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House holiday rentals in Casentino

Find and book unique houses on Airbnb

Top-rated house rentals in Casentino

Guests agree: These houses are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Greve in Chianti
4.99 out of 5 average rating, 114 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.

ValueFamilyPool

Guest favourite
An expansive outdoor deck offers a serene view of rolling hills under a clear sky. An infinity pool transitions seamlessly into the landscape, with two soft seating cushions placed nearby, inviting relaxation and contemplation of the stunning panoramic scenery.
Home in Casale
4.88 out of 5 average rating, 201 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

LocationFamilyCondition

Top Guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home in San Casciano In Val di Pesa
4.98 out of 5 average rating, 243 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.

ValueLocationGetting around

Superhost
A private outdoor space features a Jacuzzi surrounded by stone paving, with the house visible in the background. The two-story structure has wooden windows and doors, creating a welcoming setting. Nearby shrubbery and a tree provide additional greenery and shade.
Home in Stia
4.87 out of 5 average rating, 123 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.

FamilyLocationNearby

Guest favourite
A serene bedroom features a spacious bed with a simple white coverlet. A wooden chair with a striped cushion is placed beside a bench. Natural light filters through the two wooden windows, revealing views of the lush vineyards outside.
Home in Castelnuovo Berardenga
4.9 out of 5 average rating, 133 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.

LocationFamilyHospitality

Top Guest favourite
The farmhouse entrance is framed by two potted plants and orange pumpkins. A stone facade features a wooden door with gray shutters, complemented by a tiled roof. Natural surroundings are visible in the background, emphasizing the peaceful rural setting.
Home in Prato
4.98 out of 5 average rating, 144 reviews

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.

ValueFamilyCondition

Top Guest favourite
An aerial view of the CasaMacchia property, showcasing a traditional stone villa surrounded by lush greenery and mature trees. A private pool is visible within the garden, complemented by terraced areas and colorful flowers. The landscape features rolling hills in the background.
Home in Castelfranco Piandiscò
4.96 out of 5 average rating, 101 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.

LocationFamilyParking

Guest favourite
A spacious freestanding bathtub is filled with water, adorned with floating flowers and candles. A small wooden table beside it holds a bucket of champagne and two glasses. Soft towels and a decorative rose are also visible, contributing to a relaxing ambiance.
Home in Fiesole
4.99 out of 5 average rating, 318 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.

ValueLocationCondition

Top Guest favourite
A rustic living area features a wooden table surrounded by two elegant armchairs and a beige sofa. A stone fireplace, stocked with logs, stands as a focal point, while wooden beams adorn the ceiling. An inviting atmosphere is created by warm, natural colors and soft furnishings.
Home in Anghiari
4.99 out of 5 average rating, 271 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.

ValueFamilyWi-Fi

Superhost
A bright living area features a wooden coffee table at its center, flanked by a light-colored sofa and a darker green couch. Two windows with wooden shutters offer views of the surrounding vineyards, while exposed wooden beams add character to the ceiling.
Home in Greve in Chianti
4.86 out of 5 average rating, 101 reviews

Country Rentals - La Canonica

CANONICA apartment is a portion of an ancient farmhouse located in the heart of the Chianti Classico area. It is surrounded by the vineyards of Villa Calcinaia, estate owned by Capponi Counts since 1524, grown from the four original poderi to an extension of 215 hectares of which 30 are vineyards. The apartment is situated next to the shared pool.

LocationValueHiking

Top Guest favourite
Home in Terranuova Bracciolini
4.97 out of 5 average rating, 159 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

LocationFamilyLaundry

Top Guest favourite
The outdoor pool features clear turquoise water, surrounded by a stone patio. Lush green hills and tall cypress trees create a scenic backdrop, while a few lounge chairs are positioned nearby for relaxation.
Home in Subbiano
4.99 out of 5 average rating, 101 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. :)

ValueFamilyBarbecue

Popular amenities for Casentino house rentals