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

Casa al Gianni - Oak
Hi, we’re Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism property in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds, and the warmth 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 in your soul. We look forward to welcoming you!
4.93 out of 5 average rating, 244 reviews
Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient family-run property from the 1600s located in the beautiful hills of Chianti in Tuscany, with the possibility of arranging a private shuttle and local experiences directly with our family. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with incomparable sunsets.
5.0 out of 5 average rating, 352 reviews
Monteriggioni Castello, holiday house in Tuscany
Our accommodation is a historic building that dates back to the construction of the castle. It has been recently restored and furnished with attention to every detail. It is very welcoming and has all the most modern amenities. Tourists who decide to be our guests will have the advantage of living in the medieval environment of the castle, taking advantage of all the conveniences. They will feel pampered and have the opportunity to return home having lived a unique and unforgettable experience.
4.95 out of 5 average rating, 297 reviews
Podere Casalino - Il Gatto
Set in the peaceful countryside near the Monteriggioni Castle, Il Casalino is the result of our love for restoring an old Tuscan farmhouse. My husband and I have carefully created two apartments for our guests: Il Gatto and La Pergola. We want you to feel at home from the very first moment. If you have any questions, feel free to message me: I will reply as quickly as possible. We truly look forward to welcoming you to Il Casalino and sharing this special place with you! Warm regards, Laura
4.91 out of 5 average rating, 117 reviews
DorminColle - Tuscan-style apartment
Appartamento luminoso e spazioso, composto da confortevole camera matrimoniale con tv, condizionatore portatile, con al suo interno bagno completo di doccia e servizi igienici. Terzo posto letto situato in caratteristica area soppalcata con travi in legno dotato di letto. Ampia cucina dotata di lavastoviglie, macchina del caffè, microonde, erogatore acqua filtrata, Salone con tv e divano, sala da pranzo con vista sul Borgo Antico. Parcheggio gratuito a 150 mt visibile dell’appartamento.
4.97 out of 5 average rating, 253 reviews
Villa dei 2 Ulivi (Abbadia Isola)
FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)
4.97 out of 5 average rating, 174 reviews
The House in the Alley – Colle di Val d'Elsa
Very central location, house completely renovated in 2023, cozy and quiet, equipped with every comfort. Independent entrance. Located 50 meters from Piazza Arnolfo di Cambio and 300 meters from the historic center (reachable on foot or by elevator), for those traveling by bus the stop is only 100 meters away. Strategic location for visiting Siena, Florence, San Gimignano, Volterra, Chianti Hills and for those who want to travel the Via Francigena or visit the Elsa River Park.
4.99 out of 5 average rating, 135 reviews
Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
4.98 out of 5 average rating, 107 reviews
Agriturismo La Villa - Il Ciliegio, Pool & Garden
We are pleased to welcome you to our Cherry Tree House, the last newly renovated jewel of the Agriturismo La Villa. Located on second floor, built among the rocks of the typical Senese countryside, our new home will be ready to lull you into all kinds of comforts: free wifi, swimming pool, barbecue area, air conditioning, smart TV. private parking, wood and garden, just 40 steps away, overlooking our lavender and olive grove.
4.95 out of 5 average rating, 146 reviews
Comfort Apartment in the Chianti Vineyards
Apartment on the upper floor of the structure characterized by a wonderful view of the Chianti hills, olive groves or the patio. Renovated while maintaining the charm of their ancient walls but adding every comfort. It includes a living room, kitchenette, a double bedroom, a private bathroom with shower, and air conditioning.
4.93 out of 5 average rating, 455 reviews
Next to castle of Villa-Siena. heart Francigena
The house has a special charm that I'm sure will captivate you. You will be excited to sip a glass of wine in the beautiful Hague or stroll through the ancient paths of the Via Francigena (stage n. 32 from Monteriggioni to Siena) which overlooks the living room .
4.84 out of 5 average rating, 158 reviews
Siena Countryside Colle Ciupi
Countryside Villa apartment. Located in the nearby of Siena (Colle Ciupi, 10 kms away) Ground floor: Kitchen, living room with fireplace, bathroom with shower. First Floor: 3 Double Bedrooms and 2 bathrooms, outdoor with courtyard and huge garden
4.9 out of 5 average rating, 217 reviewsPopular amenities for Monteriggioni family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury frescoed apartment in the historical center
4.97 out of 5 average rating, 116 reviews
Villa di Geggiano - Guesthouse
4.99 out of 5 average rating, 155 reviews
Domus Nannini - Loggia Salimbeni SPA
4.96 out of 5 average rating, 156 reviews
La Pieve - the house next to the church
4.97 out of 5 average rating, 117 reviews
Farmhouse in Chianti with Swimming Pool
4.99 out of 5 average rating, 516 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
4.91 out of 5 average rating, 100 reviews
A Big Dream in a Little Tower.
4.95 out of 5 average rating, 221 reviews
White lily with a view of Siena
4.92 out of 5 average rating, 113 reviewsFamily- and pet-friendly home rentals

Above the Post Office
4.98 out of 5 average rating, 126 reviews
Secret Garden Siena
4.98 out of 5 average rating, 220 reviews
Poggio Massiccioli
4.92 out of 5 average rating, 389 reviews
Farmhouse in Chianti, Siena Tuscany
4.83 out of 5 average rating, 168 reviews
Manor House - IlVillinoFarmhouse
4.93 out of 5 average rating, 255 reviews
Typical Tuscan Country House WITH A/C
4.98 out of 5 average rating, 294 reviews
Villa Capanna, Private Pool, Breathtaking Views
4.89 out of 5 average rating, 309 reviews
Beautiful medieval village!!!
4.99 out of 5 average rating, 473 reviewsFamily-friendly home rentals with a pool

Private Chianti Cottage, Garden & Vineyard Views
4.99 out of 5 average rating, 137 reviews
Explore Chianti from a Charming Stone House
4.98 out of 5 average rating, 123 reviews
Infinity pool in Chianti 1
5.0 out of 5 average rating, 142 reviews
Villa Isabella
4.96 out of 5 average rating, 209 reviews
Dolce vita in Chianti. Pool and Relaxation
4.85 out of 5 average rating, 354 reviews
Cercis - La Palmierina
4.96 out of 5 average rating, 146 reviews
Stone House with Exclusive Pool Codilungo in Chianti
4.98 out of 5 average rating, 218 reviews
Apartment Melogranowith great views
4.88 out of 5 average rating, 183 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Stazione Santa Maria Novella
- Cala Violina
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Gulf of Baratti
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace





