Family-friendly vacation rentals in Certaldo

Historic house in heart of Tuscany

The apartment is located in a ex-benedectine abbay along the famous Via Francigena. Inside, there are some furniture of the XVIII century and orginal frescoes. There are all confort to make pleasant your holiday: three double bedrooms, a kitchen, a bright living room, a bathroom with shower and a small closet. It’s in the middle of the Tuscan hills, a few kilometers from San Gimignano’s towers and from the medieval country of Certaldo Alto. You can easily reach Siena, Florence, Volterra, Monteriggioni and the picturesque countryside of Chianti.

Ancient 17th-century farmhouse in Chianti, Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing exclusive services and experiences tailored to you. 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 swimming pool with a relaxation area on a panoramic terrace, with wonderful views of the castle, hills, and vineyards and breathtaking sunsets.

Casa al Gianni - Oak

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism property in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds, and the warmth of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a vacation; it’s a return to our roots. This peaceful haven will stay in your soul. We look forward to welcoming you!

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

Stone House with Exclusive Pool Codilungo in Chianti

Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

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.

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

In the center of Certaldo

The apartment is located in the heart of Certaldo, a small and quiet town nestled among the unmistakable Tuscan hills, just a 5-minute walk away you will find the train station from where you can reach Siena or Florence, and also other cities, or by car. Certaldo has a unique medieval charm: the historic center in the upper part is in fact beautifully preserved and from our apartment you can reach it on foot in a few minutes or with a panoramic funicular.

Nada Home

3 comfortable, fully air-conditioned double bedrooms, each with its own private bathroom, in the heart of Chianti, ideally located between Florence, Siena and San Gimignano. A welcoming, well-kept home in the peaceful Tuscan countryside. Fully equipped kitchen with dishwasher, oven and bar area, plus a laundry room with washing machine and dryer. Private garden for your exclusive use with a private hydromassage pool, heated in winter upon request 🌷

Villa Isabella

Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

Tenuta di Pomine Certaldo (FI) Papavero Apartment

Three-room apartment 65 m2 on the first floor. Tasteful furnishings: 1 double bedroom, 1 bedroom with two beds, kitchen (4 hotplates), oven, refrigerator, freezer, dishwasher, microwave, TV, Wi-Fi. Bathroom with shower, sink, bidet, toilet. Beautiful panoramic views of the countryside. Linen change/week. Accommodation tax of €2 per day per person to be paid upon arrival for the first 6 days (from 14 years of age)

Cercis - La Palmierina

The apartment is part of a completely fenced estate of 60 hectares of unspoiled nature: more than 1000 olive trees, countless cypresses and fragrant forests create an idyllic environment for those seeking tranquility and silence. The Palmierina estate is near Castelfalfi (a true jewel of medieval architecture) and close to Florence (50 Km), Siena (50 Km), and Pisa (50 Km). There are two golf courses nearby.