
House holiday rentals in Rocca San Casciano
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Top-rated house rentals in Rocca San Casciano
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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.
FamilyValueCondition
4.99 out of 5 average rating, 115 reviews
Love in Chianti
Welcome to the delightful cottage of Riccardo and Pauline, a small corner of love where colors and details are designed to give peace and quiet. You will find yourself immersed in the green Tuscan hills, in a breathtaking landscape where the renowned Chianti Classico wine is born. The area is ideal for walking and cycling. You will be close to the cities of art, such as Florence, Siena and Arezzo. Upon request and according to availability, we offer a paid shuttle service. We look forward to seeing you ❤️
LocationFamilyCondition
4.96 out of 5 average rating, 246 reviews
Infinity view
Completely renovated location with breathtaking views of the Valdarno. The ground floor consists of a living room with two windows overlooking the patio, fireplace, sofa bed, bathroom with large shower and modern kitchen with steel island, with three French windows to access the outdoor dining area with BBQ. The second floor consists of two double bedrooms each with its own bathroom with shower. The garden is well-kept, there are various relaxation corners, a sundeck and an infinity pool with hydrolysis
ValueFamilyBeach
4.88 out of 5 average rating, 204 reviews
Tuscan Villa 15 min from Florence, Parking, Garden
Relax in the rustic comfort of a Tuscan farmhouse and experience authentic Italian living in the Florentine countryside, just a 15 minute drive from the city. Set in a quiet residential countryside area on the hills of Fiesole, the property offers a peaceful stay surrounded by olive trees, a garden and unforgettable sunsets. The farmhouse dates back to the 14th century and was part of a traditional Tuscan estate. Having a car is essential to reach the house and to move around during your stay
LocationFamilyKitchen
4.97 out of 5 average rating, 143 reviews
TREEhouse / casaBARTHEL
casaBARTHEL is a perfect place for a vacation and an artist residency, immersed in the Tuscan landscape only 15' from the florentine Duomo. Come and live with us; enjoy the olive trees, the kitchen garden, our horse Astro and our family life style, away from the working rhythm. By providing wifi only in the communal courtyard we suggest to take a break from been connected with elsewhere and enjoy the 'here and now' . But if you need to work you can rent a portable private connection from us.
FamilyLocationCondition
4.88 out of 5 average rating, 821 reviews
The Chianti Classico Sunset
If you are looking for an idyllic location in the heart of the Chianti Classico region, 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 an amazing view, where you can enjoy breathtaking sunsets. The complete independence of the house, the welcoming garden and the large loggia allow you to enjoy your stay in total tranquillity. Our reviews are your best guarantee.
ValueLocationHiking
4.98 out of 5 average rating, 244 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.
FamilyLocationBathroom
4.95 out of 5 average rating, 106 reviews
Ancient Tuscan Rural Residence
An elegant independent peaceful panoramic rustic residence nestled amidts the scenic and gently rolling hills in Tuscany . This beautiful property is the ideal destination for those who want to experience and enjoy true Italian country living, recommended for families. PRIVATE SWIMMING POOL (which is located a few tens of meters from the villa in its own land ) and JACUZZI (located in the garden of the villa ) are open for our guests from June until the end of October.
FamilyLocationHiking
4.85 out of 5 average rating, 124 reviews
Casa Macchia /Florence charming villa private Pool
Casa Macchia (over 200m²): Historic Tuscan country house in a natural setting with magical views and tranquillity. Ideal for families and groups: 9 beds plus 3 children's beds and 1 toddler bed offer plenty of space and places to retreat. Highlights: Large pool, very well-equipped kitchen & outdoor kitchen (table for 10). Remodelled by the designer Willy Fleckhaus and used by a family. 12 hectares of private land guarantee absolute privacy.
FamilyLocationCondition
4.96 out of 5 average rating, 102 reviews
"La limonaia" - Romantic Suite
Romantic Suite immersed in the enchanting hills of Fiesole. It is the ideal place fot those looking for unique and exclusive experience of its kind characterized by suggestive views and unforgettable sunsets. The accommodation is part of an old 19th century Tuscan farmhouse surrounded by its own olive groves and woods. This is an ideal place for a relaxing holiday and privileged base for visiting the major centers of interest in Tuscany.
ValueLocationOutdoor spaces
4.99 out of 5 average rating, 320 reviewsGorgeous Villa with Postcard Views in Historical Florence
Share a bottle of Chianti on a flagstone terrace with a view of cypresses on rolling hills. This classic private villa is steeped in Old World charm—and inside it's a showpiece of contemporary design with an ultramodern kitchen and marble-tiled bathrooms. Enjoy the best of both worlds in Florence, close enough to walk to everything, far enough away to have solitude.
LocationValueCheck-in
4.98 out of 5 average rating, 168 reviews
Tuscany .Countryhouse on the Florence's hills
Recently renovated house in a 19th-century Tuscan farmhouse surrounded by hills, vineyards and olive groves, located in the Chianti area, 1 km from the village (Antella) and 20 minutes by car from the centre of Florence. The accommodation has air conditioning for the summer months, although the very thick stone walls ensure a pleasant temperature even in summer.
LocationFamilyBathroom
4.99 out of 5 average rating, 185 reviewsPopular amenities for Rocca San Casciano house rentals
House rentals with a pool

La Nepitella Old Barn House, Florence
ValueFamilyView
4.84 out of 5 average rating, 289 reviews
Country House w/ heated Pool near the City Centre
LocationFamilyPool
4.82 out of 5 average rating, 163 reviews
Podere Solatio - Tuscany Hills next to Florence
ValueFamilyWalkability
4.97 out of 5 average rating, 146 reviews
Romantic cosy flat - Toscana Italy
ValueFamilyComfort
4.99 out of 5 average rating, 102 reviews
Old Barn very close to Florence
ValueLocationAccess
4.96 out of 5 average rating, 157 reviews
Casetta Melograno – Cozy farmhouse in Chianti
FamilyLocationCondition
4.95 out of 5 average rating, 182 reviews
Villa Zanzi - Rooms, B&B
ValueFamilyBeach
4.93 out of 5 average rating, 200 reviews
Villa Podere Cerretino
LocationFamilyHospitality
5.0 out of 5 average rating, 67 reviewsWeekly house rentals

Country house with view (NO Jacuzzi)
LocationFamilySleep quality
4.87 out of 5 average rating, 124 reviews
Casa del Gelsomosino
ValueLocationOutdoor spaces
4.87 out of 5 average rating, 110 reviews
Sode del Mardello Farm
LocationOutdoor spacesIndoor spaces
4.92 out of 5 average rating, 12 reviews
Nature Retreat | Peace & Relax in the Hills
FamilyLocationAccess
4.95 out of 5 average rating, 66 reviews
beautiful villa in Chianti, panoramic garden
LocationFamilyKitchen
4.96 out of 5 average rating, 47 reviews
Villa Carla – Florence View, Tennis & Hot Tub
ValueLocationNearby
5.0 out of 5 average rating, 15 reviews
Casa del Moro
LocationValueQuiet
4.97 out of 5 average rating, 35 reviews
Authentic Stone Retreat: Hike & MTB
FamilyLocationIndoor spaces
4.75 out of 5 average rating, 4 reviewsPrivate house rentals

Villa "Othello's House"
FamilyValueOutdoor spaces
4.92 out of 5 average rating, 37 reviews
Historic residence 30 minutes from Florence
FamilyLocationHospitality
5.0 out of 5 average rating, 90 reviews
luxury villa in centre of tuscany
FamilyValueNearby
4.77 out of 5 average rating, 100 reviews
Tuscan vineyard house, near Florence
FamilyLocationAmenities
5.0 out of 5 average rating, 27 reviews
Independent cottage in the countryside
LocationValueGetting around
4.82 out of 5 average rating, 62 reviews
La Limonaia della Torretta | Florence Private Pool
LocationFamilyNearby
5.0 out of 5 average rating, 34 reviews
detached house ground floor
LocationValueNearby
5.0 out of 5 average rating, 14 reviews
Villa in Mugello, a stone's throw from the Autodromo
FamilyLocationOutdoor spaces
4.92 out of 5 average rating, 12 reviewsDestinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Bologna Center Town
- Ponte Vecchio
- Pinarella Di Cervia
- Mirabilandia
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Bologna Fiere
- Misano World Circuit
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza Maggiore
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Stadio Renato Dall'Ara
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria





