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

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.

Montalcino Townhouse with Private Garden & Spa
A luxury apartment that blends traditional elements with all the modern comforts and some contemporary wall art. The apartment is centrally located in the upper part of town, only around the corner from the main square, in the limited traffic area. You can drive close by to download the luggage. The closest free car park is located at less than 10 minutes walk. Please note that to reach the house you need to walk a fairly steep street: it may not be ideal for those with mobility problems.

[9 minutes from Montalcino] Elegant House Mafalda
Comfortable apartment located in the heart of Orcia valley (val d’Orcia); strategic location for visiting the sought-after medieval villages of Montalcino, Castiglione d’Orcia, Pienza, Montepulciano and San Quirico d’Orcia. In addition, Torrenieri (Montalcino) has always been considered an excellent starting point for various trekking itineraries. The balcony in one of the suites overlooks the splendid surrounding Sienese hills!! Finally, there is free parking near the house.

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.

Flat, Agriturismo "Biofattoria l'Upupa"
The flat is on the first floor of a classic Tuscan farmhouse called ‘Biofattoria l'Upupa’. Magnificent hillside location between the Val d'Orcia and the Crete Senesi. Suitable for families with children. Consisting of kitchen, large living room, bathroom with shower, 1 double bedroom and 1 bedroom with bunk beds. There is a double sofa bed in the living room. The flat is equipped with wifi. Free parking on private property. Complete breakfast kit including homemade cakes.

Apartment in a detached villa - Val d'Orcia
In a detached villa, a cozy Tuscan-style apartment recently and tastefully renovated and located in a land rich in history. A few kilometers from the city of art and on the Via Francigena, the apartment can be a base for nature or food and wine tours. From a beautiful terrace overlooking the panorama you can enjoy your meals, admire the sunset and observe the majestic and magnificent medieval fortress From 03/22/18, municipal tourist tax: €1 per person from 12 years old

"Landscape Notes" Suite
The 80 sqm Suite "Note di paesaggio" is located on the second floor of a historic building where it meets the landscape of the Val d'Orcia. It is divided into several rooms including a furnished double bedroom with air conditioning overlooking the terrace, a living room with a panoramic view, a study with a desk, a marble bathroom with shower, and another double bedroom without air conditioning . You can enjoy a 30sqm terrace and its suggestive view of the countryside.

Alma Vignoni - Vignoni Val d'Orcia - Bagno Vignoni
Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

Mascagni Farmhouse in Val d'Orcia, Pienza
Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

House of the Jujube
Facing the old medieval walls of this ancient city, the location of the house will make you feel relaxed thanks to the peacefulness of the countryside and the vitality of the centre. Bathed in the gorgeous sunlight from sunrise to sunset, Casa delle Giuggiole will give you a sensation of lightness and freedom. Look through any one of the many windows and you can admire both the astonishing landscape of the Val d'Orcia and the typical Tuscan roofs.

Panoramic nest in Montalcino
A completely independent accommodation recently refurbished - from the design to the furnishings - directly by the host. It is composed of a living room with a fully equipped kitchen and a bedroom with bathroom. The peculiarity of the property is the extremely favorable location in the historic center, with a splendid terrace with panoramic garden on the Val d'Orcia, with barbecue, hammock, sink and outdoor shower.

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 Montalcino family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi

"Sunflower" apartment with view of Siena

San Giovanni in Poggio, villa Meriggio 95mq

Beautiful renovated barn in Tuscany

Villa di Geggiano – Guesthouse

Your Private Tuscan Retreat

Poggio dell'orso.Traditional Casale. Amazing views

Fontarcella, H&R- mediterranean home with jacuzzi
Family- and pet-friendly home rentals

Casa del Passerino

La Perla del Lago Holiday home

Resort Panoramic view - Free parking

Stuart White Tea Central Panoramic & Garden

Mafuccio Farmhouse - "Casa di Rigo"

Michelangelo: entire space in the heart of Tuscany

Amazing view of Val d'Orcia Pienza

Your Tuscan oak tree house, enchanting Val d'Orcia
Family-friendly home rentals with a pool

Family Forest - Pool in the Crete Senesi

Podere La Castellina - No. 1 COTTAGE

Spinosa Apartment in Podere Capraia

Countryside Dream farm in Tuscany

Mimosa Apartment - Poggio al Vento

Tuscan countryside, peace and relaxation 10 minutes from Siena

Wonderful Loft in Villa with Pool in Chianti

Stunning Tuscan apartment for 2
Quick stats about vacation rentals that are family-friendly in Montalcino

Total vacation rentals
Explore 530 vacation rentals in Montalcino

Nightly prices starting at
Montalcino vacation rentals start at $70 CAD per night before taxes and fees

Verified guest reviews
Over 13,760 verified reviews to help you choose

Pet-friendly vacation rentals
Find 310 rentals that welcome pets

Vacation rentals with a pool
290 properties feature pools

Rentals with dedicated workspaces
220 properties have a dedicated workspace

Wifi availability
500 of Montalcino vacation rentals include wifi access

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

4.8 Average rating
Montalcino stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Provence Vacation rentals
- Rome Vacation rentals
- Molfetta Vacation rentals
- Milan Vacation rentals
- Nice Vacation rentals
- Florence Vacation rentals
- Venice Vacation rentals
- Francavilla al Mare Vacation rentals
- Naples Vacation rentals
- Cannes Vacation rentals
- Italian Riviera Vacation rentals
- Bologna Vacation rentals
- Bed and breakfasts Montalcino
- Rentals with outdoor seating Montalcino
- Rentals with an EV charger Montalcino
- Rentals with a firepit Montalcino
- Cottage rentals Montalcino
- Rentals with pools Montalcino
- Rentals with breakfast Montalcino
- Smoking-friendly rentals Montalcino
- Rentals with a sauna Montalcino
- Vacation home rentals Montalcino
- Fitness-friendly rentals Montalcino
- Pet-friendly rentals Montalcino
- Villa rentals Montalcino
- Rentals with a fireplace Montalcino
- Farmstay rentals Montalcino
- Rentals with a hot tub Montalcino
- Luxury rentals Montalcino
- Rentals with a washer and dryer Montalcino
- Rentals with a patio Montalcino
- Condo rentals Montalcino
- Hotel rentals Montalcino
- House rentals Montalcino
- Apartment rentals Montalcino
- Family-friendly rentals Siena
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Lake Trasimeno
- Lake Bolsena
- Feniglia
- Cala Violina
- Gulf of Baratti
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Cala Di Forno
- Tenuta Le Velette
- Marina di Grosseto beach
- Castiglion del Bosco Winery
- Riva del Marchese
- Golf Club Toscana
- Santa Maria della Scala
- Cavallino Matto
- Pubblico Palace
- Cantina Stefanoni
- CavallinoMatto
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Podere La Marronaia, Sosta alle Colonne
- Casa Del Cioccolato Perugina
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Things to do Montalcino
- Food and drink Montalcino
- Nature and outdoors Montalcino
- Things to do Siena
- Sightseeing Siena
- Tours Siena
- Nature and outdoors Siena
- Art and culture Siena
- Food and drink Siena
- Things to do Tuscany
- Sports activities Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Wellness Tuscany
- Food and drink Tuscany
- Entertainment Tuscany
- Sightseeing Tuscany
- Tours Tuscany
- Things to do Italy
- Tours Italy
- Food and drink Italy
- Sports activities Italy
- Wellness Italy
- Nature and outdoors Italy
- Entertainment Italy
- Art and culture Italy
- Sightseeing Italy