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.

Indoor spaces · Kitchen · Pets

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!

Kitchen · Indoor spaces · Grill

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.

Indoor spaces · Family · Location

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.

Kitchen · Family · EV charging

Cosy Tuscan Home near Florence & San Gimignano

A COZY NEST where tradition and modern comfort meet. Perfect for those who want to slow down, relax, and experience the most authentic Tuscany, away from the hustle and bustle. Imagine waking up in the heart of a Tuscan village, looking out over the square, and starting the day in harmony with the local tranquility and rhythms. The apartment, completely renovated and tastefully furnished, is located in the historic center of Gambassi Terme, a strategic location for exploring the wonders of Tuscany.

Family · Indoor spaces · Laundry

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.

Kitchen · Indoor spaces · Pool

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.

Family · Indoor spaces · Long stay

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.

Family · Kitchen · Value

I Limoni Apartment in Tuscany

In the Chianti hills between Florence Siena rich in history and evocative natural sceneries, the cradle of civilizations that have left an artistic and cultural heritage of unparalleled value, surrounded by unspoiled nature luxuriant vineyards cultivated as gardens, centuries-old olive groves, imposing cypresses, is the "VillaBassa" farm is located. easily accessible Florence 30 min Pisa 50 min Siena 50 min S.Gimignano 30 min Monteriggioni 45 min

Kitchen · Family · Shared spaces

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 🌷

Family · Kitchen · Hot tub

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)

Family · Indoor spaces · Location

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.

Kitchen · Indoor spaces · Check-in