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Family-friendly holiday rentals in Monticiano

Find and book unique family-friendly homes on Airbnb

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

  • Total holiday rentals

    Explore 40 holiday rentals in Monticiano

  • Nightly prices starting at

    Monticiano holiday rentals start at $70 AUD per night before taxes and fees

  • Verified guest reviews

    Over 880 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Monticiano holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Monticiano rentals

  • 4.8 Average rating

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

Top-rated family-friendly rentals in Monticiano

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

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Top Guest favourite
An aerial view of a rustic complex surrounded by lush greenery. A swimming pool is visible at the center, accompanied by sun loungers. The surrounding landscape features rolling hills and fields, creating a serene atmosphere.
Holiday home in Sovicille

Podere La Castellina - N°4 FICO

Appartamento in pietre e mattoni all'interno del "Podere la Castellina" (ex convento 13° secolo), nel magnifico parco naturale della Montagnola Senese. L'appartamento situato al primo piano può ospitare comodamente 4 persone (2+2 bambini) e comprende: - ampio soggiorno con tv, divano e 2 letti singoli - cucina abitabile con forno - camera matrimoniale - bagno con doccia A disposizione degli ospiti piscina panoramica, solarium e terrazza con vista mozzafiato, dotata di forno a legna e barbecue.

Indoor spacesKitchenComfort

4.96 out of 5 average rating, 110 reviews
Guest favourite
Farm stay in Castelnuovo Berardenga

Apartment in a Tuscan farmhouse at Le Pietre Vive

Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.

FamilyIndoor spacesCleanliness

4.92 out of 5 average rating, 359 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.
Condo 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.

KitchenFamilySleep quality

5.0 out of 5 average rating, 352 reviews
Guest favourite
Home in Asciano

Palazzo Monaci - Piscina nelle crete Senesi

Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

KitchenIndoor spacesParking

4.96 out of 5 average rating, 142 reviews
Guest favourite
A rustic stone farmhouse is nestled in a lush green landscape, surrounded by rolling hills and tall cypress trees. The sun casts a warm glow on the exterior, highlighting the charming architecture. An open courtyard with a small pool can be seen in the foreground.
Farm stay in Campiglia D'orcia

Agriturismo Poggio Bicchieri ap. Memoria

Rilassati con tutta la famiglia in questo alloggio. L’agriturismo si compone di due appartamenti indipendenti con sala, cucina, camera e bagno. Non dovrai condividere nulla con il altri ospiti poiché é stata nostra cura organizzare tutto in maniera che ognuno abbia i propri spazi e tutto sia separato. All'esterno c’é un barbecue, tavolo con sedie e le sdraio. Nelle vicinanze Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino e Bagni San Filippo. Per raggiungerci 1,5 km di strada sterrata!

KitchenFamilyBackyard

4.92 out of 5 average rating, 626 reviews
Guest favourite
A serene outdoor pool area is surrounded by lush greenery and rustic stone pathways. Lounge chairs are positioned beside the pool, creating a space for relaxation. The picturesque villa can be seen in the background, framed by trees and gentle hillside.
Villa in Castiglione d'Orcia

Wp Relais Borgo Vignalunga

Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

Indoor spacesKitchenAccuracy

4.95 out of 5 average rating, 146 reviews
Top Guest favourite
An aerial view showcases a rustic farmhouse surrounded by lush greenery. The property features a terracotta roof, several outdoor areas, and multiple swimming pools nestled among trees, emphasizing the tranquil rural setting.
Farm stay in Murlo

Elegant farmhouse Siena

L'appartamento, di 200 mq, fa parte di una casa colonica del 1600: ospita comodamente 6 persone, ha 3 grandi camere da letto, un salone principesco, una cucina con camino, due bagni e un affaccio mozzafiato sulla campagna toscana fino a Montalcino. Dal 1 Aprile 2025, il comune di Murlo ha istituito la tassa di soggiorno, di 1,50€ a persona al giorno, i ragazzi under 12 non pagano. La tassa deve essere pagata all'arrivo, in contanti e contestualmente vi verranno richiesti i passaporti.

FamilyKitchenBarbecue

4.96 out of 5 average rating, 168 reviews
Guest favourite
Farm stay in Siena

Agriturismo La Villa - Il Castagno, Pool & Garden

Immersed in the green woods of the Senese hills, the beating heart of Tuscany, lies the La Villa estate. Characterized by a large park with swimming pool, gazebo, barbecue area and relaxation area, the farmhouse stands out for its strong link with the Tuscan tradition: a suggestive path will guide you to discover the woods surrounding the farm among olive trees and fields of lavender in bloom, among which you can forget the passage of time and enjoy the charms of nature.

FamilyKitchenLong stay

4.98 out of 5 average rating, 222 reviews
Top Guest favourite
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

Casa al Gianni - Capanna

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!

FamilyIndoor spacesCheckout

4.93 out of 5 average rating, 294 reviews
Top Guest favourite
An aerial view highlights a stone farmhouse nestled within lush greenery, surrounded by mature trees. The structure features a terracotta-tiled roof and a charming porch. A pathway leads to a smaller stone building, providing a sense of harmony with the natural landscape.
Villa in Sarteano

Casale in pietra in Val D’Orcia

Casale toscano del '800 con pietre a vista immerso nella meravigliosa campagna Toscana con uno splendido panorama sulla Val di Chiana. E' circondato da un parco di 6 ettari con un uliveto di 300 piante. Si trova a Sarteano, nel paese, un antico borgo medioevale con un castello da sogno, conosciuto per il Festival della Musica e del Jazz che si svolge alla fine dell'estate. Siamo nella bellissima Val d'Orcia, patrimonio naturale dell'umanità dall'UNESCO dal 2004.

FamilyIndoor spacesSleep quality

4.98 out of 5 average rating, 160 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.

Indoor spacesKitchenHospitality

4.98 out of 5 average rating, 107 reviews
Guest favourite
A stone patio is shown, featuring a small table set with two chairs. The entrance to the cottage is visible, accompanied by wooden shutters. Lush greenery surrounds the area, providing a serene environment.
Cottage in Ponte Feccia

Country cottage C&M immerso nel verde love Tuscany

Country cottage in pietra , indipendente nella campagna Toscana in provincia di Siena ,con ampio giardino, portico e gazebo. La nostra casa e' situata nella campagna del comune di Chiusdino, a soli 5 minuti dai due paesi principali Monticiano e Chiusdino e 10 minuti dalla splendida Abbazia di.Galgano . 30 minuti da Siena , da Monteriggioni , un'ora da Firenze e 30/40min minuti dal mare. Soli 20 minuti dalle belle Terme del Petriolo .

KitchenFamilyNearby

4.94 out of 5 average rating, 203 reviews

Popular amenities for Monticiano family-friendly rentals

Family-friendly home rentals with a hot tub

Family-friendly home rentals with a pool

Top Guest favourite
A scenic view of the Tuscan hills is framed by clusters of pink roses in the foreground. The rolling landscape features layers of green and gold fields, softly fading into the horizon under a clear sky.
Apartment in Montalcino

Panoramic Country Suite Montalcino

KitchenIndoor spacesAmenities

4.9 out of 5 average rating, 406 reviews
Top Guest favourite
An outdoor pool area is surrounded by olive trees and vineyards, with sun loungers and shaded umbrellas arranged on the deck. Soft sunlight bathes the scene, highlighting the peaceful setting. A gravel path leads around the pool, inviting relaxation amid the natural landscape.
Apartment in Monteriggioni

Comfort Apartment tra i vigneti del Chianti

FamilyKitchenHospitality

4.93 out of 5 average rating, 455 reviews
Top Guest favourite
A solitary tree stands prominently in the foreground, framed against a vast landscape. Below, the coastline stretches toward the horizon, with the sea shimmering in the distance. The view includes a charming town nestled among the lush greenery of the surrounding hills.
Villa in Castagneto Carducci

sea view villa with private infinity pool

FamilyIndoor spacesValue

4.99 out of 5 average rating, 124 reviews
Top Guest favourite
Home in Montaione

Cercis - La Palmierina

KitchenFamilyWalkability

4.96 out of 5 average rating, 147 reviews
Top Guest favourite
An aerial view captures the agriturismo surrounded by lush green fields and a neatly arranged row of tall cypress trees. The inviting pool reflects the serene landscape, and the winding dirt road leads towards the property, nestled amid the picturesque Crete Senesi.
Apartment in Asciano

Loggiato 1 in agriturismo con piscina condivisa

KitchenIndoor spacesSleep quality

4.97 out of 5 average rating, 188 reviews
Top Guest favourite
A rustic agriturismo is framed by vibrant greenery and blooming flowers. Outdoor seating is provided by several light-colored chairs and a patterned table. The stone building showcases large windows, which invite natural light into the space, while a welcoming atmosphere is suggested by the well-maintained garden.
Farm stay in Pienza

Castello di Spedaletto, Val d'Orcia, Pienza

Indoor spacesKitchenPets

4.97 out of 5 average rating, 185 reviews
Top Guest favourite
Cottage in Monticiano

Typical Tuscan Cottage with swimming pool and park

Indoor spacesFamilyLong stay

4.95 out of 5 average rating, 42 reviews
Superhost
Villa in Monticiano

Independent country house with private pool

FamilyIndoor spacesAccuracy

4.7 out of 5 average rating, 20 reviews