
Family-friendly holiday rentals in Monticiano
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Monticiano
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Pieve di Caminino Historic Farm
Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Casa Marino
Our cozy home is located closed to Siena, the Val d'Arbia and the Val d'Orcia, Unesco World Heritage site; you can easily reach the most beautiful town around Siena and Florence, like San Gimignano, Volterra, Montalcino. Rooms are wide and comfortable. The apartament is bright and you can enjoy a nice view on the Tuscan countryside from its windows. It is located in the old hamlet of Casciano. Suitable for couples and families with kids. Parking area about 50 metres from the apartment.

Farmhouse with pool in Chianti
Agriturismo Il Colle is located on one of the Chianti hills. The structure 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 The apartment is on the first floor of the main farmhouse, with independent access and garden with trees. The rustic furnishings in the classic Tuscan style, with wooden beam ceilings and terracotta floors give a characteristic touch to the environment.

Monteriggioni Castello, holiday house in Tuscany
Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Terra Delle Sidhe, Seggiano, Tuscany, Italy
Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

Green – The meadows in Tuscany
Apartment consisting of 1 double bedroom, equipped kitchen, large living room and bathroom TV, BBQ, (we provide the washing machine from 9 to 20 which is in our laundry room to those who request it). We recommend a car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and Wi-Fi Strategic location for visiting Tuscany and Umbria.

Agriturismo La Villa - Il Ciliegio, Pool & Garden.
We are pleased to welcome you to our Cherry Tree House, the last newly renovated jewel of the Agriturismo La Villa. Located on second floor, built among the rocks of the typical Senese countryside, our new home will be ready to lull you into all kinds of comforts: free wifi, swimming pool, barbecue area, air conditioning, smart TV. private parking, wood and private garden, just 40 steps away, overlooking our lavender and olive grove.

TOWER apartment in small castle near Florence
Romantic, Historically unique, Magical atmosphere, 360 degree views of the countryside and Florence. Great retreat for digital nomads, or simply to retreat from the hustle and bustle. Convenient for Chianti and Tuscany explorations. A/C in 2 rooms. Cooking class and wine tasting available. If you'd like to add more space and comfort, book the TOWER PENTHOUSE: double the space, a large kitchen, another bathroom. Perfect for families!

Tuscan countryside, peace and relaxation 10 minutes from Siena
Our accommodation is close to Siena, therefore to nightlife, the city center but also to the small airport of Ampugnano, parks, and public transport. You'll love our place for its light, the comfort of the bed, the kitchen, the intimacy, and the high ceilings. Our apartment is suitable for couples, solo adventurers, business travelers, families (with children) and furry friends (pets).

Casa al Gianni - Capanna
Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!
Popular amenities for Monticiano family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi

Amazing Tuscany Villa, FREE parking

San Giovanni in Poggio, villa Meriggio 95mq

Beautiful renovated barn in Tuscany

Your Private Tuscan Retreat

Nada Home

Fontarcella, H&R- mediterranean home with jacuzzi

La Pieve - the house next to the church
Family- and pet-friendly home rentals

Belforti Tower

Authentic Tuscan Country House WITH A/C

Explore nature in the center of Vigneti Chianti

Podere Guidi

Le Splandole Farm – Crete Senesi

Poggio dell'orso.Traditional Casale. Amazing views

Mafuccio Farmhouse - "Casa di Rigo"

Secret Garden Siena
Family-friendly home rentals with a pool

Panoramic Country Suite Montalcino

Infinity pool in Chianti area

Il Camino: cosy & artfully inspired country house

Podere La Castellina - No. 1 COTTAGE

Holiday in antique farm, Belvedere

Agriturismo I Gelsi

Manuela apartment with pool in farmhouse

Wonderful Loft in Villa with Pool in Chianti
When is the best time to visit Monticiano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 105 | € 106 | € 89 | € 130 | € 123 | € 126 | € 129 | € 123 | € 107 | € 135 | € 122 | € 133 |
| Avg. temp | 8°C | 8°C | 11°C | 13°C | 18°C | 22°C | 25°C | 25°C | 21°C | 17°C | 12°C | 9°C |
Quick stats about holiday rentals that are family-friendly in Monticiano

Total holiday rentals
Explore 50 holiday rentals in Monticiano

Nightly prices starting at
Monticiano holiday rentals start at € 43 per night before taxes and fees

Verified guest reviews
Over 830 verified reviews to help you choose

Pet-friendly holiday rentals
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

Wifi availability
40 of Monticiano holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Monticiano rentals

4.8 Average rating
Monticiano stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Rentals with pools Monticiano
- Rentals with outdoor seating Monticiano
- House rentals Monticiano
- Rentals with a patio Monticiano
- Smoking-friendly rentals Monticiano
- Rentals with a washing machine and dryer Monticiano
- Flat rentals Monticiano
- Pet-friendly rentals Monticiano
- Rentals with a fireplace Monticiano
- Villa rentals Monticiano
- Family-friendly rentals Siena
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Santa Maria Novella
- Mercato Centrale
- Piazzale Michelangelo
- Lake Trasimeno
- Duomo di Firenze
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Spiagge bianche
- Cala Violina
- Uffizi Gallery
- Fortezza da Basso
- Gulf of Baratti
- Piazza della Repubblica
- Pitti Palace
- Spiaggia di Capo Bianco
- Parco delle Cascine
- The Boboli Gardens
- Kite Beach Fiumara
- Spiaggia Di Barbarossa
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Spiaggia della Padulella
- Medici Chapels
- Palazzo Vecchio




