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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 £67 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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Guest favourite
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

4.88 out of 5 average rating, 338 reviews
Top guest favourite
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.
Apartment in Noce

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . 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 vista su castello e vigneti con tramonti unici.

5.0 out of 5 average rating, 350 reviews
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

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.

4.98 out of 5 average rating, 136 reviews
Top guest favourite
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.
Home in Montespertoli

Sunny Beauty

Tranquillità - Bellezza - Relax. Siamo nel Chianti, San Gimignano, Firenze, Siena, Volterra e Pisa non sono lontane. Bellezza e cose straordinarie ci circondano, nonché buon cibo genuino, soprattutto ottimo vino e ottimo olio. Casa completamente ristrutturata. Nota: Ci potete trovare su Google maps. Negozi chiudano alle 20.00 Sono una guida turistica del territorio, ho studiato Arte e canto. Vi auguro un buon soggiorno a casa mia, arredata con amore e col obiettivo di farvi stare bene.

4.85 out of 5 average rating, 213 reviews
Guest favourite
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

Vacanza immersa nella campagna Toscana 'Canaiolo'

"💖Regalati una vacanza immersa nella campagna Toscana, con grande piscina attrezzata 🌞💐I profumi della natura, i paesaggi mozzafiato e la piscina saranno la cornice per il relax che cerchi. 🚴🏻‍♂️🏃‍♀️Poi se senti il bisogno di muoverti puoi nuotare, camminare o correre tra i sentieri intorno alla tua casa in campagna. 🏛La posizione strategica dell'appartamento consente di fare escursioni a Firenze, Siena e Pisa. ✨Gli appartamenti sono di recente ristrutturazione in stile toscano."

4.87 out of 5 average rating, 118 reviews
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

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!

4.92 out of 5 average rating, 146 reviews
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

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.

4.98 out of 5 average rating, 105 reviews
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

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

4.84 out of 5 average rating, 148 reviews
Top guest favourite
A panoramic view captures a hillside town featuring a historic tower, surrounded by lush greenery and rolling vineyards. The landscape displays a blend of trees, fields, and distant hills under a clear sky, showcasing the natural beauty of the Tuscan countryside.
Holiday home in Montespertoli

Chianti Panorama | House with 3 En-Suite Bathrooms

Immerse yourself in the authentic magic of Chianti 🍷 in our exclusive country home 🏡, boasting panoramic views over Montespertoli and its rolling hills . Strategically located just 1 km from the town center and main amenities 🛍️ like cafes ☕, restaurants 🍽️, and supermarkets 🛒, it is within easy reach of Florence , San Gimignano , Volterra and Siena . All the wonders of Tuscany will be just a charming day trip away!

4.95 out of 5 average rating, 146 reviews
Guest favourite
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

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.

4.91 out of 5 average rating, 126 reviews
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

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).

4.95 out of 5 average rating, 219 reviews
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

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.

4.77 out of 5 average rating, 233 reviews

Popular amenities for Montespertoli family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano

Casa al Gianni - Il Fienile di Simignano

4.97 out of 5 average rating, 194 reviews
Top guest favourite
Farm stay in Greve in Chianti

Agriturismo nel Chianti con Piscina

4.99 out of 5 average rating, 510 reviews
Superhost
Home in Barberino Tavarnelle

La Casa di Nada Home

4.87 out of 5 average rating, 215 reviews
Top guest favourite
A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.
Tower in Fiesole

A Big Dream in a Little Tower.

4.95 out of 5 average rating, 219 reviews
Top guest favourite
A heated jacuzzi is situated under a shaded pergola, surrounded by lush greenery and colorful flowers. The serene outdoor space is complemented by a gravel path leading towards vineyards in the background, inviting relaxation and privacy.
Villa in San Casciano In Val di Pesa

Il Vichiaccio: Florence Villa with Jacuzzi

4.95 out of 5 average rating, 202 reviews
Top guest favourite
The jacuzzi is featured outdoors, illuminated with blue lights, creating a calming atmosphere at night. The surrounding stone walls provide privacy, and a dining table can be seen nearby. Steam rises, indicating the water is warm and inviting.
Cottage in San Casciano In Val di Pesa

Il Fienile, Cottage in the country with Jacuzzi

4.96 out of 5 average rating, 194 reviews
Top guest favourite
A tranquil pool area is highlighted by a clear blue pool flanked by sun loungers under white umbrellas. Lush greenery surrounds the property, with a charming farmhouse visible in the background, and inviting pathways guide guests through the scenic landscape.
Villa in Capannori

Farmhouse , pool, 13 px. Lucca 10km

4.99 out of 5 average rating, 148 reviews
Guest favourite
Home in Barberino Tavarnelle

SuiteLouise.pool, Hot Tub,homeGym & private Garden

4.91 out of 5 average rating, 124 reviews

Family- and pet-friendly home rentals

Top guest favourite
The cottage is positioned amidst a lush garden, featuring a stone pathway leading to the entrance. A rustic facade is complemented by wooden benches and white outdoor furniture, surrounded by trees and greenery that provide a serene rural backdrop.
Cabin in Montespertoli

The little house in the garden

4.95 out of 5 average rating, 166 reviews
Top guest favourite
A well-maintained garden features a green lawn surrounded by olive trees. Colorful flower pots with red blooms accent the space. A shaded seating area under a canopy provides a cozy spot for relaxation, with additional garden ornaments and a path leading through the landscape.
Cottage in Montespertoli

Casa del Sole nel Chianti

4.91 out of 5 average rating, 141 reviews
Superhost
A spacious living area is divided into a seating section with a patterned sofa and coffee table, and a dining area featuring a wooden table surrounded by chairs. Light floods in through a large window with cream curtains, illuminating the neutral-colored walls and rustic terracotta tiles.
Farm stay in Montespertoli

Agriturismo Lucciano "Cipresso"

4.77 out of 5 average rating, 108 reviews
Top guest favourite
A sunlit pool area features a spacious salt-water pool with a surrounding deck. Several lounge chairs are arranged with umbrellas, providing shaded seating. A rustic stone building serves as a backdrop, displaying traditional Italian architectural elements and large windows that invite natural light.
Villa in Orentano

Villa Gourmet Food, Pizza, Chef, Pool and Nature

4.98 out of 5 average rating, 126 reviews
Guest favourite
A serene pool area is highlighted by lounge chairs set along a stone terrace. The water reflects a golden sunset, providing a tranquil atmosphere. Surrounding greenery adds to the natural beauty, creating a peaceful environment for relaxation.
Flat in La Presura

Countryhouse 9 kms to Florence-3+2,free park, wine

4.86 out of 5 average rating, 275 reviews
Superhost
A tranquil pool area is surrounded by lush greenery, featuring a clear blue swimming pool with a light stone border. Three lounge chairs are positioned by the poolside, inviting relaxation while enjoying the serene landscape.
Flat in Montespertoli

Tuscan relax appartment with private pool

4.88 out of 5 average rating, 187 reviews
Top guest favourite
Bright seating area features two white armchairs and a patterned ottoman, surrounded by large glass arches that open to a lush garden. Natural light floods the space, enhancing the exposed stone walls and wooden ceiling beams, complemented by a large potted plant.
Villa in San Casciano in Val di Pesa

Luxury Villa in the very heart of Chianti

4.97 out of 5 average rating, 119 reviews
Guest favourite
The historic tower apartment, part of a small castle, is surrounded by lush greenery and trees. The building features multiple windows, showcasing traditional architectural elements. A picturesque garden with low shrubs and budding flowers provides a tranquil atmosphere, inviting exploration of the outdoor space.
Castle in Bagno A Ripoli

TOWER apartment in small castle near Florence

4.92 out of 5 average rating, 569 reviews

Family-friendly home rentals with a pool

Top guest favourite
Home in Greve in Chianti

Relax e charme tra le colline del chianti

4.99 out of 5 average rating, 113 reviews
Top guest favourite
A modern swimming pool is surrounded by a spacious wooden deck, lined with lounge chairs, offering expansive views of the rolling hills and olive groves. A large tree provides shade next to the pool, creating a serene outdoor space for relaxation.
Farm stay in Lastra a Signa

Authentic Farmhouse Apartment

4.98 out of 5 average rating, 117 reviews
Top guest favourite
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

Cercis - La Palmierina

4.96 out of 5 average rating, 145 reviews
Top guest favourite
A serene outdoor view features olive trees dotting a grassy area. A few lounge chairs are arranged by the pool, which reflects the soft hues of early morning light. A mist envelops the landscape, enhancing the tranquil setting.
Farm stay in Lastra a Signa

Flat for 4 with garden & pool in agriturismo

4.99 out of 5 average rating, 169 reviews
Top guest favourite
A well-maintained garden surrounds a refreshing pool, bordered by manicured grass. A comfortable seating area, featuring two lounger chairs and a shaded umbrella, provides a serene spot for relaxation. Soft greenery and flowering shrubs form a natural backdrop, enhancing the tranquil atmosphere.
Villa in Tignano

Villa Isabella

4.96 out of 5 average rating, 207 reviews
Top guest favourite
The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.
Cottage in Barberino Tavarnelle

Stone House with Exclusive Pool Codilungo in Chianti

4.98 out of 5 average rating, 217 reviews
Top guest favourite
A charming outdoor dining area features a wrought-iron table adorned with glasses and a bottle of champagne. Fresh strawberries and colorful sprinkles are placed on the table, surrounded by vibrant flowers in pots, creating a welcoming space for relaxation and enjoyment.
Home in Malmantile

La casetta dell'Ines

5.0 out of 5 average rating, 109 reviews
Top guest favourite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle in Ferrano

Il Castello di Ferrano - Castle in Tuscany

4.99 out of 5 average rating, 226 reviews

Destinations to explore