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Holiday houses 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 $84 AUD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of San Casciano In Val di Pesa holiday rentals include Wi-Fi 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
Home in Greve in Chianti
4.99 out of 5 average rating, 111 reviews

Relaxation and charm in the Chianti hills

Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

Guest favourite
Condo in San Casciano In Val di Pesa
4.88 out of 5 average rating, 16 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.

Superhost
Townhouse in Scandicci
4.88 out of 5 average rating, 338 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
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 in San Casciano In Val di Pesa
4.98 out of 5 average rating, 241 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 welcoming garden and the large loggia allow you to enjoy your stay in total tranquillity. Our reviews are your best guarantee.

Superhost
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 in San Casciano In Val di Pesa
4.77 out of 5 average rating, 171 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 in San Casciano In Val di Pesa
4.8 out of 5 average rating, 324 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.

Superhost
Apartment in San Casciano In Val di Pesa
4.89 out of 5 average rating, 199 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
A heated jacuzzi is situated under a shaded pergola, surrounded by lush greenery and colorful flowers. The serene outdoor space is complemented by a gravel path leading towards vineyards in the background, inviting relaxation and privacy.
Villa in San Casciano In Val di Pesa
4.95 out of 5 average rating, 202 reviews

Il Vichiaccio: Florence Villa with Jacuzzi

Cozy Chianti Villa 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!

Top Guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 104 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.

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 in San Casciano in Val di Pesa
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.

Guest favourite
The villa is set within a lush garden filled with greenery and flowering plants. A decorative fountain is visible in the foreground, surrounded by elegant outdoor seating. The villa's white exterior and green shutters complement the tranquil, nature-filled environment.
Villa in San Casciano In Val di Pesa
5.0 out of 5 average rating, 10 reviews

Ancient Villa with Tower

A historic villa built in the 16th century, elegant and finely furnished, it is strategically located for your stay in Tuscany. The beautiful garden and park surrounding it make it a place of great peace and relax. It can be rented whole, with the large living room, eat-in kitchen, dining room and 4 double rooms with en suite bathrooms, or individual rooms, with use of the kitchen upstairs next to the rooms (Room the Cedar, Suite, of the Flowers, Deco).

Superhost
An aerial view showcases a 16th-century estate surrounded by lush, rolling hills, Chianti vineyards, and olive groves. Neatly arranged cypress trees line the property, while a serene pool is visible among the vibrant greenery, contributing to the tranquil setting.
Apartment in San Casciano In Val di Pesa
4.95 out of 5 average rating, 39 reviews

Air Suite at Villa Santa Lucia Nuova

Suite Aria is one of four exclusive apartments at Villa Santa Lucia Nuova, a beautifully restored 16th-century estate nestled in the rolling hills of Tuscany. Surrounded by Chianti vineyards, cypress trees, and olive groves, it offers the perfect blend of historic charm and modern comfort. Whether you're seeking a romantic escape, a family holiday, or a peaceful retreat, Suite Aria is an ideal base for an authentic and unforgettable Tuscan experience.

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 apartment rentals in San Casciano In Val di Pesa have wifi?

    Absolutely! We offer over 10 apartment 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.