
Family-friendly vacation rentals in Radicondoli
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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 spacesLaundry
4.93 out of 5 average rating, 197 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!
KitchenFamilyAccuracy
4.93 out of 5 average rating, 294 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!
KitchenFamilyPool
4.92 out of 5 average rating, 628 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 spacesValue
5.0 out of 5 average rating, 352 reviews
Podere La Castellina - No. 4 FICO
Apartment in stone and brick inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of the Montagnola Senese. The apartment located on the first floor can comfortably accommodate 4 people (2+2 children) and includes: - large living room with TV, sofa and 2 single beds - kitchen with oven - master bedroom - bathroom with shower Panoramic pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue are available to guests.
KitchenIndoor spacesAir conditioning
4.96 out of 5 average rating, 110 reviews
Villa di Geggiano - Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.
Indoor spacesKitchenBreakfast
4.99 out of 5 average rating, 155 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 spacesKitchenView
4.98 out of 5 average rating, 127 reviews
Agriturismo La Villa - L'Olivo, Pool & Hot Tub
Immersed in the green woods of the Senese hills, the beating heart of Tuscany, lies the La Villa estate. Characterized by a large park with swimming pool, gazebo, barbecue area and relaxation area, the farmhouse stands out for its strong link with the Tuscan tradition: a suggestive path will guide you to discover the woods surrounding the farm among olive trees and fields of lavender in bloom, among which you can forget the passage of time and enjoy the charms of nature.
FamilyIndoor spacesWifi
4.98 out of 5 average rating, 241 reviews
Country cottage C&M surrounded by greenery, love Tuscany
Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.
KitchenFamilyAccess
4.94 out of 5 average rating, 204 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 spacesGetting around
4.98 out of 5 average rating, 108 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.
FamilyIndoor spacesNearby
4.96 out of 5 average rating, 139 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.
FamilyIndoor spacesBreakfast
4.95 out of 5 average rating, 190 reviewsPopular amenities for Radicondoli family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury frescoed apartment in the historical center
KitchenIndoor spacesComfort
4.97 out of 5 average rating, 117 reviews
Farmhouse in Chianti with Swimming Pool
FamilyIndoor spacesBiking
4.99 out of 5 average rating, 516 reviews
Domus Nannini - Loggia Salimbeni SPA
KitchenIndoor spacesLocation
4.96 out of 5 average rating, 156 reviews
A Big Dream in a Little Tower.
Indoor spacesKitchenShared spaces
4.95 out of 5 average rating, 222 reviews
La Pieve - the house next to the church
Indoor spacesKitchenParking
4.97 out of 5 average rating, 117 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
Indoor spacesFamilyHeating
4.91 out of 5 average rating, 101 reviews
Beautiful Country House, near Siena with jacuzzi
Indoor spacesKitchenComfort
4.96 out of 5 average rating, 104 reviews
White lily with a view of Siena
FamilyKitchenSleep quality
4.92 out of 5 average rating, 115 reviewsFamily- and pet-friendly home rentals

Typical Tuscan Country House WITH A/C
FamilyKitchenParks
4.98 out of 5 average rating, 294 reviews
Torre dei Belforti
Indoor spacesFamilySleep quality
4.99 out of 5 average rating, 138 reviews
Apartment in a Tuscan farmhouse at Le Pietre Vive
Indoor spacesKitchenAccuracy
4.92 out of 5 average rating, 359 reviews
Beautiful medieval village!!!
FamilyKitchenWalkability
4.99 out of 5 average rating, 475 reviews
Eleutherìa: Cozy Cottage in the heart of Tuscany
Indoor spacesKitchenNearby
4.96 out of 5 average rating, 124 reviews
Casa Sabina
Indoor spacesFamilyNearby
4.98 out of 5 average rating, 129 reviews
Florence Sunset Hills • Giogoli
Indoor spacesFamilyHospitality
4.88 out of 5 average rating, 343 reviews
Suite in Castello di Valle
FamilyIndoor spacesCheckout
4.88 out of 5 average rating, 129 reviewsFamily-friendly home rentals with a pool

Cercis - La Palmierina
KitchenIndoor spacesComfort
4.96 out of 5 average rating, 147 reviews
Charming farmhouse with garden, views & pool
Indoor spacesKitchenCheck-in
4.92 out of 5 average rating, 233 reviews
sea view villa with private infinity pool
KitchenIndoor spacesView
4.99 out of 5 average rating, 124 reviews
Infinity pool in Chianti 1
Indoor spacesFamilyBathroom
5.0 out of 5 average rating, 143 reviews
Il Castello di Ferrano - Castle in Tuscany
Indoor spacesKitchenLocation
4.99 out of 5 average rating, 227 reviews
Apartment in Old Farmhouse
FamilyKitchenBiking
4.96 out of 5 average rating, 51 reviews
Il melograno, Podere il Giglio
FamilyIndoor spacesBreakfast
5.0 out of 5 average rating, 34 reviews
Monolocale Antico Fienile
Indoor spacesKitchenQuiet
5.0 out of 5 average rating, 15 reviewsDestinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Cala Violina
- Parco Regionale Della Maremma
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Uffizi Gallery
- Gulf of Baratti
- Piazza della Repubblica
- Spiaggia Di Sansone
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Parco delle Cascine
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





