Villa vacation rentals in San Casciano In Val di Pesa

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

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Superhost

Villa in Siena

4.8 out of 5 average rating, 267 reviews

XIII Century Tower with Private Panoramic Pool

Ancient country tower property with 5 airconditioned bedrooms for up to 10 guests at the heart of the peaceful Montechiaro organic wine estate. From your private pool, soak in the Tuscan sun and enjoy unforgettable views of the Chianti rolling hills and the medieval towers of Siena. The property also boasts access to the endless olive grove, a large patio area for outside dining in the shade, ping pong table for fun family matches, WIFI & free parking. Silence and time are the real luxury here.

Top guest favorite

An aerial view captures the expansive Poggio del Fattore estate, showcasing lush greenery and neatly arranged olive trees. The two main buildings, characterized by terracotta roofs, are complemented by the blue of the swimming pool, surrounded by vibrant gardens and cypress trees.

Villa in San Leolino

5 out of 5 average rating, 105 reviews

Poggio del Fattore-Villa with pool, hilltop, Chianti

Poggio del Fattore is situated at the eastern edge of the Chianti region in Valdambra, a green valley that joins the lands of Florence, Siena and Arezzo. The farmstead is on the top of an hill and lies at the end of a long private road through a large olive growing estate; therefore you absolutely need a car. The breathtaking landscapes and the location of the villa offer the privacy needed for a peaceful and relaxing holiday and a perfect departure point from which to explore central Tuscany.

Superhost

A serene outdoor pool is surrounded by landscaped gardens and trees, illuminated by soft lighting. Sun loungers and umbrellas provide shade, while a wooden railing enhances the scenic view of the surrounding Tuscan landscape under a twilight sky.

Villa in Monsummano Terme

4.82 out of 5 average rating, 51 reviews

Florence & Tuscany. Pool, jacuzzi, parking & relax

Charming 15th century Tuscan Villa, 5bdr, restored respecting local traditions, fenced and furnished with international taste. A 360° view and exclusive comfort. Strategic position -in the heart of Tuscany- 10 minutes from Thermal Spa "Grotta Giusti" and from the motorway, to easily reach Florence, Lucca, Pisa, Siena, beaches & Cinque Terre. Surprising, 30 steps away: you can discover a restaurant of excellence, for unforgettable dinners. We are absolutely certain: it will not disappoint you!

Superhost

A serene pool area features a clear blue swimming pool surrounded by lush greenery and blooming flowers. A natural stone waterfall adds a calming element, while nearby, vibrant plants line the edges, enhancing the peaceful outdoor setting.

Villa in Castelnuovo Berardenga

4.72 out of 5 average rating, 32 reviews

Private Villa: Panoramic Pools and Wellness

la Villa è immersa tra le vigne e gli olivi: Siamo nel cuore del chianti storico ma in posizione strategica per raggiungere Siena , Firenze e San Gimignano. Ideale per riunioni familiari, piccole cerimonie, pizza party nel forno a legna o rilassarsi nella spaziosa piscina con splendida vista.Sempre ad uso esclusivo degli ospiti una suggestiva Spa all'interno di una loggia panoramica, direttamente collegata con la casa, con bagno turco, sauna, Jacuzzi e sala massaggi.

Top guest favorite

Villa in San Casciano

4.97 out of 5 average rating, 108 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 favorite

The villa, constructed from warm stone, is positioned amidst lush hills. It features a panoramic pool with sun loungers and umbrellas, surrounded by greenery. An outdoor pergola provides shaded seating, while ample parking is located nearby.

Villa in Radicondoli

5 out of 5 average rating, 8 reviews

Villa PoggiAlto, panoramic pool and spa in Tuscany

Villa PoggiAlto, recently renovated residence, with materials for incomparable luxury and comfort. It is located in the province of Siena, in a dominant position on the top of a hill. Its large panoramic swimming pool and wonderful spa will offer an unforgettable holiday in both summer and winter. Villa Poggialto is the ideal place for those who want to spend a holiday in Tuscany full of culture, nature, relaxation and good food with friends and family.

Superhost

A charming stone villa is framed by lush greenery and vibrant flower beds. The building features three arched windows with planters, a terracotta roof, and steps leading to the entrance. The expansive lawn offers a serene atmosphere, complemented by distant views of the rolling hills.

Villa in Radicondoli

4.94 out of 5 average rating, 18 reviews

A Romantic Villa in the heart of Tuscany

The old country villa is the ideal location for an unforgettable vacation, suitable for families and small groups: where you can rest and enjoy the fresh and spacious interiors, the shade of the loggia and the scent of the aromatic herbs in the wide garden. Where you may work, read, write and relax in a peaceful atmosphere, visit the nearby artistic cities, take quiet walks or a gourmet tour through the many trattorias of the area.

Superhost

A spacious outdoor patio features comfortable lounge chairs and a woven seating arrangement, overlooking lush, rolling hills. Natural greenery frames the view, contributing to a peaceful setting under a clear blue sky.

Villa in Montescudaio

4.8 out of 5 average rating, 10 reviews

PRIVATE VILLA BERTI TUSCANY FOREVER Montescudaio

Villa Berti TUSCANY FOREVER. This is standalone, new villa with private swimming pool and 3 bedrooms and 2 bathrooms. WE KNOW WHERE HAPPY KIDS ARE ! TUSCANY FOREVER featuring unique family friendly properties. Berti is located 2km from the center of Montescudaio town with magnificent views. Etruscan coast , the sea is about 10km away. If you’re facing an issue that requires a personal touch, please contact us.

Guest favorite

An inviting indoor hot tub is highlighted, featuring sleek white surfaces and wooden accents. Two glasses of white wine and a tray of fresh raspberries are placed nearby, enhancing the relaxing ambiance of the space.

Villa in Monteroni d'Arbia

4.95 out of 5 average rating, 131 reviews

"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).

Top guest favorite

Villa in Orentano

4.96 out of 5 average rating, 100 reviews

Charming Villa in Stone in Tuscany, Borgo ai Lecci

The location, easily accessible, is perfect for visiting the main attractions in Tuscany: the cities of art, the old villages, beautiful landscapes and many other points of interest in this amazing region. Or relax and feel like you are at home. This charming well-maintained Villa in Stone is part of a complex of three buildings used for higher-level holiday homes.

Guest favorite

A well-maintained garden surrounds the entrance of the villa, featuring a variety of greenery and flowering plants. A paved pathway leads to the door, with a small seating area visible just beyond it. Solar panels are installed on the roof, emphasizing sustainability.

Villa in Figline e Incisa Valdarno

5 out of 5 average rating, 26 reviews

Villa Siveri - private swimming pool - air con

Affascinante e lussuosa villa con piscina privata. Grandissima villa con cucina, sala da pranzo, sala con caminetto, 2 camere matrimoniali, 1 camera singola , 1 camera con letto alla francese, 1 divano letto matrimoniale nel soggiorno al primo piano (tra le due camere), 2 bagni di cui uno con vasca idromassaggio e uno con doccia.

Superhost

A serene outdoor area features a private swimming pool surrounded by lush greenery. Two lounge chairs and a small table are positioned beside the water, offering a relaxing space. The villa stands in the background, framed by trees and garden foliage.

Villa in Montopoli

4.81 out of 5 average rating, 53 reviews

Villa Belvedere beautiful view surrounded by greenery

My place is close to art and culture, great views, family-friendly activities, restaurants and the beach. You'll love my place because of its atmosphere, outdoor spaces, and light. My accommodation is suitable for couples, solo adventurers, business travellers, families (with children) and furry friends (pets).

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What guests are saying

Charming property, wi-fi, weddings ,cooking class

4.96 out of 5 average rating, 23 reviews10 months ago

Our wedding at Villa Cini was truly magical. The venue’s blend of natural beauty and elegance provided the perfect backdrop for our stay during the week and our special day. The gardens and stunning views created a fairy tale atmosphere and allowed to us have both an Indian wedding and an Italian Civil one. The arches ballroom, offered a romantic and inviting ambiance. We are incredibly grateful to have a chosen a place which has passed down for generations and has such a heartfelt attention to detail. If you're looking for a dream wedding venue and a beautiful place to stay then look no further than Villa Cini.

Villa in Bucine

What guests are saying

Elegant Chianti Villa w/ Stunning Views + Starlink

4.89 out of 5 average rating, 9 reviews7 months ago

What a great place. Very quiet and beautiful views. We had a great time. We loved the serenity of the place. You do not hear anything but your own breathing😊. I can definitely recommend this house. You reach the house of road but that has its charme too!

Villa in Castelnuovo Berardenga

What guests are saying

Villa Angiolina

4.9 out of 5 average rating, 39 reviews6 months ago

Villa Angiolina is truly beautiful!!! The view is incredible and everything was spotless and beautifully decorated. Our host was lovely and gracious and responded very quickly to all communications. She even arranged for an amazing pizza party with a private chef that was just one or the memorable moments from our time at the Villa. If this Villa is available…just book it!!! You will be glad that you did!!!!

Villa in Montecucco

What guests are saying

Exclusive Villa with Private Pool and Air Cond.

4.82 out of 5 average rating, 17 reviews10 months ago

Our stay at Villa Chiara was nothing short of delightful. Nestled in the hills it offered a picturesque view of the Tuscan countryside. The villa itself was spacious and well maintained. It felt like home away from home. The pool and back patio are surrounded by lovely flowers, herbs and olive trees. Offering a spectacular view of the evening sunsets. The location was perfect to take short day trips to Siena, Florence and Montepulciano. Highly recommend for a serene, peaceful and relaxing getaway.

Villa in Pergine Valdarno

What guests are saying

entire private accommodation

5 out of 5 average rating, 15 reviews7 months ago

Villa Bellavista is a true gem in the heart of Chianti Classico. Its location, overlooking the beautiful "Conca d'oro" valley, offers stunning views and unforgettable sunsets. Surrounded by olive trees and vineyards, the villa provides complete privacy and peace. The spacious interior, with a large kitchen, comfortable bedrooms, and a fully equipped bathroom, ensures a relaxing stay. The host was very helpful and always available. He provided a secure space to store our bikes, which was very convenient. The outdoor area, with a pool and relaxation space, is perfect for enjoying the Tuscan sun. The property is well-secured, making it ideal for guests with pets. The walk to Panzano in Chianti takes just a few minutes. Overall, this place is a perfect getaway with breathtaking scenery and a welcoming atmosphere. Highly recommended!

Villa in Panzano

What guests are saying

STUNNING 5BR VILLA WITH POOL IN CHIANTI TUSCANY

4.78 out of 5 average rating, 23 reviews6 months ago

A perfect Tuscany stay☀️☀️ Upon arrival, Giovanni was waiting for us with a big smile. He showed us around and gave us the info we needed to use the facilities. He was very helpful, and assisted us with driving us to the grocery store and back to the house the night we arrived. The house was super cosy, and had everything we needed for the stay. Well furnished, lot of kitchen utensils, and In the other house - there were a washing machine and a tumble dryer. The housemaid brought us fresh clean towels after 2 nights. Everything was really nice. Enjoyed our stay to the maximum. It’s a 15 minute walk down to Grece centrum, so no problem to buy groceries and walk back up if you are a group. The pool was nice, and the bedrooms were cosy. We would definitely go back to this place again. Thanks for the wonderful stay!!!

Villa in Greve in Chianti

What guests are saying

Villa Sunkiss: Luxury Farmhouse with Tuscan Flair

4.86 out of 5 average rating, 7 reviews3 weeks ago

We were in the villa with 6 adults and a toddler. The location is quiet and in the beautiful hilly landscape of Tuscany (you need a car). The villa is very valuable and beautifully decorated, you feel very comfortable very quickly. One of the three bedrooms is a little smaller and does not have a real wardrobe, but the other two rooms are spacious and with plenty of storage. The outdoor area is also very spacious. We didn't use the pool much because it was still a bit too cold, but the whole area invites you to relax!! All in all we had a wonderful vacation, can fully recommend the villa and would love to come back again!

Villa in Montecarlo

What guests are saying

Villa La Poggerina, private pool and amazing view

4.97 out of 5 average rating, 37 reviews7 months ago

A rare circumstance where both property and hosts exceeded our expectations. The house is spacious with lovely views and a patio and pool for exclusive use by guests. It is well stocked and appointed, including a pool table and multi-game arcade machine. Much appears recently renovated. For those wanting to cook traditional wood-fired pizzas, there are two outdoor ovens, plenty of wood, and a host at the ready to provide assistance as needed. Emanuele and his wife are excellent hosts - gracious and welcoming yet non-intrusive. They had a fantastic charcuterie board and wine ready on our arrival and helped us with guidance and reservations multiple times throughout the week. They live in the house next door, but you wouldn't know it. All in all, one of our best AirBnB experiences in nearly a decade of stays - very highly recommended!

Villa in La Poggerina

What guests are saying

Luxury villa in Tuscany Panzano in Chianti

4.92 out of 5 average rating, 25 reviews3 weeks ago

This Airbnb was a dream—beautiful, serene, and surrounded by stunning countryside views. The house itself was charming and comfortable, offering total relaxation while still being just a short drive from town for incredible food and wine. A perfect balance of tranquility and adventure!

Villa in Greve in Chianti

What guests are saying

Panoramic" Casa Gello" with private pool.

4.93 out of 5 average rating, 70 reviews7 months ago

Casa Gello is a fantastic holiday home. It is beautifully situated in the hills overlooking the surrounding valleys, with a great view of San Gimignano. Walks or just chilling; everything is possible. Certaldo & Castelfiorentino with shopping options and supermarkets is not far; There are numerous restaurants - from pizza to traditional Tuscan dishes. Excursions to the surrounding cities, for example Siena, San Gimignano, Florence, Volterra, Pisa etc. are no problem by car or using the local train station in Certaldo with easy parking facilities. The landlord Monica is very nice and gave me plenty of information beforehand and during the stay. The house is a clear recommendation if you like to experience the true Tuscan holiday feeling.

Villa in Castelfiorentino

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