
Family-friendly holiday 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 - 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.

Tuscan cottage with an heavenly view
Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

La Casa di Bruna
LA CASA DI BRUNA Un appartamento finemente ristrutturato, arredato con amore e cura nei dettagli, si trova all’interno di un palazzo storico L’ingresso si apre su un salone con comodissimo divano collegato ad un'ampia e confortevole cucina Dalla sala accediamo alla terrazza con affaccio sulla fortezza dove si possono godere tramonti meravigliosi Sullo stesso piano troviamo un bagno e una luminosa camera matrimoniale Al piano superiore vi è il secondo bagno ed un'altra confortevole camera

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.

Appartamento in villino indipendente-Val d’Orcia
In villetta indipendente accogliente appartamento in stile toscano recentemente e finemente ristrutturato e situato in una terra ricca di storia. A pochi km da città d'arte e sulla via Francigena, l'appartamento può essere base per percorsi naturalistici o enogastronomici. Da una bella terrazza sul panorama potrete godere i vostri pasti, ammirare il tramonto ed osservare la maestosa e magnifica Rocca medioevale .Dal 22/03/18 tassa di di soggiorno comunale:1 € a persona a partire dai 12 anni

Verde - I prati in Toscana
Appartamento composto da 1 camera matrimoniale , cucina attrezzata, ampio soggiorno e bagno Tv, BBq, ( mettiamo a disposizione la lavatrice dalle 9 alle 20 che è nella nostra lavanderia a chi ne fa richiesta ) . Consigliamo l'auto in quanto abitiamo in campagna, sia per essere indipendenti , sia per visitare la magnifica toscana Ti piacerá l'ambiente esterno perché é magico di giorno e di notte Parcheggio e wifi gratis Posizione strategica per visitare la Toscana e l'Umbria.

[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
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.

Suite "Note di Paesaggio"
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.

Casa delle Giuggiole
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.
Popular amenities for Montalcino family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi

Appartamento "Sunflower" con vista su Siena

San Giovanni in Poggio, villa Meriggio 95mq

Splendido fienile ristrutturato in Toscana

Your Private Tuscan Retreat

Villa di Geggiano - Guesthouse

Poggio dell'orso.Traditional Casale. Amazing views

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

Back Home - Apartment in Pienza

Mascagni Farmhouse in Val d'Orcia Pienza

Podere Casa Cecilia

Esplora la natura al centro di Vigneti Chianti

Stuart White Tea Central Panoramic & Garden

Monteriggioni Castello, holiday house in Tuscany

Luxurious Medieval Tower & Private Concierge
La Piazzetta -Accogliente open space nel centro storico di Montepulciano
Family-friendly home rentals with a pool

Podere Guidi

Appartamento Spinosa a Podere Capraia

Podere Ampella Casa Bella Vista

Appartamento Mimosa - Poggio al Vento

Sperone: two floors apartment with pool

Campagna Toscana, pace e relax a 10 min da Siena

Stunning Tuscan apartment for 2

Agriturismo La Villa - Il Castagno, Pool & Garden
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $216 SGD | $217 SGD | $239 SGD | $261 SGD | $264 SGD | $283 SGD | $304 SGD | $319 SGD | $291 SGD | $251 SGD | $226 SGD | $227 SGD |
| 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 Montalcino

Total holiday rentals
Explore 530 holiday rentals in Montalcino

Nightly prices starting at
Montalcino holiday rentals start at $65 SGD per night before taxes and fees

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

Pet-friendly holiday rentals
Find 310 rentals that welcome pets

Holiday rentals with a pool
290 properties feature pools

Rentals with dedicated workspaces
220 properties have a dedicated workspace

Wifi availability
500 of Montalcino holiday 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
- Rentals with outdoor seating Montalcino
- Flat rentals Montalcino
- Rentals with a fireplace Montalcino
- Pet-friendly rentals Montalcino
- Villa rentals Montalcino
- Smoking-friendly rentals Montalcino
- Rentals with an EV charger Montalcino
- Luxury rentals Montalcino
- Bed and breakfasts Montalcino
- House rentals Montalcino
- Rentals with a hot tub Montalcino
- Cottage rentals Montalcino
- Rentals with pools Montalcino
- Rentals with a patio Montalcino
- Holiday home rentals Montalcino
- Hotel rooms Montalcino
- Rentals with a washing machine and dryer Montalcino
- Apartment rentals Montalcino
- Rentals with a sauna Montalcino
- Farm stay rentals Montalcino
- Rentals with breakfast Montalcino
- Rentals with a firepit Montalcino
- Fitness-friendly 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
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Tenuta Le Velette
- Cala Di Forno
- Castiglion del Bosco Winery
- Golf Club Toscana
- Marina di Grosseto beach
- Riva del Marchese
- Santa Maria della Scala
- Pubblico Palace
- Cavallino Matto
- CavallinoMatto
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Podere La Marronaia, Sosta alle Colonne
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Madonna del Latte
- Podere Il Cocco
- Things to do Montalcino
- Food and drink Montalcino
- Things to do Siena
- Sightseeing Siena
- Art and culture Siena
- Food and drink Siena
- Nature and outdoors Siena
- Sports activities Siena
- Tours Siena
- Things to do Tuscany
- Sports activities Tuscany
- Art and culture Tuscany
- Wellness Tuscany
- Nature and outdoors Tuscany
- Tours Tuscany
- Sightseeing Tuscany
- Food and drink Tuscany
- Entertainment Tuscany
- Things to do Italy
- Food and drink Italy
- Nature and outdoors Italy
- Art and culture Italy
- Sports activities Italy
- Sightseeing Italy
- Tours Italy
- Entertainment Italy
- Wellness Italy




