Vacation rentals in Cipressino

4.98 out of 5 average rating, 440 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!

Farm stay in San Gimignano

4.86 out of 5 average rating, 134 reviews

Ulivo double room in San Gimignano, countryside

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

Vacation 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.

Condo in Colle di Val d'Elsa

4.98 out of 5 average rating, 180 reviews

DorminColle - Tuscan-style apartment

Appartamento luminoso e spazioso, composto da confortevole camera matrimoniale con tv, condizionatore portatile, con al suo interno bagno completo di doccia e servizi igienici. Terzo posto letto situato in caratteristica area soppalcata con travi in legno dotato di letto. Ampia cucina dotata di lavastoviglie, macchina del caffè, microonde, erogatore acqua filtrata, Salone con tv e divano, sala da pranzo con vista sul Borgo Antico. Parcheggio gratuito a 150 mt visibile dell’appartamento.

4.96 out of 5 average rating, 238 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.

4.93 out of 5 average rating, 118 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.

4.69 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)

4.89 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).

4.96 out of 5 average rating, 249 reviews

Condo in Panzano

Apt. Panzanello-Panzano in Chianti

The apartment offers all the comforts and tranquility of the Tuscan countryside. Enjoy the wonderful view that you can admire from your private terrace, a perfect place to spend peaceful and serene moments accompanied by a good glass of Panzanello wine. Access to the apartment is private and free parking is available. The kitchen is equipped with everything you need to prepare delicious meals.

4.92 out of 5 average rating, 106 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.

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Other great vacation rentals in Cipressino

4.93 out of 5 average rating, 40 reviews

Home in Poggibonsi

[Chianti]LOFT Garden free parking to San Gimignano

LucaRating, 5 stars1 month ago

Giulia was very available for the check-in time, already on site as soon as we arrived. She showed us the apartment and gave us some tips. She was very helpful in changing the blanket right away when we let her know we were warm at night. Apartment as shown in the photo. I recommend it as a foothold; we are chosen to do an operation in the eyes of the Poggibonsi clinic, a 5-minute drive away. In the following days we moved comfortably to San Giminiano, Certaldo, Siena, Monteriggioni and Florence.

4.97 out of 5 average rating, 96 reviews

Cozy apartment to explore Tuscany

AnnegretRating, 5 stars1 month ago

Everything about Stefano’s apartment was first rate. Clean, comfortable, well equipped in a great location. Easy to walk to great restaurants and supermarket, and explore old town Poggibonsi. Easy, walkable access to train and but to explore fabulous towns further afield. Great undercover parking, easy check in and out, and a great host….friendly, responsive and good local recommendations. Good value for money stay…an all round winner.

4.93 out of 5 average rating, 60 reviews

Condo in Poggibonsi

Casa Yuri a Poggibonsi

TravisRating, 5 stars2 weeks ago

56 steps. That’s the only negative. If you are ok with that, this is a beautiful well apportioned apartment for a great price. If it were 2 floors lower it would probably rent for 2x as much. We were able to find street parking just a few minutes away without much trouble. Comfortable beds. Many dining options close by. Air conditioner actually got the bedroom too cold, I had to turn it down. Large apartment. Cute area. I would stay here again. Great place!

5 out of 5 average rating, 116 reviews

Villa Mocarello "IL LECCIO"

SallyRating, 5 stars1 month ago

Best place to stay!!! The charm of property draws you in immediately! A lovely garden, fresh flowers in the apartment, stunning views of San Gimignano. We loved the touches of old Italy everywhere (with the subtle inclusion of modern flair). And the little extras - a beautiful homemade tart welcomed us, as well as fresh fruit, juices, coffee and creamers and a few more fun surprises! Fabio and Alessandra are fabulous hosts - always answering any of our questions and having excellent advice on where to eat and things to do! The location is perfect for day trips to many of the Tuscan and Chianti region towns. And so lovely to come back to the charm of Fabio and Alessandra’s place. Grazie mille!!!

Home in Barberino Tavarnelle

4.97 out of 5 average rating, 71 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

MeganRating, 5 stars2 weeks ago

How can we even put into words what an incredible experience this was! Antonella was kind and helpful, and her home is just stunning. She made us feel so at home even with our limited Italian. She prepared us a home cooked, four-course meal one night and it was absolutely delicious. She even gave us the leftovers so we could have them for breakfast the next day. The villa was breathtaking and in a perfect location to visit beautiful towns in Tuscany like Pienza, Montepulciano and San Gimignano. We especially loved the pool and visiting with the animals. This was a bucket list stay for us and worth every penny!

Vacation home in Barberino Val d'Elsa

4.87 out of 5 average rating, 113 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.

4.97 out of 5 average rating, 33 reviews

Apartment in Tuscany with giant oak tree

MirandaRating, 5 stars2 weeks ago

Rudi and Lydia are amazing people. Extremely welcoming, helpful and with a broad interest. The yard is beautiful. You reach the house via a strada bianca. The cottage is well and attractively decorated. You have a piece of private garden, but apart from that, you can look everywhere and use it. We had wonderful days and will definitely be back. We have friends with us