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

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.

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.

Bruna's House
LA CASA DI BRUNA A finely renovated apartment, furnished with love and attention to detail, is located inside a historic building The entrance opens onto a living room with a very comfortable sofa connected to a large and comfortable kitchen From the living room, we access the terrace overlooking the fortress where you can enjoy wonderful sunsets On the same floor, there is a bathroom and a bright double bedroom Upstairs is the second bathroom and another comfortable bedroom

Studio (2+1) in Val d'Orcia - Tuscany
A few steps from the historic center of medieval San Quirico d'Orcia and just 100 meters from the supermarket, a stay made of silence and the quiet passage of time, of days with a relaxing and regenerating atmosphere characteristic of the lifestyle in Val d'Orcia. The Taste of Tranquility is guaranteed by a 5000 sqm park that offers lawns and shady trees suitable for reading or simple relaxation. Ideal for a stay with an "antique" flavor", combined with all modern comforts.

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.

"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.

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.

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?

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

Amazing Tuscany Villa, FREE parking

Torretta Apartment

"Sunflower" apartment with view of Siena

Beautiful renovated barn in Tuscany

Casa al Gianni - The Simignano Barn

Poggio dell'orso.Traditional Casale. Amazing views
Wp Relais Villa Vignalunga

Tuscany View - Villa Arianna
Family- and pet-friendly home rentals

Casa Borgianni in Villa Caprera

Cantagalli Farmhouse, Mugellese Apartment.

Antico Borgo Ripostena – n. 9 Oil Mill

Archi, Rustic apartment in Tuscany

Luxury farmhouse Tuscany air condit swimming pool

Suite, private apt for 2/4, pool

Poggio Bicchieri Holiday Farm - Memoria apartment

La Villa Farmhouse - Chestnut, Pool & Garden
Family-friendly home rentals with a pool

Country chic house in a village,private pool,wiFi

Capanna, typical house in Chianti with pool

Terra Antica Suites & Villas - Montepulciano

Agriturismo I Gelsi

Beautiful medieval tower in Chianti

Il Fienile del Borgo – Monteriggioni

"La Loggia" Private Villa with Great Views

Charming cottage in Tuscany
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$34,518 GYD | G$34,728 GYD | G$38,284 GYD | G$41,840 GYD | G$42,259 GYD | G$45,397 GYD | G$48,744 GYD | G$51,045 GYD | G$46,652 GYD | G$43,933 GYD | G$43,514 GYD | G$45,815 GYD |
| 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 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 G$8,368 GYD per night before taxes and fees

Verified guest reviews
Over 14,240 verified reviews to help you choose

Pet-friendly vacation rentals
Find 310 rentals that welcome pets

Vacation rentals with a pool
280 properties feature pools

Rentals with dedicated workspaces
220 properties have a dedicated workspace

Wi-Fi availability
490 of Montalcino vacation rentals include wi-fi 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!
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- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Lake Bolsena
- Del Chianti
- Cala Violina
- Feniglia
- Cascate del Mulino
- Gulf of Baratti
- Avignonesi Winery Fattoria Le Capezzine
- CavallinoMatto
- Santa Maria della Scala
- Palazzo Pubblico
- Siena Cathedral
- Riserva Naturale Diaccia Botrona
- Ugolino Golf Club
- Antinori nel Chianti Classico
- Casa Barthel
- Castello di Verrazzano
- Abbey of Monte Oliveto Maggiore
- Parco Regionale Della Maremma
- Pozzo di San Patrizio
- Val di Chiana
- Girifalco Fortress
- Vulci
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