Vacation rentals in Pignano

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, 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, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

Relaxation and charm in the Chianti hills

Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient family-run property from the 1600s located in the beautiful hills of Chianti in Tuscany, with the possibility of arranging a private shuttle and local experiences directly with our family. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with incomparable sunsets.

Florence Sunset Hills • Giogoli

Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Exclusive Tuscan Villa with private pool

Amazing exclusive authentic big villa, real Tuscan style, air condition. 15 guests. 6 double bedrooms and 1 triple rooms. Bright dining room, fully equipped kitchen. Private pool (15x7mt). The area is really quiet and super relaxing. You will enjoy a stunning view over the characteristic tuscan countryside. About 15 minutes drive from San Gimignano, the most famous medieval village just between Florence and Siena. Wifi, private parking area!! The best place for trekking and outdoor sport lovers!

Torre dei Belforti

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Private Courtyard | 3BR/3BA | Garage

Welcome to Casa Costarella.<br><br>Wake up in San Gimignano’s historic center and step into your own private courtyard — a rare feature within the city walls.<br><br>This 120 m² / 1,290 sqft residence spans two levels and blends preserved historic character with modern comfort.<br><br>☞ Enclosed private courtyard<br>☞ 3 bedrooms / 3 full bathrooms<br>☞ Free covered garage for 1 car (5-minute walk)<br>☞ Underfloor heating & cooling<br>☞ High-speed Wi-Fi<br>☞ Self check-in<br><br>

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.

Luxury Medieval Tower • Exclusive Chianti Stay

Welcome to one of the most exclusive residences in Chianti: a medieval tower transformed into a refined luxury retreat overlooking the Tuscan hills. Contemporary design, iconic furnishings, works of art and luxury comforts come together in a unique experience. An oasis of tranquility with a private garden, glass annex, Wi-Fi, and smart working area. Extra services: private chef, tastings in the cellar, wellness treatments and tours of the most beautiful villages in Tuscany.

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.”

Il Castro Luxury San Gimignano. Michelangelo Suite

Il Castro is a group of apartments finely recovered from a careful renovation, which has left the signs of the past unchanged. The classic furnishings, meticulously decorated by local artisans, blend in perfect harmony with elements of fine design, giving a minimalist and refined effect. The finishes of the bathrooms are extraordinary, where the search for detail and the quality of the materials transform the environment into something unique.

Romantic Villa with private pool - "Il Pollaio"

Il Pollaio is a traditional, charming Tuscan stone house with a warm, relaxed atmosphere, surrounded by the peace and quiet of the countryside. With air conditioning, a private pool nestled in the greenery and a fully fenced property. Extra services on request: private chef and housekeeping every other day. Ideally located, yet secluded and private. Ample parking. PLEASE NOTE: Read the details under “Show more” in “Other things to note”