
Family-friendly holiday 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)
Indoor spacesKitchenBeach
4.93 out of 5 average rating, 194 reviews
Casa al Gianni - Oak
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!
KitchenIndoor spacesSleep quality
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.
Indoor spacesKitchenCleanliness
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!
KitchenFamilyDecor
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.
Indoor spacesKitchenBreakfast
4.92 out of 5 average rating, 357 reviews
Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange 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 spacesHospitality
5.0 out of 5 average rating, 350 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
Indoor spacesKitchenCleanliness
4.98 out of 5 average rating, 126 reviews
Podere La Castellina - No. 3 JUNIPER
Stone and brick apartment inside the "Podere la Castellina" in the magnificent natural park of Montagnola Senese. The apartment located on the first floor can comfortably accommodate 5 people (4+1) and includes: - large living room with fireplace and sofa bed - kitchen - 2 bedrooms : one with a double bed and one with two single beds - two baths Panoramic pool, solarium and terrace with breathtaking views, equipped with wood-burning oven and barbecue.. shared
FamilyKitchenAmenities
4.9 out of 5 average rating, 142 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.
KitchenFamilyBarbecue
4.98 out of 5 average rating, 105 reviews
Farmhouse in Chianti with Swimming Pool
Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is located on the ground floor of the main farmhouse, with independent access and private space. The care taken in the restoration and furnishing make the house particularly welcoming, respecting the rural style.
KitchenIndoor spacesBathroom
4.99 out of 5 average rating, 510 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 spacesCleanliness
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 spacesFamilyHospitality
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
Indoor spacesKitchenAccuracy
4.99 out of 5 average rating, 155 reviews
Luxury frescoed apartment in the historical center
KitchenIndoor spacesBathroom
4.98 out of 5 average rating, 113 reviews
La Pieve - the house next to the church
FamilyIndoor spacesCleanliness
4.97 out of 5 average rating, 115 reviews
Domus Nannini - Loggia Salimbeni SPA
Indoor spacesKitchenComfort
4.96 out of 5 average rating, 156 reviews
Wp Relais Borgo Vignalunga
Indoor spacesFamilyAmenities
4.94 out of 5 average rating, 145 reviews
Palazzo Monaci - Pool in the Crete Senesi
KitchenIndoor spacesSolo travel
4.96 out of 5 average rating, 138 reviews
Nada Home
Indoor spacesFamilyOutdoor spaces
4.87 out of 5 average rating, 215 reviews
"Red Rose" apartment with view of Siena.
FamilyIndoor spacesAmenities
4.94 out of 5 average rating, 287 reviewsFamily- and pet-friendly home rentals

Florence Sunset Hills • Giogoli
FamilyKitchenWi-Fi
4.88 out of 5 average rating, 338 reviews
Country cottage C&M surrounded by greenery, love Tuscany
FamilyIndoor spacesOutdoor spaces
4.95 out of 5 average rating, 200 reviews
Typical Tuscan Country House WITH A/C
Indoor spacesFamilyHeating
4.98 out of 5 average rating, 290 reviews
Belforti Tower
FamilyIndoor spacesValue
4.99 out of 5 average rating, 137 reviews
Panoramic farmhouse with pool - Big Apartment
FamilyIndoor spacesNearby
4.98 out of 5 average rating, 99 reviews
Pink like the sunset sky
KitchenIndoor spacesBathroom
4.99 out of 5 average rating, 233 reviews
Beautiful medieval village!!!
Indoor spacesKitchenCheck-in
4.99 out of 5 average rating, 470 reviews
Poggio Massiccioli
FamilyIndoor spacesHeating
4.92 out of 5 average rating, 386 reviewsFamily-friendly home rentals with a pool

Loggiato 3 apartment in Tuscany near Siena
FamilyKitchenAccess
4.93 out of 5 average rating, 201 reviews
Castel Brunello - 2 doublebed rooms + terrace
KitchenFamilyLaundry
4.99 out of 5 average rating, 117 reviews
Charming farmhouse with garden, views & pool
FamilyIndoor spacesValue
4.92 out of 5 average rating, 232 reviews
The Castle of Ferrano - Castle in Tuscany
FamilyKitchenAir conditioning
4.99 out of 5 average rating, 226 reviews
Stone House with Exclusive Pool Codilungo in Chianti
Indoor spacesKitchenAccuracy
4.98 out of 5 average rating, 216 reviews
Leo's Romantic House
KitchenIndoor spacesHeating
5.0 out of 5 average rating, 65 reviews
The pomegranate, Podere il Giglio
Indoor spacesKitchenBathroom
5.0 out of 5 average rating, 32 reviews
Antico Fienile Studio Apartment
KitchenFamilyPets
5.0 out of 5 average rating, 14 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
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Piazza della Repubblica
- Spiaggia Di Sansone
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Spiaggia di Capo Bianco





