
House holiday rentals in Casentino
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Top-rated house rentals in Casentino
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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.
FamilyValueView
4.99 out of 5 average rating, 113 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
ValueFamilyAir conditioning
4.88 out of 5 average rating, 201 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.
FamilyValueTV
4.88 out of 5 average rating, 820 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.
FamilyLocationCheckout
4.95 out of 5 average rating, 103 reviews
Country house with view (NO Jacuzzi)
The house has a private garden of 100 square meters with a tub usable with a depth of 60 cm. Two squares usable for your relaxing and fun, from admire the view, and space for eat outside. WI-FI free. The interior is distributed over two floors: on the first large living room with fireplace, SmartTV, eat area, kitchen and room with pizza oven (there are 2 sofa/bed). On the second floor there are 3 bedrooms, 2 of which are doubles and 1 with a bunk bed and 1 bathroom.
LocationFamilyQuiet
4.87 out of 5 average rating, 122 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.
FamilyLocationView
4.9 out of 5 average rating, 133 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.
FamilyLocationQuiet
4.96 out of 5 average rating, 101 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.
ValueLocationHot tub
4.99 out of 5 average rating, 318 reviews
Casa Rosmarino Eco-Wellness Country Home
Price includes: - Infrared Sauna - Wood for Fireplace - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Treats during your stay Pool & parking lot are shared areas. We have 6 units for rent Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.
FamilyLocationAmenities
4.99 out of 5 average rating, 271 reviews
Villa Lolù with private heated swimming-pool
Charming villa with private heated pool, and outdoor hot tub. Very large 175 sqm house with kitchen, dining room, living room with fireplace, 3 double bedrooms, 1 bedroom with 2 single beds, 1 double sofa bed, 3 bathrooms, one of which is en suite. Starting this year, there is also a gym
ValueLocationBarbecue
4.97 out of 5 average rating, 159 reviews
Romantic cosy flat - Toscana Italy
Very quiet village, without shops but sometimes a baker, a haberdasher or a greengrocer come to the village and sell their products, as it used to be decades ago- nice experience! In front of the B&B you can see a small church from the end of the 1800s, with a bell tower. :)
FamilyLocationGetting around
4.99 out of 5 average rating, 100 reviews
Podere I Rovai-apt IL RIFUGIO-in the heart of Tuscany
At the top of the hill, with spectacular views (540.00 meters above sea level), Il Rifugio is a 17th century Tuscan-style apartment located inside the Podere I Rovai complex, in the heart of Florentine Tuscany, surrounded by olive groves, immersed in the green.
FamilyLocationWi-Fi
4.92 out of 5 average rating, 156 reviewsPopular amenities for Casentino house rentals
House rentals with a pool

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
ValueFamilyAir conditioning
4.98 out of 5 average rating, 144 reviews
PoggiodoroLoft, Tuscan dream e relax
FamilyLocationHospitality
4.87 out of 5 average rating, 164 reviews
Il Vecchio Mulino
FamilyLocationKitchen
4.91 out of 5 average rating, 114 reviews
Country House w/ heated Pool near the City Centre
FamilyLocationBathroom
4.82 out of 5 average rating, 158 reviews
La Nipitella Old Barn House, Florence
ValueLocationShared spaces
4.84 out of 5 average rating, 289 reviews
Ancient Tuscan Rural Residence
FamilyLocationBarbecue
4.85 out of 5 average rating, 122 reviews
Explore Chianti from a Charming Stone House
FamilyLocationCondition
4.98 out of 5 average rating, 122 reviews
Villa Podere Cerretino
FamilyLocationGetting around
5.0 out of 5 average rating, 66 reviewsWeekly house rentals

Charming converted Hayloft overlooking the Chianti Hills
ValueLocationQuiet
4.97 out of 5 average rating, 305 reviews
Podere Chiappasonno
FamilyLocationWalkability
4.93 out of 5 average rating, 92 reviews
Typical Tuscan villa - immersed in nature
ValueLocationBreakfast
4.96 out of 5 average rating, 51 reviews
Casa Carla
LocationFamilyDecor
4.99 out of 5 average rating, 92 reviews
Villa dei Macchini
LocationFamilyTV
5.0 out of 5 average rating, 15 reviews
historical townhome in Poppi
FamilyLocationAir conditioning
4.98 out of 5 average rating, 54 reviews
The house in the paradise of Serra.
LocationValueAccuracy
4.86 out of 5 average rating, 43 reviews
Casale del Vino
LocationValueRiver
4.94 out of 5 average rating, 80 reviewsPrivate house rentals

La Pietraia Agritourism
LocationFamilyView
5.0 out of 5 average rating, 5 reviews
beautiful farmhouse in the Chianti region with panoramic garden
FamilyLocationComfort
4.96 out of 5 average rating, 47 reviews
Casa Ciappi
FamilyLocationHiking
4.94 out of 5 average rating, 54 reviews
luxury villa in centre of tuscany
FamilyLocationParking
4.77 out of 5 average rating, 99 reviews
Villa in the forest
LocationFamilyWalkability
4.75 out of 5 average rating, 4 reviews
Villa with Private Pool in the Tuscan Countryside
ValueLocationBathroom
5.0 out of 5 average rating, 21 reviews
Villa Carla – Florence View, Tennis & Hot Tub
LocationFamilyCondition
5.0 out of 5 average rating, 14 reviews
Villa Beatrice with Exclusive Garden
LocationFamilyDecor
5.0 out of 5 average rating, 9 reviewsDestinations to explore
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- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Pinarella Di Cervia
- Mirabilandia
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Mugello Circuit
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- Mercato Centrale
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
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- Piazza della Repubblica
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- Del Chianti
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- Pitti Palace
- Boboli's Garden





