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Family-friendly holiday rentals in Montespertoli

Find and book unique family-friendly homes on Airbnb

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

  • Total holiday rentals

    Explore 20 holiday rentals in Montespertoli

  • Nightly prices starting at

    Montespertoli holiday rentals start at $115 SGD per night before taxes and fees

  • Verified guest reviews

    Over 980 verified reviews to help you choose

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Montespertoli holiday rentals include wifi 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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Superhost
Townhouse in Scandicci
4.88 out of 5 average rating, 338 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

Top guest favourite
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.
Apartment in Noce
5.0 out of 5 average rating, 218 reviews

Antico Podere del 1600 nel Chianti in Toscana

Podere Vergianoni è un antica e storica proprietà risalente al 1600 situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare servizi ed esperienze esclusive su misura per voi . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con stupenda vista su castello colline e vigneti con tramonti mozzafiato.

Top guest favourite
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, 136 reviews

Villa i Lecci 1

A Villa i Lecci avrete a disposizione un alloggio ad uso esclusivo, circondato dallo splendido paesaggio del Chianti, a soli 1,8 km dal centro del paese. Le due camere doppie, accoglienti e spaziose, sono collegate da un corridoio al salotto con camino e alla sala da pranzo con cucina. Perfetto per una vacanza rilassante a bordo piscina o per un tour del Chianti e delle principali città toscane, Firenze, Siena, Pisa, San Gimignano e Volterra. Adatto a coppie, a famiglie e a gruppi di amici.

Top guest favourite
Home in Greve in Chianti
4.99 out of 5 average rating, 112 reviews

Relax e charme tra le colline del chianti

Bellissima colonica in pietra, indipendente, immersa tra gli olivi e le colline del Chianti, con giardino privato e piscina panoramica. Piano terra con ampi saloni, antico camino e forno a legna, soggiorno luminoso e cucina full optional. Al primo piano tre suites composte da camera, studio e bagno privato. Accesso tramite cancello e strada bianca in proprietà privata a soli 500 metri dal paese di Strada in Chianti. Ideale per quiete e relax. Location strategica per visitare la Toscana.

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.
Flat in Montespertoli
4.92 out of 5 average rating, 144 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 favourite
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.
Villa in Barberino Tavarnelle
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.

Top guest favourite
A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 429 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

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.
Home in Montespertoli
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

Superhost
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, rustico nel cuore della Toscana

Costalmandorlo è il tuo angolo di pace al centro della Toscana. Un affascinante casolare di campagna restaurato e arredato con cura e con uno stile che concilia antico e moderno. Qui potrete rallentare e rilassarvi circondati dai suoni della natura, ammirando splendidi tramonti e facendo lunghe colazioni in giardino. A poca distanza tra Firenze, Siena e Pisa, è un'ottima base per fare il tour della Toscana.

Top guest favourite
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, 218 reviews

Colonica nel Chianti

Splendida porzione di casa colonica immersa nel Chianti con bellissima piscina, circondata da vigne e olivi, perfettamente arredata con vasto giardino e posti macchina. Si trova a 20 minuti da Firenze, 40 da Siena e 50 da Pisa, in pochi minuti si raggiunge Certaldo (città natale di Boccaccio) e Vinci (città natale di Leonardo Da Vinci). la casa è a metà strada tra Montespertoli e San Casciano (7km).

Superhost
A bright kitchen area features a dining table surrounded by five white chairs and a sofa constructed from pallets. A bowl of fruit sits at the center of the table. The walls are painted a warm yellow, complemented by rustic shelving displaying wine bottles and books.
Apartment in Montespertoli
4.77 out of 5 average rating, 233 reviews

Appartamento "Bellaria"

Bellaria é situato sulla strada principale che collega il paese ( 10minuti a piedi ) ai vari punti di interesse. Adatto come base di appoggio per visitare la Toscana. ●Tassa di soggiorno da pagare in contanti al check-in 1,50€ a notte per adulto (oltre 14 anni). ●Possibilità di effettuare self check-in con cassetta di sicurezza per le chiavi.

Superhost
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.
Home in Montespertoli
4.92 out of 5 average rating, 105 reviews

Terrazza paradiso nel Chianti tra Firenze e Siena

Svegliati con la vista sulle colline del Chianti, fai colazione sulla terrazza e raggiungi Firenze, San Gimignano e Siena in meno di un'ora. Infine goditi un aperitivo al tramonto. Una casa tranquilla pensata per famiglie e amici che vogliono vivere la Toscana autentica e godersi la pace della campagna senza essere isolati.

Popular amenities for Montespertoli family-friendly rentals