Family-friendly holiday rentals in Montespertoli

Holiday home in loc. Simignano

A charming rustic farmhouse is set against a dramatic sky, framed by lush green trees. The exterior features warm-toned walls and a tiled roof, while a spacious yard includes seating arrangements for outdoor relaxation, inviting guests to enjoy the serene countryside.

4.93 out of 5 average rating, 241 reviews

Casa al Gianni - Oak

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to ‘Casa al Gianni’, our farm stay 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 companionship of our animals. It’s an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a holiday; it’s a return to our roots. This haven of peace will stay with you in your heart. We look forward to welcoming you!

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5.0 out of 5 average rating, 218 reviews

An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.

Condo in Noce

Ancient Podere of the 1600s in Chianti in Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful Chianti hills in Tuscany, with the possibility of organising 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 will find a saltwater swimming pool with a relaxation area on a panoramic terrace with a wonderful view of the castle, hills and vineyards, with breathtaking sunsets.

KitchenFamilyWalkability

4.99 out of 5 average rating, 112 reviews

Home in Greve in Chianti

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.

FamilyIndoor spacesSleep quality

4.88 out of 5 average rating, 338 reviews

Townhouse in Scandicci

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

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Guest suite in Montespertoli

The entrance features a sturdy door with a reflective surface, framed by a rustic stone wall and accented by a decorative lantern. A window with iron bars contains flower pots, contributing to the charming exterior of the villa.

4.98 out of 5 average rating, 136 reviews

Villa i Lecci 1

At Villa i Lecci you will have an accommodation for exclusive use, surrounded by the beautiful Chianti landscape, just 1.8 km from the town center. The two double bedrooms, cozy and spacious, are connected by a corridor to the living room with fireplace and to the dining room with kitchen. Perfect for a relaxing pool vacation or a tour of Chianti and the main Tuscan cities, Florence, Siena, Pisa, San Gimignano and Volterra. Suitable for couples, families, and groups of friends.

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Guest favourite

A dining area is illuminated by natural light pouring through an open window. A wooden table is set for four, surrounded by white chairs. Scenic hills are visible through the window, enhancing the inviting atmosphere of the space.

Apartment in Montespertoli

4.92 out of 5 average rating, 144 reviews

La Chicchera, ground floor apt with panoramic view

La Chicchera is an apartment recently renovated and cared for in every detail in a very quiet street in the centre of Montespertoli, a village in the heart of Chianti and a short distance from Florence and all the other cities of art in Tuscany. Mini-markets, bars, pharmacies, restaurants, shops, banks are within easy walking distance; bus stops are also within walking distance. We look forward to welcoming you and being part of your stay in Tuscany with tips and tricks!

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A scenic view unfolds from a terrace adorned with vibrant flower pots. Lush greenery and rolling hills stretch into the distance, framed by trees. The clear blue sky complements the picturesque landscape of vineyards and fields, creating a serene outdoor setting.

4.85 out of 5 average rating, 213 reviews

Sunny Beauty

Tranquility - Beauty - Relaxation. We are in Chianti, San Gimignano, Florence, Siena, Volterra and Pisa are not far away. Beauty and extraordinary things surround us, as well as good genuine food, especially great wine and great oil. Fully renovated home. Note: You can find us on Google Maps. Shops close at 8:00 p.m. I am a local tour guide, I studied art and singing. I wish you a pleasant stay in my home, furnished with love and with the aim of making you feel good.

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Villa in Barberino Tavarnelle

A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.

4.98 out of 5 average rating, 104 reviews

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.

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Guest favourite

A charming house is framed by lush greenery, with several trees dotting the manicured lawn. The exterior features warm tones, complemented by a covered porch area. Various plants provide a natural ambiance, enhancing the serene outdoor space.

4.84 out of 5 average rating, 148 reviews

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

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4.95 out of 5 average rating, 218 reviews

A well-kept garden features neatly trimmed grass and a variety of trees, including tall pines, providing shade and a natural atmosphere. A subtle hammock is visible between two trees, inviting relaxation in the serene outdoor space.

Villa in Montespertoli

Farmhouse in Chianti

Beautiful portion of a farmhouse immersed in Chianti with a beautiful swimming pool, surrounded by vineyards and olive trees, perfectly furnished with a large garden and parking spaces. It is located 20 minutes from Florence, 40 from Siena and 50 from Pisa, in a few minutes you can reach Certaldo (birthplace of Boccaccio) and Vinci (birthplace of Leonardo Da Vinci). The house is halfway between Montespertoli and San Casciano (7km).

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An aerial view captures a rustic countryside villa nestled within lush greenery and olive groves. The structure features a tiled roof and surrounded by trees, with a separate building visible nearby. The serene landscape enhances the sense of privacy and tranquility.

4.91 out of 5 average rating, 126 reviews

Costalmandorlo, a rustic home in the heart of Tuscany

Costalmandorlo is your peaceful corner in the center of Tuscany. A charming country cottage restored and furnished with care and with a style that combines ancient and modern. Here you can slow down and relax surrounded by the sounds of nature, admiring beautiful sunsets and having long breakfasts in the garden. A short distance between Florence, Siena and Pisa, it is an excellent base for touring Tuscany.

KitchenFamilyWalkability

An outdoor terrace is shown with a dining table set for meals. Comfortable chairs surround the table, and vibrant plants add greenery. The expansive view of rolling hills under a clear blue sky is prominently featured, providing a serene backdrop.