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

Total holiday rentals
Explore 20 holiday rentals in Montaione

Nightly prices starting at
Montaione holiday rentals start at $98 AUD per night before taxes and fees

Verified guest reviews
Over 170 verified reviews to help you choose

Pet-friendly accommodation
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

Wi-Fi availability
20 of Montaione holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Montaione rentals

4.8 Average rating
Montaione stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated family-friendly rentals in Montaione
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Villa Il Vecchio Pozzo in Tuscany
Immersed in nature where you can relax at the sight of a magnificent panorama. Gambassi Terme is located in the center of Tuscany a few kilometers from the main cities of art (Florence, Siena, Pisa). The historic center can also be reached on foot and in summer various village festivals and various shows are organized. The apartment consists of kitchen, living room, sofa, fireplace, bathroom, a double bedroom and a dressing room with two single beds. On the back there is a loggia with breathtaking views and the pool with sun loungers and umbrellas. The presence of the large garden and the proximity to the family garden equipped with pets (chickens, pigeons and ducks) make it an ideal place even for a family with children. Immersed in the countryside where you can relax in peace and quiet at the view of a magnificent view ,but also easily reachable on foot the center where there are supermarkets, bars, bars, etc.
FamilyKitchenValue
4.94 out of 5 average rating, 146 reviews
Infinity pool in Chianti 1
Our house is a part of a stone farmhouse completely independent from the rest of the adjacent property. Arranged on three floors, on the ground floor there is a large entrance hall, a large living room with fireplace, a bedroom with 1 double bed and a bathroom with window. On the first floor there are two bedrooms (2 +2 beds) with a bathroom with window. In the basement, at garden level, there is the kitchen and the dining room. From the kitchen you access the outside where you will find an area for outdoor dining with a large dining table under a pergola. You then go down towards the garden with barbecue area.
FamilyIndoor spacesDecor
5.0 out of 5 average rating, 143 reviews
Casa al Gianni - Hut
Hi, we’re Cristina and Carmelo! We look forward to welcoming you to ‘Casa al Gianni’, our farm stay 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 companionship of our animals. It’s an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a holiday; it’s a return to our roots. This haven of peace will stay with you in your heart. We look forward to welcoming you!
FamilyKitchenEV charging
4.93 out of 5 average rating, 292 reviews
Cosy Tuscan Home near Florence & San Gimignano
A WELCOMING NEST where tradition and modern comfort come together. Perfect for those who want to slow down, relax and experience the most authentic Tuscany, away from the hustle and bustle. Imagine waking up in the heart of a Tuscan village, looking out over the square and starting your day in the peace and quiet of the local way of life. The apartment, which has been fully renovated and tastefully furnished, is located in the historic centre of Gambassi Terme, an ideal base for exploring the wonders of Tuscany.
KitchenIndoor spacesWalkability
4.99 out of 5 average rating, 130 reviews
Villa Gourmet Food, Pizza, Chef, Pool and Nature
Villa Gourmet Typical farmhouse in the heart of Tuscany with 6 bedrooms that can comfortably accommodate up to 14 guests. - Exclusive saltwater infinity pool - Gourmet cuisine - Large garden with private parking - Two Free Charging Station (3,75 KW) - Veranda with table and Weber barbecue by the pool - Children's play area and table tennis - Football pitch - Home Restaurant service available - Cooking class and pizza workshop using a wood-fired oven - Shuttle Services
FamilyIndoor spacesLayout
4.98 out of 5 average rating, 127 reviews
Il Fienile, Luxury Apartment in the Tuscan Hills
‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.
KitchenIndoor spacesBarbecue
5.0 out of 5 average rating, 233 reviews
Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can organise a private shuttle and local experiences directly. The apartment is available for 2 adults with the option 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 unique sunsets.
KitchenIndoor spacesAccuracy
5.0 out of 5 average rating, 352 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.
Indoor spacesKitchenNearby
4.98 out of 5 average rating, 107 reviews
Tenuta Collerucci | Poet's House
Tenuta Collerucci is a charming farmhouse located in the heart of the Tuscan countryside, just 4 km from the Etruscan town of Montaione in the Valdelsa area. Set on a beautiful hill, the estate is surrounded by vineyards and olive groves, offering stunning panoramic views of the Tuscan landscape. The farmhouse features four rustic-style apartments and a delightful swimming pool, making it an ideal retreat for relaxation and enjoying the region’s natural beauty.
Indoor spacesFamilyCheck-in
4.79 out of 5 average rating, 102 reviews
Tower Penthouse in small castle near Florence
900 year old Tower-Penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, history, convenience. (AC throughout). Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.
KitchenIndoor spacesParking
4.96 out of 5 average rating, 139 reviews
Lovely house in a scenic and paiceful location
This beautiful house is nestled in a quiet and panoramic location, making it the perfect spot to get away from it all. With three bedrooms, three bathrooms, and room for up to six guests, this is the perfect place for a group of friends or a large family to call home while exploring Tuscany. Spend your days hiking the picturesque landscape, wandering through charming villages, or simply relaxing in the lovely gardens of the house.
KitchenFamilyNearby
4.93 out of 5 average rating, 123 reviews
Cercis - La Palmierina
The apartment is part of a completely fenced estate of 60 hectares of unspoiled nature: more than 1000 olive trees, countless cypresses and fragrant forests create an idyllic environment for those seeking tranquility and silence. The Palmierina estate is near Castelfalfi (a true jewel of medieval architecture) and close to Florence (50 Km), Siena (50 Km), and Pisa (50 Km). There are two golf courses nearby.
KitchenIndoor spacesBathroom
4.96 out of 5 average rating, 146 reviewsPopular amenities for Montaione family-friendly rentals
Family-friendly home rentals with a hot tub

A Big Dream in a Little Tower.
FamilyKitchenWi-Fi
4.95 out of 5 average rating, 221 reviews
Farmhouse in Chianti with Swimming Pool
FamilyIndoor spacesParking
4.99 out of 5 average rating, 516 reviews
Green Dome @ The Land Before Time Retreats
Indoor spacesFamilyAccuracy
4.95 out of 5 average rating, 185 reviews
Le Rose Apartment in Tuscany
Indoor spacesKitchenBackyard
4.83 out of 5 average rating, 112 reviews
Nada Home
Indoor spacesKitchenParking
4.87 out of 5 average rating, 217 reviews
SuiteLouise.pool, Hot Tub,homeGym & private Garden
FamilyIndoor spacesParks
4.91 out of 5 average rating, 128 reviews
Il Fienile, Cottage in the country with Jacuzzi
FamilyKitchenDecor
4.96 out of 5 average rating, 198 reviews
Tuscany Country House Villa Claudia
KitchenIndoor spacesTV
4.94 out of 5 average rating, 134 reviewsFamily- and pet-friendly home rentals

Borgo Ripostena – No. 9 Oil Mill
Indoor spacesKitchenOutdoor spaces
4.94 out of 5 average rating, 118 reviews
Belforti Tower
KitchenIndoor spacesLocation
4.99 out of 5 average rating, 138 reviews
Casa Giulia on Via Francigena
KitchenIndoor spacesValue
4.95 out of 5 average rating, 300 reviews
Poggio Massiccioli
KitchenIndoor spacesWalkability
4.92 out of 5 average rating, 389 reviews
Florence Sunset Hills • Giogoli
FamilyKitchenAccuracy
4.88 out of 5 average rating, 342 reviews
Authentic among stones and bricks
FamilyIndoor spacesView
4.82 out of 5 average rating, 145 reviews
Farmhouse in Chianti
Indoor spacesKitchenQuiet
4.95 out of 5 average rating, 221 reviews
Countryside Cottage With View - Le Papere apt
KitchenIndoor spacesCheckout
4.88 out of 5 average rating, 139 reviewsFamily-friendly home rentals with a pool

Countryside Dream farm in Tuscany
KitchenIndoor spacesBathroom
4.98 out of 5 average rating, 200 reviews
Tuscany cottage for 4 people with swimming pool
FamilyKitchenBathroom
4.87 out of 5 average rating, 85 reviews
Villa Strozzi - Vinuta di Collegalli
Indoor spacesKitchenCleanliness
5.0 out of 5 average rating, 44 reviews
Casa Camelia - Your authentic Tuscan getaway
Indoor spacesFamilyHospitality
4.94 out of 5 average rating, 16 reviews
Villa Via Francigena
FamilyIndoor spacesLocation
4.96 out of 5 average rating, 74 reviews
Villa Il Goro
KitchenFamilyAccuracy
4.79 out of 5 average rating, 19 reviews
Agriturismo Poggio Leone - Ulivo Apartment
FamilyIndoor spacesView
4.75 out of 5 average rating, 36 reviews
Tuscan Villa with Pool & Jacuzzi, San Gimignano
Indoor spacesFamilyHeating
4.98 out of 5 average rating, 90 reviewsDestinations to explore
- 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
- Val di Luce
- Pitti Palace





