
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.

Casa al Gianni - Fig
Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!

Farmhouse Fattoria La Parita
Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

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.

Villa with View for Family & Friends, in Tuscany
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!

Apartment in Tuscan farm house.
Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.

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

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.

Country cottage C&M surrounded by greenery, love Tuscany
Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.

"Villa Daisy" overlooking Siena
Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Farmhouse on a winery
Detached house, within the Cantina Lapone winery, panoramic position, renovated. It is 6 km from Orvieto, Lapone area, fully paved road, on 3 floors, consisting of two bedrooms, 2 bathrooms, living room with fireplace and kitchen area, terrace. Non-exclusive pool use. Min 2 days. Address: Strada del Lapone no. 8, Orvieto (TR).

BEAUTIFUL FARM HOUSE with SWIMMING POOL in TUSCANY
Our little farm is a beautiful location for a relaxing vacation with a private swimming pool( open around . the 10th of May).We are close to the naturally occurring hot springs of Petriolo and 30 km. far from Siena. We are only two km. from Pari, an ancient medieval village.
Popular amenities for Monticiano family-friendly rentals
Family-friendly home rentals with a hot tub

A Big Dream in a Little Tower.

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Villa unesco heritage, Jacuzzi & garden. BB Daria

Villa'Colombaiolo di Marciano', 28

La Pieve - the house next to the church

Tuscany View - Villa Arianna

EcoLodge – modern design in a peaceful panoramic location
Family- and pet-friendly home rentals

The Eagle and the Olive Tree

Beautiful medieval village!!!

Historic Estate near Siena with swimmingpool

Holiday in antique farm, Belvedere

In Tuscany Rooms

Casa Luigi Suite with exclusive pool

Panoramic penthouse in the ancient village

Poggio Bicchieri Holiday Farm - Memoria apartment
Family-friendly home rentals with a pool

Infinity pool in Chianti area

Siena - apartment in the countryside near Siena

Podere La Castellina - No. 1 COTTAGE

Tuja

Charming farmhouse with garden, views & pool

Independent country house with private pool

Podere Casalino - Il Gatto

La Villa Farmhouse - Chestnut, Pool & Garden
Quick stats about holiday rentals that are family-friendly in Monticiano

Total holiday rentals
Explore 40 holiday rentals in Monticiano

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

Verified guest reviews
Over 840 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
30 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 outdoor seating Monticiano
- Villa rentals Monticiano
- Rentals with pools Monticiano
- Rentals with a fireplace Monticiano
- Rentals with a washing machine and dryer Monticiano
- Rentals with a patio Monticiano
- Smoking-friendly rentals Monticiano
- House rentals Monticiano
- Flat rentals Monticiano
- Pet-friendly rentals Monticiano
- Family-friendly rentals Siena
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Stazione Santa Maria Novella
- Lake Trasimeno
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Cala Violina
- Mercato Centrale
- Fortezza da Basso
- Piazza della Repubblica
- Uffizi Gallery
- Del Chianti
- Piazzale Michelangelo
- Pitti Palace
- Palazzo Vecchio
- Spiagge Bianche
- Boboli's Garden
- Parco delle Cascine
- Spiaggia Di Barbarossa
- Gulf of Baratti
- Spiaggia di Capo Bianco
- Basilica of Santa Croce
- Medici Chapel





