7km).
4.95 out of 5 average rating, 221 reviewsPopular amenities for villa rentals in San Casciano In Val di Pesa
Private villa rentals

Villa Capanna, Private Pool, Breathtaking Views
4.89 out of 5 average rating, 309 reviews
Villa of the 2 Olive Trees (Abbadia Isola)
4.97 out of 5 average rating, 174 reviews
Ancient Villa with Tower
5.0 out of 5 average rating, 10 reviews
Villa il Giglio Spacious Tuscan Retreat inChianti
4.91 out of 5 average rating, 35 reviews
Badia a Passignano Guard
4.86 out of 5 average rating, 7 reviews
[Villa Acquapietra Florence] Pool in Countryside
4.89 out of 5 average rating, 72 reviews
Florence Chianti Art Villa
5.0 out of 5 average rating, 36 reviews
The Cetine
5.0 out of 5 average rating, 14 reviewsLuxury villa rentals

Farmhouse on Florence hill
4.98 out of 5 average rating, 147 reviews
Poggio del Fattore-Villa with pool, hilltop, Chianti
4.99 out of 5 average rating, 131 reviews
Villa with pool in Chianti Area
4.95 out of 5 average rating, 73 reviews
THE CASTELLACCIO CYPRESSES (Cip 1 + Cip 2)
5.0 out of 5 average rating, 17 reviews
Villa Montemaggio
4.86 out of 5 average rating, 35 reviews
Stalla - Villa with garden in the historic center
4.86 out of 5 average rating, 44 reviews
Luxe Estate nr Florence. Vineyard, Pool, Privacy
4.97 out of 5 average rating, 73 reviews
Exclusive Tuscan Villa with private pool
5.0 out of 5 average rating, 16 reviewsVilla rentals with a pool

Villa La Doccia, Greve in Chianti
4.85 out of 5 average rating, 180 reviews
Villa with pool near the center of Florence
4.9 out of 5 average rating, 84 reviews
Villa Gelsomino, your dream in Tuscany
4.94 out of 5 average rating, 32 reviews
La Cipresseta Estate | Cipresso House
4.98 out of 5 average rating, 41 reviews
Romantic accomodation within Tuscan hills
4.81 out of 5 average rating, 21 reviews
Villetta dei Fagiani - pools, Jacuzzi in Florence
4.86 out of 5 average rating, 14 reviews
Tuscany Villa + private pool and garden estate
5.0 out of 5 average rating, 43 reviews
Sestuccia
4.99 out of 5 average rating, 76 reviewsDestinations 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)
- Stazione Santa Maria Novella
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Val di Luce
- Pitti Palace
- Boboli's Garden
- Porta Elisa





