
Family-friendly holiday 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)
Indoor spacesFamilyLocation
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 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!
FamilyIndoor spacesAir conditioning
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!
Indoor spacesFamilyTV
4.92 out of 5 average rating, 626 reviews
Podere La Castellina - No. 4 FICO
Stone and brick apartment 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.
Indoor spacesKitchenAccuracy
4.96 out of 5 average rating, 110 reviews
Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.
Indoor spacesFamilyView
4.95 out of 5 average rating, 146 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.
Indoor spacesFamilyAir conditioning
5.0 out of 5 average rating, 352 reviews
La Villa farm stay - 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.
KitchenIndoor spacesValue
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.
KitchenFamilyAmenities
4.94 out of 5 average rating, 203 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 spacesComfort
4.98 out of 5 average rating, 107 reviews
[SAN LORENZO-DUOMO] Prestigious Historic Residence
Make your stay a unique experience and give yourself an emotion that will last for life. Located in the heart of Florence, this magnificent historic residence is the ideal solution for those looking for an exclusive and prestigious location to combine with a central position, perfect for easily visiting the main sites of interest, reachable in less than 10 minutes on foot. The apartment enjoys exclusive views of the Medici Chapels, offering a unique view.
KitchenIndoor spacesBreakfast
5.0 out of 5 average rating, 158 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 spacesLocation
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 spacesView
4.95 out of 5 average rating, 185 reviewsPopular amenities for Radicondoli family-friendly rentals
Family-friendly home rentals with a hot tub

Villa di Geggiano – Guesthouse
Indoor spacesKitchenCleanliness
4.99 out of 5 average rating, 155 reviews
Palazzo Monaci - Pool in the Crete Senesi
KitchenFamilyLaundry
4.96 out of 5 average rating, 142 reviews
Typical Tuscan country house
KitchenFamilyLaundry
4.99 out of 5 average rating, 432 reviews
Domus Nannini - Loggia Salimbeni SPA
FamilyKitchenAmenities
4.96 out of 5 average rating, 156 reviews
Luxury frescoed apartment in the historical center
KitchenFamilyWalkability
4.97 out of 5 average rating, 116 reviews
La Pieve - the house next to the church
FamilyIndoor spacesView
4.97 out of 5 average rating, 117 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
FamilyKitchenNearby
4.91 out of 5 average rating, 100 reviews
Beautiful Country House, near Siena with jacuzzi
Indoor spacesFamilyHospitality
4.96 out of 5 average rating, 104 reviewsFamily- and pet-friendly home rentals

Typical Tuscan Country House WITH A/C
Indoor spacesFamilyNearby
4.98 out of 5 average rating, 294 reviews
Belforti Tower
Indoor spacesFamilyDecor
4.99 out of 5 average rating, 138 reviews
Apartment in a Tuscan farmhouse at Le Pietre Vive
KitchenIndoor spacesSolo travel
4.92 out of 5 average rating, 359 reviews
Eleutherìa: Cozy Cottage in the heart of Tuscany
FamilyIndoor spacesDecor
4.96 out of 5 average rating, 123 reviews
Casa Sabina
KitchenIndoor spacesAccuracy
4.98 out of 5 average rating, 129 reviews
Beautiful medieval village!!!
KitchenFamilyHospitality
4.99 out of 5 average rating, 474 reviews
Florence Sunset Hills • Giogoli
FamilyIndoor spacesLocation
4.88 out of 5 average rating, 342 reviews
Suite in Castello di Valle
KitchenIndoor spacesAccess
4.88 out of 5 average rating, 128 reviewsFamily-friendly home rentals with a pool

Cercis - La Palmierina
Indoor spacesFamilyQuiet
4.96 out of 5 average rating, 147 reviews
The Castle of Ferrano - Castle in Tuscany
Indoor spacesFamilyHiking
4.99 out of 5 average rating, 227 reviews
sea view villa with private infinity pool
Indoor spacesKitchenCondition
4.99 out of 5 average rating, 124 reviews
Charming farmhouse with garden, views & pool
KitchenIndoor spacesWalkability
4.92 out of 5 average rating, 233 reviews
Infinity pool in Chianti 1
KitchenFamilyNearby
5.0 out of 5 average rating, 143 reviews
Apartment in Old Farmhouse
FamilyKitchenLocation
4.96 out of 5 average rating, 51 reviews
The pomegranate, Podere il Giglio
Indoor spacesFamilyDecor
5.0 out of 5 average rating, 33 reviews
Antico Fienile Studio Apartment
KitchenFamilyAir conditioning
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
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Stazione Santa Maria Novella
- Cala Violina
- Parco Regionale Della Maremma
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Gulf of Baratti
- Uffizi Gallery
- Piazza della Repubblica
- Spiaggia Di Sansone
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





