
House vacation rentals in Radda in Chianti
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Top-rated house rentals in Radda in Chianti
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Charming converted Hayloft overlooking the Chianti Hills
Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available
FamilyLocationQuiet
4.97 out of 5 average rating, 305 reviews
Casa al Gianni - The Simignano Barn
Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!
ValueLocationAmenities
4.97 out of 5 average rating, 194 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.
ValueFamilyWifi
4.99 out of 5 average rating, 113 reviews
"La Casa di Maria Luce"® with panoramic terrace
"La Casa di Maria Luce"® Selvolini is located in the medieval village of Lecchi in Chianti (8 km from Gaiole) in the heart of the Chianti Classico region, with ample space to comfortably accommodate 4-5 people. It consists of a kitchen-living room, 2 beautiful bedrooms, and 2 full bathrooms. 50 meters from the grocery store for first necessities, tobaccos, a bar-room for breakfasts and quick lunches, a great restaurant a short walk from the house. The large furnished terrace offers a beautiful view of the countryside.
FamilyLocationBiking
4.96 out of 5 average rating, 244 reviews
Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.
LocationFamilyTV
4.99 out of 5 average rating, 136 reviews
Charming estate with views. A/C in the bedrooms
The estate finely restored in 2016 is accessorized with all the confort you need for an holiday dedicated to the relax or to excursions The Breathtaking view on the Chianti Classico's vineyards give to the estate a unique feature perfect for a romantic holiday, small group of friend or a little family. The estate is provided of external Jacuzzi, private garden and we can arrange for you bike or hike excursions. The Village of Gaiole in Chianti is just 5 minutes away by car.
LocationFamilyWalkability
4.86 out of 5 average rating, 294 reviews
The Chianti Classico Sunset
If you are looking for an idyllic location in the heart of Chianti Classico, surrounded by the vineyards and olive groves of the beautiful Tuscan hills, on the estate of a historic 16th-century villa, then come to our barn!! It has a dominant position with a breathtaking view, where you can enjoy stunning sunsets. The total independence of the house, the cozy garden, and the large loggia allow you to spend your stay in total peace of mind. Our reviews are your best guarantee.
LocationFamilyIndoor spaces
4.98 out of 5 average rating, 242 reviews
Casa Giulia di Sopra Farmhouse
The CASA GIULIA DI SOPRA apartment, renovated in 2022 and located on the first floor, is a portion of an ancient farmhouse located in the heart of Chianti Classico. It is surrounded by the vineyards of Villa Calcinaia, an estate owned by the Capponi Counts since 1524. The apartment is 130 meters away from the shared swimming pool, open from May to October. The apartment has an outdoor area with a table and chairs where guests can dine and enjoy a glass of wine at sunset.
LocationFamilyAmenities
4.95 out of 5 average rating, 103 reviews
La Loggia
Immerse yourself in the authentic Tuscan dream. "La Loggia" is a charming home in the heart of Chianti Classico, just 300 meters on foot from the historic center of Radda. It offers the perfect blend of countryside quietness and village convenience, featuring a large private garden with breathtaking panoramic views over vineyards and a beautiful glass-enclosed loggia. The perfect oasis to relax and enjoy the sunset after exploring Siena, Florence, and nearby wineries.
LocationValueKitchen
4.93 out of 5 average rating, 152 reviews
The Chianti window
A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.
LocationFamilyPets
4.9 out of 5 average rating, 133 reviews
Nada Home
3 comfortable, fully air-conditioned double bedrooms, each with its own private bathroom, in the heart of Chianti, ideally located between Florence, Siena and San Gimignano. A welcoming, well-kept home in the peaceful Tuscan countryside. Fully equipped kitchen with dishwasher, oven and bar area, plus a laundry room with washing machine and dryer. Private garden for your exclusive use with a private hydromassage pool, heated in winter upon request 🌷
FamilyLocationCheck-in
4.87 out of 5 average rating, 215 reviews
Casa Al Poggio in Chianti Shire
Casa al Poggio is a 145 sqm Tuscan country house in the heart of Chianti. The ground floor features a large living area with a kitchen and fireplace. Upstairs are 2 double bedrooms and an open room with a versatile sofa bed (set up as a double or 2 singles). A relaxing bathroom offers a shower, bathtub, and Chianti views. Outside, a terrace in the gravel garden awaits for your evenings. Perfect for experiencing authentic Tuscany!
ValueFamilyIndoor spaces
4.96 out of 5 average rating, 330 reviewsPopular amenities for Radda in Chianti house rentals
House rentals with a pool

Leonardo - Chianti/Siena, Florence, San Gimignano.
LocationFamilyAccuracy
4.97 out of 5 average rating, 118 reviews
Villa Lolù with private heated swimming-pool
LocationFamilyHot tub
4.97 out of 5 average rating, 159 reviews
Infinity pool in Chianti 1
ValueLocationGrill
5.0 out of 5 average rating, 141 reviews
Palazzo Monaci - Pool in the Crete Senesi
ValueFamilySleep quality
4.96 out of 5 average rating, 138 reviews
Ancient Barn in Chianti with Pool
FamilyLocationBiking
4.89 out of 5 average rating, 125 reviews
Cercis - La Palmierina
FamilyLocationParking
4.96 out of 5 average rating, 144 reviews
SuiteLouise.pool, Hot Tub,homeGym & private Garden
LocationFamilyWalkability
4.91 out of 5 average rating, 124 reviews
Casa Luigi Suite with exclusive pool
FamilyLocationAccess
4.95 out of 5 average rating, 121 reviewsWeekly house rentals

Terrazza a Campana
FamilyLocationNearby
4.89 out of 5 average rating, 120 reviews
Domus Nannini - Loggia Salimbeni SPA
FamilyLocationIndoor spaces
4.96 out of 5 average rating, 156 reviews
Love in Chianti
ValueFamilyTV
4.96 out of 5 average rating, 242 reviews
BEAUTIFUL OLD BARN IN CHIANTI
FamilyLocationBathroom
4.99 out of 5 average rating, 141 reviews
Casa Nataly Chianti - Jeky Stay
ValueFamilyGetting around
4.86 out of 5 average rating, 155 reviews
Torretta Apartment
ValueFamilyGetting around
4.97 out of 5 average rating, 128 reviews
Villa le Scope 5*
LocationFamilyWalkability
4.98 out of 5 average rating, 49 reviews
Townhouse in Chianti
FamilyLocationSleep quality
4.84 out of 5 average rating, 38 reviewsPrivate house rentals

Casa San Ripa: Relax Oasis with Private Pool
FamilyLocationPool
4.98 out of 5 average rating, 49 reviews
Chianti Amore Mio
FamilyLocationCheck-in
4.95 out of 5 average rating, 22 reviews
Wonderful country house
LocationFamilyLayout
4.94 out of 5 average rating, 97 reviews
Apartment with stunning view on the vineyards
FamilyLocationNearby
4.97 out of 5 average rating, 31 reviews
La Casa del Briga
ValueFamilyBreakfast
4.98 out of 5 average rating, 52 reviews
Medieval fortress restored with pool by Vacavilla
LocationFamilyComfort
5.0 out of 5 average rating, 13 reviews
Villa Eroica
LocationFamilyPool
4.97 out of 5 average rating, 31 reviews
Poggiolo
ValueLocationComfort
5.0 out of 5 average rating, 32 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Mugello Circuit
- Mercato Centrale
- Spiagge Bianche
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Porta Elisa
- Stadio Artemio Franchi





