
Family-friendly holiday rentals in Montalcino
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Montalcino

Total holiday rentals
Explore 40 holiday rentals in Montalcino

Nightly prices starting at
Montalcino holiday rentals start at $114 AUD per night before taxes and fees

Verified guest reviews
Over 1,520 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Montalcino holiday rentals include Wi-Fi access

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

4.9 Average rating
Montalcino stays are highly rated by guests—averaging 4.9 out of 5!
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.

Charming Tuscan Villa with View forFamily&Friends
Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visits & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Villa di Geggiano – Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Rural Tuscany | Family farmstay with restaurant
Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.
La Piazzetta - Cozy open space in the historic center of Montepulciano
Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Then go outside and admire the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, and stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana Valley.

"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.

Podere Pereti Nuovi – Modern Tuscan Villa
Podere I Pereti was entirely build by our grandfather Remo in the 1970's. My siblings and I spent most of our summers on the porch with our grandparents watching sunsets and admiring the view of the Val d'Orcia. Entirely surrounded by vineyards and olive groves. Nonno Remo, besides having a building company, proudly produced Orcia red wine that was consumed by the family. From the 150 olive trees, every November we filled our tanks with green gold olive oil.

La Casetta di Brunello, very panoramic with terrace
WE'RE WORKING FOR YOU. ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

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.

Castel Brunello - 2 doublebed rooms + terrace
Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.

Elegant farmhouse Siena
The apartment of 200 square meters is part of a farmhouse of the 1600, it easily accommodates 6 people, it has 3 large bedrooms, a large living room, a kitchen with fireplace, two bathrooms and a breathtaking view, overlooking the Tuscan countryside up to Montalcino .
Popular amenities for Montalcino family-friendly rentals
Family-friendly home rentals with a hot tub

Casa al Gianni - The Simignano Barn

Villa unesco heritage, Jacuzzi & garden. BB Daria

Wine Experience Villa in Montepulciano

Casa Dolce Toscana | Panoramic Suite with View

Villa in Montepulciano with a Pool

EcoLodge – modern design in a peaceful panoramic location

Studio (2+1) in Val d'Orcia - Tuscany

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
Family- and pet-friendly home rentals

Poggio Bicchieri Holiday Farm - Memoria apartment

In Tuscany Rooms

Appaloosa - Apartment for couples and families

Tuscan cottage with an heavenly view

Pink like the sunset sky

Under the sunset, Montepulciano

Tuscany on the terrace, downtown Montepulciano

Terra Delle Sidhe, Seggiano, Tuscany, Italy
Family-friendly home rentals with a pool

A paradise in Montepulciano...

Private Chianti Cottage, Garden & Vineyard Views

TUSCANY farm house SWIMMING POOL

Comfort Apartment in the Chianti Vineyards

CasaROSA Brunello vineyards

Suite, private apt for 2/4, pool

Country House in the Crete Senesi

Podere La Castellina - No. 1 COTTAGE
Destinations to explore
- Rentals with an EV charger Montalcino
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- Farmstay rentals Montalcino
- Condo rentals Montalcino
- Rentals with a sauna Montalcino
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- Smoking-friendly rentals Montalcino
- Holiday home rentals Montalcino
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- Rentals with breakfast Montalcino
- Rentals with a fire pit Montalcino
- Family-friendly rentals Siena
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Lake Trasimeno
- Lake Bolsena
- Cala Violina
- Feniglia
- Parco Regionale Della Maremma
- Gulf of Baratti
- Del Chianti
- Cascate del Mulino
- Centro Storico Orvieto
- Avignonesi Winery Fattoria Le Capezzine
- Mount Amiata
- La Scarzuola
- CavallinoMatto
- Antinori nel Chianti Classico
- Siena Cathedral
- Palazzo Pubblico
- Vulci
- Ugolino Golf Club
- Val di Chiana
- Valdichiana Outlet Village
- Terme San Filippo
- Abbey of Monte Oliveto Maggiore
- Abbey of Sant'Antimo
- Casa Barthel
- Things to do Montalcino
- Food and drink Montalcino
- Things to do Siena
- Food and drink Siena
- Sightseeing Siena
- Tours Siena
- Sports activities Siena
- Art and culture Siena
- Entertainment Siena
- Nature and outdoors Siena
- Things to do Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Sports activities Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Things to do Italy
- Tours Italy
- Entertainment Italy
- Food and drink Italy
- Art and culture Italy
- Wellness Italy
- Nature and outdoors Italy
- Sports activities Italy
- Sightseeing Italy







