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Family-friendly vacation rentals in Montespertoli

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Montespertoli

  • Total vacation rentals

    Explore 20 vacation rentals in Montespertoli

  • Nightly prices starting at

    Montespertoli vacation rentals start at ﺩ.ﺇ 331 per night before taxes and fees

  • Verified guest reviews

    Over 980 verified reviews to help you choose

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Montespertoli vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Montespertoli rentals

  • 4.8 Average rating

    Montespertoli stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Montespertoli

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 343 reviews

Podere Vergianoni immerso nelChianti con piscina

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.

Guest favorite
A large outdoor swimming pool is visible under a clear blue sky, surrounded by lush greenery. The tranquil water reflects the sunlight, creating a calming atmosphere. Vegetation frames the scene, enhancing the privacy of the pool area.
Home in Montespertoli
4.87 out of 5 average rating, 113 reviews

Vacation immersed in the Tuscan countryside 'Canaiolo'

"💖Treat yourself to a vacation immersed in the Tuscan countryside, with a large equipped swimming pool 🌞💐The scents of nature, breathtaking landscapes and the swimming pool will be the setting for the relaxation you seek. 🚴🏻‍♂️🏃‍♀️Then if you feel the need to move, you can swim, walk, or run along the paths around your country home. 🏛The apartment's strategic location allows you to make excursions to Florence, Siena, and Pisa. ✨The apartments have been recently renovated in Tuscan style."

Top guest favorite
Townhouse in Scandicci
4.89 out of 5 average rating, 335 reviews

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

Guest favorite
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, 143 reviews

La Chicchera, ground floor apt with panoramic view

La Chicchera è un appartamento recentemente rinnovato e curato nei minimi dettagli in una via molto tranquilla del centro di Montespertoli, un paesino nel cuore del Chianti e a breve distanza da Firenze e da tutte le altre città d'arte della Toscana. Facilmente raggiungibili a piedi minimarket, bar, farmacie, ristoranti, negozi, banche; a pochi passi anche le fermate dell’autobus. Saremo felici di accogliervi e poter far parte del vostro soggiorno in Toscana con consigli e suggerimenti!

Top guest favorite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5 out of 5 average rating, 226 reviews

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.

Top guest favorite
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.
Guest suite in Montespertoli
4.98 out of 5 average rating, 134 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.

Top guest favorite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.93 out of 5 average rating, 281 reviews

Casa al Gianni - Hut

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Guest favorite
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.
Home in Montespertoli
4.85 out of 5 average rating, 146 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

Top guest favorite
A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.
Home in Montaione
4.96 out of 5 average rating, 139 reviews

Cercis - La Palmierina

E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

Top guest favorite
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
4.95 out of 5 average rating, 216 reviews

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).

Guest favorite
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.
Home in Montespertoli
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.

Top guest favorite
Farm stay in Pisa
4.99 out of 5 average rating, 336 reviews

Tenuta Chiudendone in Tuscany

Great place in the middle of Tuscan Hills, you will be sorrounded 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.

Popular amenities for Montespertoli family-friendly rentals