Holiday houses in Cipressino

Farm stay in San Gimignano

4.89 out of 5 average rating, 209 reviews

Oleandro double room with pool in San Gimignano

Double room in the peaceful countryside of San Gimignano, just 5 min from town by car. Located in Montegonfoli Farm, an ancient estate like a hidden hamlet, surrounded by olive trees, vineyards, and a private forest with a stream. Guests can enjoy the pool during the warm season. The room has a 160x190cm queen bed, large bathroom, fridge, microwave, and a terrace with dining table (no kitchen/fires). A perfect place for couples or solo travelers seeking tranquility, charm, and a touch of Tuscany

4.96 out of 5 average rating, 165 reviews

Guesthouse 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, 173 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.

4.75 out of 5 average rating, 136 reviews

"Nel cuore di Poggibonsi"

Nostro piccolo appartamento si trova nel proprio centro storico della città. In una bella piazzetta con ristoranti di tipica cucina Toscana. A pochi passi dalla stazione degli autobus e del treno, solo 5 minuti a piedi. Immediatamente vicino ad un piccolo centro commerciale. A 10 mt un parcheggio a disco orario e un altro gratuito alla stazione. Ottima posizione per raggiungere in modo pratico e veloce i maggiori luoghi di attrazione, San Gimignano, Siena , Firenze, Colle di Val d' Elsa

4.93 out of 5 average rating, 119 reviews

Condo in San Gimignano

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.

4.87 out of 5 average rating, 181 reviews

Casa Luce Modern Urban Chic Apartment in Tuscany

Enjoy Tuscany in our cozy cute apartment, very conveniently located between Florence and Siena and ideal if you want to explore the countryside. The neighborhood is quiet with free parking outside the building. There is a market store, bar, butcher, beauty salon, and cafes all nearby walking distance. Also you can come to visit our organic farm and get fresh veggies, fruit and eggs you can cook at home. Smoking is allowed only on the balcony.

4.91 out of 5 average rating, 324 reviews

Apartment 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

4.69 out of 5 average rating, 222 reviews

Apartment in Poggibonsi direction San Gimignano

Apartment on the first floor in the center, in an old building. , Double bed and Spacious double sofa bed (190x160) , Free parking starting from 100 m , Discount (Coop 250 meters, Lidl 750 meters, Penny 1.9 km) , easily reachable from the station (train-bus). Nearby locations: , San Gimignano (11 km by bus 15 minutes) , Siena (30 km by bus / train 30 minutes) , Volterra (35 km) , Florence (44 km by bus / train 50 minutes)

4.92 out of 5 average rating, 107 reviews

Appartamento accogliente in zona centrale

COMODISSIMO APPARTAMENTO composto da due camere, bagno e soggiorno-cucina con luminoso affaccio su ampia terrazza, situato vicino alla clinica Siena Eye Laser, al centro e ai principali servizi di trasporto, dista infatti circa 600 mt dalla stazione ferroviaria e circa 50 mt dalla fermata del bus. Possibilità di parcheggio gratuito per chi si sposta in auto. Non è consentito fumare all'interno dell'appartamento.

4.89 out of 5 average rating, 254 reviews

Home in Poggibonsi

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).

4.89 out of 5 average rating, 198 reviews

Farm stay in Simignano

Casa al Gianni - Capanna

Ciao, siamo Cristina & Carmelo! Vi invitiamo a vivere un’esperienza autentica nel nostro agriturismo “Casa al Gianni” situato 20 min da Siena. Il nostro marchio è la vita semplice a stretto contatto con la natura e gli animali della nostra fattoria. Immerso tra i boschi e la splendida campagna toscana trascorrerai una vacanza indimenticabile. Questo angolo di paradiso ti rimarrà nel cuore!

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 Cipressino

4.94 out of 5 average rating, 64 reviews

Casa Sornano - apartment with a view over Chianti

SabrinaRating, 5 stars3 weeks ago

A comunicação com Gael foi extremamente fácil. Embora ele estivesse fora da cidade, os coanfitriões Angelo e Alessandro foram super cordiais e atenciosos. Realmente nos sentimos em casa. Voltaríamos 1 milhão de vezes, com certeza!!!

4.98 out of 5 average rating, 228 reviews

Condo in Poggibonsi

Casa Amaryllis

GiuliaRating, 5 stars1 week ago

Tutto impeccabile! Proprietaria estremamente gentile e disponibile: ha anticipato il check-in di qualche ora e ci ha permesso di rimanere oltre l’orario di check-out. Ci ha accolti davanti all’appartamento, mostrandoci casa e dandoci ottimi consigli anche per visitare la zona. La casa era pulitissima, in cucina non mancava nulla: da utensili, piatti, olio, sale, caffe..disponeva di ogni cosa! Appartamento spazio, balcone grande e molto accogliente! Consiglierò questa soluzione a tutti quelli che passeranno per Poggibonsi!

Villa in Tavarnelle Val di Pesa

4.93 out of 5 average rating, 148 reviews

PODERE GUIDI

TerryRating, 5 stars2 weeks ago

Giuliani is a wonderful host who made us feel as if this slice of paradise was our home, too. The location, the meticulously restored home, the views all make for the ultimate Tuscan experience. But Giuliani and her husband bring it all together with their warmth and attentiveness. It was a tough place to say goodbye to — for now. If you are looking for a Tuscan experience, this is it. And remember to ask for the hosts’ home-cooked meal. It is a culinary experience in the very best sense.

Holiday home in Barberino Val d'Elsa

4.87 out of 5 average rating, 114 reviews

Linearis apt B (4+2) Toscana

BhuwanRating, 5 stars2 weeks ago

Absolutely loved Katia’s place… very nicely kept with very nice touches to the furnishing. She was available all the time. Checked us in and gave us a tour of the property.. had kept her house wine and olive oil for us to try. The property is very beautiful and is close to the nearby village of Poggibonsi which had everything you needed.

Apartment in Tavarnelle Val di Pesa

4.92 out of 5 average rating, 95 reviews

Romantic Apt in the heart of Chianti (with Tennis)

JuleRating, 5 stars1 month ago

Marco ist ein super freundlicher und herzlicher Gastgeber, der viele Sprache (u.a. Deutsch) spricht. Die Kommunikation mit ihm war super. Das Preis-Leistungs-Verhältnis der Unterkunft ist hervorragend. Die Einrichtung ist schon etwas in die Jahre gekommen (zum Beispiel das Bett), aber es ist alles vorhanden, was man benötigt und der Ausblick ist traumhaft. Die Lage der Unterkunft ist perfekt, wenn man in der Toskana viele Ausflüge machen möchte. Wir können diese Unterkunft sehr empfehlen!

Condo in Colle di Val d'Elsa

4.98 out of 5 average rating, 181 reviews

DorminColle - Appartamento in stile toscano

StefanRating, 5 stars4 days ago

Es war ein sehr ❤️licher Empfang und wir konnten sogar früher einchecken ,was bei diesen Temperaturen und der langen Anreise sehr,sehr zuvorkommend war ; mille Grazie!! Monica hatte tolle Ideen für Unternehmungen und es wurde immer schnell und informativ geantwortet.Die Wohnung war Top ausgestattet, zum Glück mit Wasserspender denn die Wohnung liegt im oberen Stock. Bäcker Fußläufig, Supermarkt ebenso.

Holiday home in Poggibonsi

4.83 out of 5 average rating, 41 reviews

Podere Chiocciola, appartamento con 2 camere

GLORIARating, 5 stars9 months ago

Para disfrutar en familia y compartir recorriendo los pueblos cerca recomendamos esta casa pues todo es impecable en aseo y siempre tienen una sonrisa .