Holiday rentals in Casastieri

4.98 out of 5 average rating, 442 reviews

Home in Panzano

Old Farmhouse near Panzano Castle Abbacìo

The Abbacio apartment is part of an old farmhouse that has been restored respecting the original structure and style. Its location is just on the top of the hill, facing the valley. Surronded by vineyards and olive trees, but also attached to the village. From the house you can easily reach by feet wineries, farms and restaurants. Panzano is halfway between Florence and Siena, easily reached with car. By bus there is a good service from and to Florence, not from and to Siena. A very quiet spot!

4.96 out of 5 average rating, 165 reviews

Guest house in Macciano

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Holiday home in Poggibonsi

4.95 out of 5 average rating, 172 reviews

Vittoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

4.96 out of 5 average rating, 239 reviews

Cottage in Monteriggioni

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

4.99 out of 5 average rating, 276 reviews

Laura Chianti Holidays

Laura Chianti Vacanze is the ideal solution for those seeking peace and tranquility immersed in the Chianti countryside. The apartment, halfway between Florence and Siena, is conveniently located for quick access to Florence, Siena, San Gimignano , Volterra, as well as the beautiful Chianti hills. The apartment offers private parking, two bedrooms, a fully equipped kitchen, private bathroom, private garden, barbecue, and a wonderful view of the Chianti hills.

4.98 out of 5 average rating, 228 reviews

Apartment in Poggibonsi

Amaryllis House

Delightful two-room apartment located on the first floor in a central area. It consists of a living area with a sofa, kitchen, and laptop; a bedroom with a very comfortable double bed; a bathroom with a spacious and comfortable shower. Suitable for up to 2 people. Has a large terrace. It is a 10-minute walk to the station. Free parking in front of the house or at most within 200 m. Wi-Fi access available. You can walk to Siena Eye Laser in a few minutes.

Apartment in San Gimignano

4.93 out of 5 average rating, 118 reviews

Luxury Medieval Tower - Penthouse

Step into the past... San Gimignano Luxury Medieval Tower is right in the heart of the UNESCO town. You will be caught by the sight of San Gimignano's beautiful landscapes and at the same time you will be able to enjoy the luxury amenities of in-town living: walk downstairs to the cafes, bread shop, butcher, restaurants and local shops. Hear the church bells directly from your windows. Walking distance to all of San Gimignano main attractions.

4.91 out of 5 average rating, 324 reviews

Flat in Gavignano

Poggio Massiccioli

Accogliente appartamento per 4 persone arredato in stile toscano e con travi a vista immerso tra le dolci colline della campagna toscana. A disposizione degli ospiti giardino attrezzato,wi-fi gratuita,piscina condivisa attrezzata,forno a legna e barbecue,lavatrice. L'appartamento è stato ricavato da una graziosa casa colonica in pietra del 1800 recentemente ristrutturata secondo la tradizione toscana e suddivisa in tre comodi appartamenti.

Flat in Barberino Val d'Elsa

4.99 out of 5 average rating, 122 reviews

Apartment in Chianti at Mulino dell 'Argenna

The Roses apartment is located inside the guest house Mulino dell 'Argenna. The property was completely restored in 2015. It is a former stone mill dating back to 1400, built along the Borro dell 'Argenna course. The Mill is a lovely place, immersed in the greenery of the forest, with a beautiful park of one hectare and a large swimming pool. An ideal place to spend your days in Tuscany in complete privacy, in full contact with nature.

Superhost

Home in Poggibonsi

4.89 out of 5 average rating, 254 reviews

Tuscan Counrtry Detached House. Wi-Fi Free

Update: Air conditioning starting June 1st, 2025. Enjoy the summer with a cool breeze! Do you want to spend your holiday in a typical Tuscan barn? This is your place! Charming renovated barn for families / groups. Located in the heart of the Tuscan countryside at 2km from Poggibonsi. Ideal for a relaxing holiday and in a great location for visiting San Gimignano (13km), Siena (25km), Florence (35km).

4.92 out of 5 average rating, 107 reviews

Cozy apartment in the central area

VERY COMFORTABLE APARTMENT consisting of two bedrooms, bathroom and living room-kitchen with bright view on large terrace, located near the Siena Eye Laser clinic, downtown and main transport services, in fact it is about 600 meters from the train station and about 50 meters from the bus stop. Free parking is available for those traveling by car. Smoking is not allowed inside the apartment.

5 out of 5 average rating, 116 reviews

Villa Mocarello "IL LECCIO"

This romantic apartment is located on the second floor of a 19th century Leopoldinian Villa. The independent entrance can be reached walking through the lush garden surrounding the house. The Villa is located in a strategic position in the middle of Tuscany, close to Florence, Siena and San Gimignano. the bus station is about ten minutes on foot, the train station about fifteen minutes,

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Other great holiday rentals in Casastieri

5 out of 5 average rating, 9 reviews

Flat in Quercegrossa

Tuscany jem: La Casa del Fattore del Chianti

NickRating, 5 starstoday

A wonderful space - just tucked away from town but easy to get in. Beautiful spaces and very welcoming hosts. We had a wonderful time!

4.94 out of 5 average rating, 64 reviews

Casa Sornano - apartment with a view over Chianti

SabrinaRating, 5 stars2 weeks ago

Communication with Gael was extremely easy. Although he was out of town, co-hosts Angelo and Alessandro were super friendly and attentive. We really felt at home. We would return a million times, for sure!!!

Townhouse in Colle di Val d'Elsa

4.98 out of 5 average rating, 62 reviews

La casina sull'Elsa - Between SentierElsa and Francigena

GiorgioRating, 5 stars1 week ago

The apartment is very clean, well organized and very well stocked. The location is excellent for getting around and is well served by shops. The owners were ready to solve a problem that arose. So our opinion is excellent and certainly when we can continue to visit the beauties of Siena we will return there.

4.94 out of 5 average rating, 17 reviews

Flat in Staggia

The Optimist's House

ElenaRating, 5 stars1 week ago

It was a super pleasant stay! Daniele responds very quickly and was always attentive. He greeted us in person, helped us park right in front of the apartment, and helped us carry our bags. Once inside, he gave us a tour of the small but super cozy apartment, showing us every detail and letting us know that we had everything. Very well used! It had towels, 2 per person plus another added set. It has shampoo, gel and conditioner, I loved that detail! It has everything you could need in the kitchen, bathroom and trousseau. The area is super quiet, we slept with the window completely open and only heard the birds singing. We loved waking up to the sound of the bells in the bell tower, I wish we had that tranquility every day. The only bad thing about staying in that apartment was that we only stayed one night. I will recommend it wherever I am asked. We loved you Daniele, and your philosophy much more! Thank you!!!!

Guest suite in Poggibonsi

4.78 out of 5 average rating, 116 reviews

Santa Lucia - Siena

KiraRating, 5 stars1 month ago

We had a really nice time. The location is great for exploring Tuscany, the way to the accommodation is a bit adventurous, but you get used to it. The accommodation is very cozy and has its own charm.

4.92 out of 5 average rating, 59 reviews

Home in Poggibonsi

Agriturismo Podere San Martino (apartment for two)

LukasRating, 5 stars1 month ago

Everything was just like in the pictures. We had a great time. The view was amazing and Maddalena was really helpful. Thank you!

5 out of 5 average rating, 47 reviews

Barn in Monteriggioni

Charming Barn with Pool - Chianti Area

EricaRating, 5 stars1 week ago

Loriana’s place was impeccable. Everything as described - comfortable space, wonderful outdoor area and in a great location. But what makes it the most magical are the hosts - they are hospitable, knowledgeable of the area and make you feel part of their famiglia instantly. My daughters left calling Loriana Nonna Lori. Can’t wait to return.