
Villa Il Fedino offers luxurious suites in an elegant 14th-century building with an outdoor swimming pool. Enjoy exclusive accommodation surrounded by a green park, in the famous Chianti hills. Enjoy the Fedino's elegant charm provided by its period furniture. Each room comes with air conditioning and a satellite LCD TV. An Italian breakfast is provided daily, served on the panoramic terrace in fine weather. On request, guests can enjoy the on-site restaurant, which specialises in Tuscan dishes made from local ingredients. Staff can arrange guided tours of the Chianti area and trips to Florence and Siena. The centre of San Casciano is 200 metres away.
Exceptional
516 reviews

Set in its own large garden with views of the Chianti hills, Castello di Bibbione offers an outdoor swimming pool. Accommodation has free Wi-Fi and rooms with a satellite flat-screen TV. All apartments are decorated in a rustic style, featuring wood-beamed ceilings and terracotta floors. Each comes with a fully equipped kitchenette with a dining area. The apartments are provided with a bathroom that has either a spa bath or a shower. The Bibbione guest accommodation also produces its very own extra-virgin olive oil and Chianti wine. It is possible to organise wine tastings, or excursions with bikes provided for free by the property. In the summer you can relax in the swimming pool, or even in the garden, which offers BBQ facilities and is fully equipped with tables and chairs. It is also possible to book a massage treatment. Breakfast is available and buffet style, including sweet and savoury products. The property is located just 6 km from San Casciano In Val di Pesa. Florence Peretola Airport is a 30-minute drive away.
Exceptional
426 reviews

Villa I Barronci Resort & Spa is a charming Tuscan-style residence with private park and heated pool. It offers stunning views of the Chianti countryside, 20 minutes' drive from Florence. Rooms at I Barronci come with stonework and exposed wooden beams, and include air conditioning and a Plasma TV. The villa's panoramic outdoor pool has a hydromassage area and bar service. Featuring a panoramic sauna, the spa includes a Turkish bath, a sensory shower and a hot tub. Treatments and massages are available on request. The large sweet and savoury buffet breakfast features a variety of fresh fruit, homemade cakes and pastries as well as freshly baked pies. The Panorama restaurant offers Tuscan dishes and a long wine list. In summer you can enjoy your meals outside, with views of the valley and pool. At Villa I Barronci it is possible to rent e.bikes from May to September, to explore the surrounding olive groves and vineyards. San Casciano in Val di Pesa, where you will find shops, restaurants and cafés, is just 2 km away.
Exceptional
2327 reviews

<h2>Historic Charm</h2> Castello di Cafaggio in Impruneta is housed in a historic building, offering a unique setting with garden views. The property features a swimming pool with a view, sun terrace, and lush garden. <h2>Modern Amenities</h2> Guests enjoy free WiFi, air-conditioning, and a private pool. Additional facilities include a private check-in and check-out service, daily housekeeping, and free on-site parking. <h2>Comfortable Accommodations</h2> The villa offers family rooms with private bathrooms, a fully equipped kitchen, and a dining area. Free toiletries, a washing machine, and a TV enhance the stay. <h2>Local Attractions</h2> Located 15 km from Piazzale Michelangelo, Pitti Palace, and Strozzi Palace, Castello di Cafaggio is also close to Uffizi Gallery and Ponte Vecchio. Florence Airport is 21 km away.
Exceptional
56 reviews

A historic castle dating back to the 14th century, the Castello Di Gabbiano is set amongst 100 hectares of olive groves and vineyards. The rooms come in a Tuscan Renaissance style. Florence is 22 km away. The property is a working farm, with trekking paths amongst the vineyards. The large garden is complete with outdoor swimming pool. The rooms are charming and elegant, and feature rustic terracotta floors and wooden furniture. Air conditioning is available in the summer. Breakfast at the Castello includes Tuscan specialities, and is served in one of the drawing rooms or out in the garden. From April until November, lunch and dinner are available from Tuesday evening to Sunday evening at the restaurant 70 metres away. Wine tastings are organised daily.
Exceptional
281 reviews

I Parigi Corbinelli is surrounded by the pleasant hills at the gates of Florence. Nearby free parking and a bus stop make it ideal to visit the city. I Parigi Corbinelli - Residenza d'Epoca is a complex of buildings, the oldest of which dates back to the 14th century. The medieval tower was built on the crest of the hill and offers breathtaking views. The tranquil and homely atmosphere of I Parigi Corbinelli is ideal to experience Florence can provide, yet being far from the bustling crowds. I Parigi Corbinelli is provided with a beautiful swimming pool integrated into the beautiful natural setting. Enjoy a dip surrounded by olive trees, and admiring a magnificent view over the Certosa (monastery) and the Tuscan hills. The establishment is provided with comfortable rooms and spacious, bright superior rooms. A buffet breakfast is served outdoors during summer.
Exceptional
1062 reviews

Featuring a swimming pool with views of the Chianti Hills, Antica Pieve B & B offers Tuscan-style rooms with air conditioning and free Wi-Fi. Set in Tavarnelle in Val di Pesa, it is a 30-minute drive from Florence. Rooms at the Antica Pieve all include an LCD TV with satellite channels, a minibar and a private bathroom with free toiletries and a hairdryer. A large garden with tables and chairs is available for guests to use. A varied breakfast is served daily and, upon request, guests may also enjoy a typical Tuscan dinner. The property is 22 km from Greve in Chianti and the owners can arrange guided tours of the area, including food and wine tastings. Siena is a 40-minute drive away.
Exceptional
347 reviews

Offering a seasonal infinity pool and hot tub, Villa Le Calvane is set in Montespertoli, on the hills overlooking the Chianti region. Olive oil and wine are produced on site. Free private parking is available. Each room at this hotel is air conditioned and comes with a flat-screen TV with satellite channels. Some rooms include a seating area to relax in after a busy day. All rooms include a private bathroom with a bidet and shower, with bathrobes and slippers provided. For your comfort, you will find free toiletries and a hairdryer. Villa Le Calvane features free WiFi throughout the property. Guests can enjoy the on-site bar and restaurant offering Tuscan cuisine. Florence is 21 km from Villa Le Calvane, while Montecatini Terme is 35 km from the property. The nearest airport is Florence Airport, 17 km from Villa Le Calvane.
Exceptional
131 reviews

Set among the lush, green Tuscan hills just outside Impruneta city centre, Tenuta Torre Rossa Farm & Apartments offers spacious, comfortable apartments. Most have splendid views of nearby Florence. Self-catering apartments are bright and colourful, with floral designs, warm colours, elegant white furnishings and terracotta floors. Each apartment includes bed linen and towels. Free Wi-Fi is provided. A 19th-century country house surrounded by 20 hectares of olive groves, Tenuta Torre Rossa Farm & Apartments produces its own olive oil. The large garden features a shaded area and a swimming pool. This peaceful countryside setting is just a 10-minute drive from Florence's historic centre. Tenuta Torre Rossa Farm & Apartments provides free private parking, and public transport into Florence is available nearby. There are several dining options in the surroundings, including Tuscan restaurants, pizzerias, markets, bars, bakeries and rotisseries. Swimming pool will always be available.
Exceptional
56 reviews

COMO Castello Del Nero is set in the Chianti wine area, between Florence and Siena, and dates back to the 12th century. It features a COMO Shambhala retreat with outdoor pool and offers free parking. The uniquely designed rooms of Castello Del Nero come with original frescoes or beamed ceilings. All feature a plasma-screen TV, air conditioning, and a bathrobe and slippers. Every part of the castle offers panoramic views across the Tuscan countryside, with vineyards and olive groves. La Torre Restaurant, a Michelin-starred restaurant, is set in what was once the castle's stable. It has an à la carte menu accompanied by a selection of local wines. La Taverna Restaurant serves Tuscan specialities. Castello Del Nero offers a shuttle service to and from Florence and Sienna, which operates according to a schedule.
Exceptional
98 reviews

Surrounded by the Tuscan countryside. Il Paluffo is a 15th-century farmhouse that has preserved its historic wood-beamed ceilings and stone walls. It offers a large garden with an ecological pool. Accommodation at Paluffo conveys a rustic feel with antique wooden furniture and cotto floors. Apartments also come with a patio, a fully equipped kitchen and a living area with sofa and a flat-screen TV. This eco-friendly property was built according to the bio-architecture laws and uses solar panels. It is surrounded by olive trees and vineyards. Guests can rent bikes for free at reception and explore the surrounding nature. Otherwise they can relax on the 300 m² communal terrace furnished with sofas, tables and chairs and overlooking the landscape. Paluffo farmhouse is a 15-minute drive from Certaldo and 30 minutes by car from the medieval walled town of San Gimignano, famous for its Vernaccia white wine.
Exceptional
79 reviews

<h2>Historic Setting</h2> Agriturismo Villa Ulivello in Chianti is housed in a historic building in Strada, Italy. The property offers a garden and terrace with stunning views. <h2>Comfortable Accommodations</h2> Rooms include air-conditioning, private bathrooms, and garden views. Additional amenities feature a lounge, coffee shop, and barbecue facilities. <h2>Dining Experience</h2> The traditional restaurant serves Italian and local cuisines. Breakfast includes continental and Italian options with champagne, local specialities, and fresh pastries. <h2>Local Attractions</h2> Located 13 km from Piazza Matteotti and 23 km from Florence Airport. Nearby attractions include Piazzale Michelangelo and Uffizi Gallery.
Exceptional
232 reviews

Castello Vicchiomaggio is a historic castle dating back to the 1400s. Just outside Greve, it produces and sells its own Chianti wine. It also features a swimming pool with views across Val di Greve valley. Rooms have an elegant and classic style with terracotta floors and wooden furniture. They all come with a sofa and a satellite TV. The private bathrooms are equipped with shower and toiletries. A buffet breakfast is available every morning. The restaurant serves traditional Tuscan cuisine in a Renaissance-style dining room with arched ceilings. The Vicchiomaggio provides free parking and free Wi-Fi in public areas. It is in the heart of the Chianti wine district, 5 minutes' drive from Greve in Chianti.
Exceptional
392 reviews




Note: The prices for each boutique hotels in San Casciano In Val Di Pesa do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.
If you're considering a luxury or boutique stay in San Casciano in Val di Pesa, Italy, you're in for a treat with its rich history and stunning landscapes. Here are the top 8 attractions that you shouldn’t miss during your visit.
Castello di Bibbione: Explore the majestic Castello di Bibbione, a historic castle that offers breathtaking views and a glimpse into Tuscany's feudal past.
Pieve di San Pancrazio: Visit the Pieve di San Pancrazio, a charming Romanesque church known for its beautiful frescoes and serene ambiance, perfect for peaceful reflection.
Vignamaggio Winery: Sip exquisite wines at Vignamaggio Winery, where you can take a tour of the vineyard and indulge in tastings of some of the finest Chianti blends.
Fattoria La Ripa: Experience the authentic Tuscan countryside by visiting Fattoria La Ripa, where you can engage in local food tastings and learn about sustainable farming practices.
Ceramiche d'Arte: Discover unique handcrafted ceramics at Ceramiche d'Arte, a delightful shop offering a variety of artistic pieces that make for perfect souvenirs from your luxurious getaway.
Olive Oil Museum: Delve into the world of olive oil at the Olive Oil Museum, where you will learn about the intricate production process and enjoy tastings of premium oils.
San Casciano Market: Stroll through the vibrant San Casciano Market, held weekly, to experience local culture and taste fresh produce, cheeses, and artisan products.
Scenic Hiking Trails: Embrace the natural beauty surrounding your boutique stay in San Casciano in Val di Pesa by exploring the scenic hiking trails that offer stunning vistas of the Tuscan hills.
Transportation/Shuttle service is available at the following boutique hotels in San Casciano in Val di Pesa:
A spa is available to guests at the following boutique hotels in San Casciano in Val di Pesa:
Families traveling in San Casciano in Val di Pesa enjoyed their stay at the following boutique hotels:
Some of the best boutique hotels in San Casciano in Val di Pesa are: