
Family-friendly vacation rentals in Radicondoli
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Radicondoli
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

La Casetta
“La Casetta”, is a new restored enchanting apartment immersed in the splendid Tuscan countryside, only 2 kms from the medieval village of Casole d'Elsa in Siena province. Situated in a old farm complex with private entrance, large private garden, and access to the communal swimming pool. Furnished with utmost care down to the finest detail. Ideal for a relaxing, regenerative week with family or friends, emerged in an uncontaminated natural landscape. Possibility of excursions on foot and by bicycle in an evocative natural setting of lush forests and gentle hills of rare beauty. One can enjoy local dishes of the wonderful Tuscan tradition in many of the nearby restaurants or organize splendid home-cooked meals with the barbecue in the garden. Ideally situated for visits the many nearby towns and cities rich in art and beauty: 30 mins to Siena, 1 hour to Florence ,30 mins to San Gimignano and Volterra, 45 mins to the Chianti area. La Casetta is the ideal place to regenerate your body and mind. (We are the same owners of “La Senesina" apartment near Siena check out our rating on the web! Our 5 stars ratings are your warranty for a great stunning vacation)
KitchenIndoor spacesComfort
4.93 out of 5 average rating, 194 reviews
Ancient 17th-century farmhouse in Chianti, Tuscany
Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing exclusive services and experiences tailored to you. 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 swimming pool with a relaxation area on a panoramic terrace, with wonderful views of the castle, hills, and vineyards and breathtaking sunsets.
KitchenIndoor spacesAmenities
5.0 out of 5 average rating, 218 reviews
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!
Indoor spacesFamilyHiking
4.93 out of 5 average rating, 244 reviews
Relaxation and charm in the Chianti hills
Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.
FamilyIndoor spacesCheck-in
4.99 out of 5 average rating, 113 reviews
Poggio Bicchieri Holiday Farm - Memoria apartment
Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!
KitchenFamilyBathroom
4.92 out of 5 average rating, 620 reviews
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.
FamilyIndoor spacesCheck-in
4.92 out of 5 average rating, 357 reviews
Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.
KitchenFamilyOutdoor spaces
4.97 out of 5 average rating, 160 reviews
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360Ëš view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.
Indoor spacesFamilyHospitality
4.99 out of 5 average rating, 113 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.
KitchenFamilyValue
4.99 out of 5 average rating, 137 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.
KitchenIndoor spacesAccuracy
4.98 out of 5 average rating, 105 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.
FamilyIndoor spacesLong stay
4.95 out of 5 average rating, 145 reviews
Green Dome @ The Land Before Time Retreats
Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.
Indoor spacesFamilySleep quality
4.95 out of 5 average rating, 169 reviewsPopular amenities for Radicondoli family-friendly rentals
Family-friendly home rentals with a hot tub

Villa di Geggiano - Guesthouse
KitchenIndoor spacesAccuracy
4.99 out of 5 average rating, 155 reviews
La Pieve - the house next to the church
FamilyKitchenCondition
4.97 out of 5 average rating, 115 reviews
Luxury frescoed apartment in the historical center
FamilyKitchenGetting around
4.98 out of 5 average rating, 113 reviews
A Big Dream in a Little Tower.
FamilyKitchenBiking
4.95 out of 5 average rating, 219 reviews
Typical Tuscan country house
Indoor spacesKitchenShared spaces
4.99 out of 5 average rating, 431 reviews
Palazzo Monaci - Pool in the Crete Senesi
Indoor spacesFamilyOutdoor spaces
4.96 out of 5 average rating, 138 reviews
Domus Nannini - Loggia Salimbeni SPA
FamilyIndoor spacesComfort
4.96 out of 5 average rating, 156 reviews
Nada Home
FamilyIndoor spacesPool
4.87 out of 5 average rating, 215 reviewsFamily- and pet-friendly home rentals

Typical Tuscan Country House WITH A/C
Indoor spacesKitchenAccess
4.98 out of 5 average rating, 290 reviews
Florence Sunset Hills • Giogoli
FamilyKitchenBackyard
4.88 out of 5 average rating, 338 reviews
Panoramic farmhouse with pool - Big Apartment
KitchenIndoor spacesHiking
4.98 out of 5 average rating, 99 reviews
Country cottage C&M surrounded by greenery, love Tuscany
KitchenIndoor spacesCleanliness
4.95 out of 5 average rating, 200 reviews
Villa Capanna, Private Pool, Breathtaking Views
Indoor spacesFamilyAir conditioning
4.89 out of 5 average rating, 307 reviews
Beautiful medieval village!!!
KitchenFamilyBreakfast
4.99 out of 5 average rating, 470 reviews
TOWER apartment in small castle near Florence
KitchenFamilyCondition
4.92 out of 5 average rating, 569 reviews
Poggio Massiccioli
FamilyKitchenWifi
4.92 out of 5 average rating, 386 reviewsFamily-friendly home rentals with a pool

Castel Brunello - 2 doublebed rooms + terrace
FamilyIndoor spacesSleep quality
4.99 out of 5 average rating, 117 reviews
Loggiato 3 apartment in Tuscany near Siena
KitchenIndoor spacesQuiet
4.93 out of 5 average rating, 201 reviews
Stone House with Exclusive Pool Codilungo in Chianti
KitchenIndoor spacesGrill
4.98 out of 5 average rating, 216 reviews
Charming farmhouse with garden, views & pool
FamilyKitchenGrill
4.92 out of 5 average rating, 232 reviews
Il Castello di Ferrano - Castle in Tuscany
FamilyIndoor spacesParking
4.99 out of 5 average rating, 226 reviews
Il melograno, Podere il Giglio
KitchenFamilyOutdoor spaces
5.0 out of 5 average rating, 32 reviews
Apartment in Old Farmhouse
KitchenFamilySleep quality
4.96 out of 5 average rating, 50 reviews
House 7 mins walk to center w/ private pool
FamilyIndoor spacesWifi
4.76 out of 5 average rating, 29 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)
- Cala Violina
- Stazione Santa Maria Novella
- Parco Regionale Della Maremma
- Spiagge Bianche
- Mercato Centrale
- Pisa Centrale Railway Station
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Spiaggia Di Sansone
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





