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Family-friendly vacation rentals in Montaione

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Montaione

  • Total vacation rentals

    Explore 20 vacation rentals in Montaione

  • Nightly prices starting at

    Montaione vacation rentals start at ﺩ.ﺇ 257 per night before taxes and fees

  • Verified guest reviews

    Over 170 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Montaione vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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.

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Guest favorite
The crystal-clear pool reflects the charming stone villa and surrounding olive trees. A wooden table and chairs are visible on a patio, inviting relaxation. Planters with vibrant flowers add color to the landscape, enhancing the serene ambiance of the countryside.
Villa in Gambassi Terme
4.94 out of 5 average rating, 146 reviews

Villa Il Vecchio Pozzo in Toscana

Immersa nella natura dove è possibile rilassarsi alla vista di un magnifico panorama. Gambassi Terme è situato al centro della Toscana a pochi km dalle principali città d'arte (Firenze, Siena, Pisa). Il centro storico è raggiungibile anche a piedi e nei periodi estivi vengono organizzate varie feste paesane e spettacoli vari. L'appartamento è composto da cucina, soggiorno, divano, camino, bagno, una camera matrimoniale e una camerina con due letti singoli. Sul retro c'è un loggiato con vista mozzafiato e la piscina con lettini e ombrelloni. La presenza dell'ampio giardino e la vicinanza all'orto di famiglia munito di animali domestici (galline, piccioni e papere) ne fanno un luogo ideale anche per una famiglia con bambini. Immerso nella campagna dove è possibile rilassarsi in pace e tranquillita' alla vista di un magnifico scorcio ,ma facilmente raggiungibile anche a piedi il centro dove ci sono supermarket,bar. ecc

FamilyKitchenAir conditioning

Top guest favorite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.93 out of 5 average rating, 292 reviews

Casa al Gianni - Hut

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!

Indoor spacesFamilyNearby

Top guest favorite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5.0 out of 5 average rating, 352 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.

KitchenIndoor spacesGrill

Top guest favorite
Condo in Gambassi Terme
4.99 out of 5 average rating, 130 reviews

Cosy Tuscan Home near Florence & San Gimignano

A COZY NEST where tradition and modern comfort meet. 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 the day in harmony with the local tranquility and rhythms. The apartment, completely renovated and tastefully furnished, is located in the historic center of Gambassi Terme, a strategic location for exploring the wonders of Tuscany.

Indoor spacesFamilyLocation

Top guest favorite
A sunlit pool area features a spacious salt-water pool with a surrounding deck. Several lounge chairs are arranged with umbrellas, providing shaded seating. A rustic stone building serves as a backdrop, displaying traditional Italian architectural elements and large windows that invite natural light.
Villa in Orentano
4.98 out of 5 average rating, 127 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 spacesNearby

Top guest favorite
Villa in Montecatini Val di Cecina
4.99 out of 5 average rating, 138 reviews

Torre dei Belforti

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

FamilyKitchenSleep quality

Top guest favorite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5.0 out of 5 average rating, 233 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.

Indoor spacesKitchenGetting around

Top guest favorite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 107 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.

KitchenFamilyLong stay

Superhost
Apartment in Montaione
4.79 out of 5 average rating, 101 reviews

Tenuta Collerucci | Casa Poeta

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.

FamilyIndoor spacesWifi

Top guest favorite
The historic tower-penthouse villa is surrounded by lush greenery and trees. The three-story structure is characterized by its earthy facade and wooden shutters. Well-maintained gardens with various plants create a serene outdoor environment, enhancing the villa's tranquil charm and historical significance.
Castle in Bagno A Ripoli
4.96 out of 5 average rating, 139 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.

KitchenFamilyWalkability

Guest favorite
A rustic villa features large glass panels that offer views of the surrounding greenery. The spacious outdoor patio area is equipped with a dining set and lounge chairs. Towering trees and well-maintained grass frame the property under a bright blue sky, enhancing the serene countryside setting.
Home in San Miniato
4.93 out of 5 average rating, 123 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.

Indoor spacesKitchenBackyard

Top guest favorite
An aerial view reveals the rustic stone farmhouse surrounded by lush greenery and vineyards. The inviting pool is set within a well-maintained garden, complemented by outdoor seating and barbecue areas, offering a peaceful retreat in the heart of the Tuscan countryside.
Apartment in Gavignano
4.92 out of 5 average rating, 389 reviews

Poggio Massiccioli

Cozy apartment for 4 people furnished in Tuscan style and with exposed beams immersed in the rolling hills of the Tuscan countryside. Guests have access to a furnished garden, free Wi-Fi, a shared swimming pool, a wood-burning oven, a barbecue, and a washing machine. The apartment was converted from a charming 19th-century stone farmhouse, recently renovated in the Tuscan tradition and divided into three comfortable apartments.

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Popular amenities for Montaione family-friendly rentals