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Holiday rentals in San Casciano In Val di Pesa

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Quick stats about holiday rentals in San Casciano In Val di Pesa

  • Total holiday rentals

    Explore 30 holiday rentals in San Casciano In Val di Pesa

  • Nightly prices starting at

    San Casciano In Val di Pesa holiday rentals start at £45 per night before taxes and fees

  • Verified guest reviews

    Over 960 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of San Casciano In Val di Pesa holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across San Casciano In Val di Pesa rentals

  • 4.9 Average rating

    San Casciano In Val di Pesa stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated holiday rentals in San Casciano In Val di Pesa

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Apartment
5 out of 5 average rating, 340 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful Chianti hills in Tuscany, with the possibility of organising a shuttle service and exclusive experiences tailored to your needs. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle, hills and vineyards with unique sunsets.

Guest favourite
Apartment
5 out of 5 average rating, 14 reviews

Casina a Mezzanotte (San Casciano in Val di Pesa)

Have you always dreamed of staying in a small Tuscan village? Our house is located in the village of San Casciano Val di Pesa, in the heart of Chianti Classico. The village is equipped with numerous restaurants, bars, and shops. We are located 20 minutes from Florence and 40 minutes from Siena. The apartment located on the first floor without an elevator consists of: - Bright open space living room - Double Room in mezzanine (Crib available) - Full bathroom - No Kitchen Ideal for a romantic holiday.

Top guest favourite
Townhouse
4.89 out of 5 average rating, 333 reviews

Florence Sunset Hills • Giogoli

Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Top guest favourite
Home
5 out of 5 average rating, 17 reviews

Villa la scuderia quiet luxury private garden pool

Once a 19th-century horse stable, this Tuscan home was discovered by my mother : a Dutch artist and traveller, she moved here in search of beauty, nature and light. She stayed for twenty years. My brother and my daughter grew up running barefoot on these ancient terracotta floors. Even today I still fall in love with the light that enters through the old arches and reflects into the house and the flower-filled private garden.its not an hotel is a lifetime experience, welcome to” La scuderia “.

Top guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home
4.98 out of 5 average rating, 238 reviews

The Chianti Classico Sunset

If you are looking for an idyllic location in the heart of the Chianti Classico region, surrounded by the vineyards and olive groves of the beautiful Tuscan hills, on the estate of a historic 16th-century villa, then come to our barn!! It has a dominant position with an amazing view, where you can enjoy breathtaking sunsets. The complete independence of the house, the cosy garden and the large loggia allow you to enjoy your stay in total tranquillity. Our reviews are your best guarantee.

Top guest favourite
Villa
5 out of 5 average rating, 8 reviews

The Cetine

Exclusive historic 14th-century residence in the Chianti Classico area, 10 km from Florence. An oasis of peace, surrounded by a large fenced private garden and by olive groves, vineyards and woods. Great location for visiting Florence, Pisa, Siena, Lucca, Arezzo, San Gimignano, etc. They are all within an hour's drive. If you are interested, we will be happy to recommend restaurants and an independent home chef service so you can enjoy a traditional meal right in the peace of the villa.

Guest favourite
A dining table is set under the shade of lush trees, featuring a bottle of wine and glasses. The surrounding garden is filled with tall cypress trees and vibrant greenery, creating a serene atmosphere for outdoor dining.
Farm stay
4.77 out of 5 average rating, 168 reviews

Sperone: two floors apartment with pool

Just a few km from Florence and surrounded by vineyards and olive groves of the Principe Corsini estate, this is the ideal place for a classic Tuscan-style holiday in the heart of Chianti Classico. The private garden, which also provides access to the pool at Villa Le Corti, is ideal for relaxing and peaceful al fresco dining. The pool, open from June to September, has a breathtaking view of Tuscan rolling hills. The property includes a parking area reached from the entrance gate.

Guest favourite
A traditional farmhouse features a warm exterior with vintage red shutters. Surrounding flower pots add a touch of greenery. A hanging metal jug is visible in the foreground, framing the scene, while the entrance is marked by a welcoming open door.
Farm stay
4.81 out of 5 average rating, 320 reviews

Your home in the heart of Chianti area!

The apartment is located in the heart of Chianti, just 2 km from the center of San Casciano VP, 17km from Florence and 50km from Siena. It is self catering (36 square meters) and has a separate entrance, bedroom, bathroom with shower and fully equipped kitchen. It overlooks a panoramic terrace where a BBQ is available. It is located inside a local farm , still familiar managment ,that produces wine and olive oil. During your stay you can visit the cellars and taste the products.

Top guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home
5 out of 5 average rating, 223 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top guest favourite
Flat
4.89 out of 5 average rating, 194 reviews

Timeless Beauty in Chianti | 20 min da Firenze AC

Experience the Tuscan dream in this restored Casa Colonica. Surrounded by a private olive grove with panoramic views of San Casciano, you’re just 20 min from Florence. The Space: Bright 2BR apartment with silent AC, fast Wi-Fi, and a full kitchen. Ideal for families or remote work. Outdoor Living: Relax under our grape pergola or explore the olive trees. Logistics: Includes secure gated parking (perfect for rentals) and easy bus/car access to Florence, Siena, and Chianti.

Top guest favourite
Bright seating area features two white armchairs and a patterned ottoman, surrounded by large glass arches that open to a lush garden. Natural light floods the space, enhancing the exposed stone walls and wooden ceiling beams, complemented by a large potted plant.
Villa
4.97 out of 5 average rating, 119 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.

Top guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay
4.99 out of 5 average rating, 475 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Popular amenities for San Casciano In Val di Pesa holiday rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in San Casciano In Val di Pesa?

    San Casciano In Val di Pesa has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in condo rentals in San Casciano In Val di Pesa?

    Experience the best of San Casciano In Val di Pesa with our condo rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in San Casciano In Val di Pesa?

    Four-legged friends are welcome in San Casciano In Val di Pesa. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in San Casciano In Val di Pesa?

    Yes! Work meets play with ease at over 10 vacation rentals in San Casciano In Val di Pesa featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in San Casciano In Val di Pesa have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in San Casciano In Val di Pesa. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in San Casciano In Val di Pesa have a kitchen?

    Absolutely! We offer over 10 condo rentals with a kitchen in San Casciano In Val di Pesa. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in San Casciano In Val di Pesa have wifi?

    Absolutely! We offer over 10 condo rentals with wifi in San Casciano In Val di Pesa. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in San Casciano In Val di Pesa have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in San Casciano In Val di Pesa. Enjoy a tailored experience with all the comforts you desire.