Holiday rentals in Chientina

Casa al Gianni - The Simignano Barn

Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and al fresco dinners. A memorable getaway awaits you in this little slice of paradise!

Tuscan House with Private Jacuzzi in Chianti

An oasis of peace in the heart of Tuscany, along the wine route! - Exclusive Jacuzzi in your own private garden - Strategic location between the medieval towns of Certaldo, San Gimignano, Siena, and Florence - A 700 sqm private garden filled with the sweet sound of birds singing - A newly renovated home where history meets modern comfort and unique design - The warmth of a wood-burning fireplace to heat your beautiful winter dreams - The perfect place to regenerate and completely unplug

Charming apartment with garden, pool and valley view

Apartment in Historical building with shared garden and pool. The property is located in a typical Medieval Tuscan village close to Terricciola (PI) which is part of the wine route. The historic palazzo was built in the 17th Century and has been converted into several individual apartments sharing a private swimming pool and a garden. This lovely apartment has a private car parking and a stunning view over the hills. The village is only 25 min. from Pisa Airport and 35 min. from the coast.

Casa Billi

Cozy 90-square-meter apartment with a beautiful view of the countryside on the second and top floors (no elevator) of a recently renovated old building. Two double bedrooms, a living room with a kitchen, a study, two bathrooms, one with a shower, and a storage room. Exclusive use of a beautiful terrace (not on the apartment floor). A few minutes' walk and you will be in the center of the lively village of Palaia, where you will find small shops for shopping, restaurants, pubs and a bar.

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Luxury Medieval Tower • Exclusive Chianti Stay

Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

House with a breathless view in Tuscany

Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

Live the Tuscany Experience in Our Country House

An amazing experience between nature, flavor and relax in the heart of Chianti. Situated between Barberino Tavarnelle, San Gimignano, Greve in Chianti, and Florence, Belvedere 27/A overlooks the Santa Maria Novella Castle, amidst olive groves and vineyards with an amazing view. A countryside Tuscan home, surrounded by greenery and olive’s fields, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a relaxing and peaceful holiday.

Tuscan Luxury Villa • Natural Pool & Privacy

Immagina di svegliarti in totale privacy, circondato dalle colline del Chianti, con la tua piscina naturale, la spiaggia e il chiringuito. Non è solo un soggiorno, ma una vera “private luxury experience” toscana. Tenuta Virgilio nel Chianti è una villa immersa nella natura, perfetta per chi cerca relax, silenzio ed esclusività in Toscana. Oltre 3 ettari di uliveto e totale privacy: nessuno spazio condiviso, solo la tua esperienza in Toscana.

"Quercia" Glamping Tent with Jacuzzi

The beautiful setting of this romantic place surrounded by nature will leave you speechless. In the most scenic area of the property, there is a beautiful 50-square-meter Glamping structure with a double bedroom, bathroom, kitchen and a beautiful terrace overlooking the entire hill. The property was created for couples who want to spend unforgettable moments in tranquility and surrounded by nature, but with all the comforts.

Countryside Dream farm in Tuscany

Have you ever dreamed of experiencing the rolling hills of Tuacany ? This is a berautiful organic farm in the middle of Tuscan Hills, you will be surrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.