Cottage vacation rentals in Casentino

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Casentino

Guests agree: these cottages are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1

Guest favorite

An outdoor terrace features a rustic wooden ceiling supported by brick columns. Comfortable seating is provided by a light-colored couch and benches, alongside a dining table with chairs. The surrounding greenery and pathways lead to additional buildings, creating a serene and inviting space.

Cottage in Pergine Valdarno

4.77 out of 5 average rating, 66 reviews

Tuscan countryside vacation home with pool

Exclusive independent house, surrounded by the greenery of the Tuscan countryside near Pergine Valdarno, in the hills of Chianti Aretino between woods, olive trees and vineyards, in the middle of the triangle formed by Arezzo Siena and Florence, on the left bank of the Arno river. Large swimming pool with super panoramic view shared with another apartment. Large fully fenced park. Covered and uncovered panoramic terraces for exclusive use, perfect for lunch and dinner. Large garden. Possibility of trekking bikes.

FamilyLocationPool

Top guest favorite

A dining area features a dark wooden table with black chairs, adorned with a floral centerpiece. Light-colored stone walls and wooden beams create a rustic charm. A blue sofa with floral cushions is positioned against a large window, allowing natural light to fill the space.

Cottage in San Bartolomeo a Quarate

4.92 out of 5 average rating, 157 reviews

FAETOLE typical Tuscan country house near FLORENCE

My cottage is hidden in Tuscan countryside among olive groves, vineyards and woodland. Nevertheless, downtown Florence is only 16km away! While away, spend your time by relaxing in the garden, where you will find a barbecue and an outdoor shower to cool down while sunbathing. Discover the beauty of surrounding countryside with a hike and unwind with a view of picture-perfect vineyards! One can also easily go for day trips to many tiny medieval towns scattered on the hills of Tuscany from here!

FamilyValueNearby

Superhost

A quaint outdoor dining area features a round table with rust-colored cushions and wooden chairs set on a grassy patch. The backdrop includes a charming brick structure with green-framed windows and warm lighting, surrounded by lush vines and greenery.

Cottage in Florence

4.84 out of 5 average rating, 172 reviews

FARMERShouse/casaBARTHEL 15' from the City Center

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.

ValueFamilyParks

Top guest favorite

An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.

Cottage in Geggiano

4.99 out of 5 average rating, 154 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

ValueFamilyHot tub

Guest favorite

Cottage in Castellina in Chianti

4.97 out of 5 average rating, 112 reviews

Cottage Cappero – Masseto In Chianti

MASSETO IN CHIANTI è un villaggio privato dove potrete rilassarvi nel vostro giardino privato e in piscina, fare sport, o utilizzare come base per visitare città rinascimentali: Firenze, Siena, San Gimignano, Arezzo, Volterra. Offriamo altri tre cottage con accesso indipendente e giardinetto privato: Quinto (2 letti), Vittoria (4 letti), Leccio (6 letti). La piscina è condivisa dai 4 cottage, ciascuno dispone di un gazebo privato, con distanze garantite e sanificazione a norma Covid-19.

ValueFamilyShared spaces

Guest favorite

An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.

Cottage in Monteriggioni

4.95 out of 5 average rating, 290 reviews

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

FamilyValueWifi

Guest favorite

A charming outdoor patio area is surrounded by olive trees, featuring comfortable seating arrangements. A stone wall complements the rustic architecture of the cottage, which is partially shaded by a white canopy. The area offers a peaceful view of the lush hillside.

Cottage in Bagno A Ripoli

4.91 out of 5 average rating, 70 reviews

The Cottage Florence

The Cottage Florence .. così si realizzano i sogni. La cornice è dorata, la posizione dominante, centrale, indispensabile a volte per trovarsi emozionalmente sopra alla quotidianità e vivere un ambiente che pone la propria persona ed il proprio spirito come su di un altipiano. Vedere ad occhi aperti il paesaggio e le sensazioni di pace e di controllo che questo evoca con tutto il necessario ed il superfluo a portata di mano dove tutto è panoramico sulla città di Firenze.

LocationFamilyParking

Guest favorite

The exterior of a charming stone cottage features large windows and a distinctive roof design. Surrounding the cottage, a well-maintained garden showcases colorful roses, while seating options are positioned on a stone patio, inviting relaxation amidst natural scenery.

Cottage in Greve in Chianti

4.96 out of 5 average rating, 51 reviews

Very cosy cottage with beautiful views

Very cosy cottage in the heart of Chianti with beautiful views on the Greve Valley.Restored in tipical tuscan style with family furniture and old cotto floor.Wood stairs and wood room floors,upstairs rooms with low ceilings but confortable.Sleeps 5 people,veranda -livingroom ,2 double rooms,1 single room,3 bathrooms,well equiped kitchen with washdisher,oven,4 fire stove. Air-condtioning,exclusive use of the swimmingpool.Walking distance from Panzano in 15-20 minutes.

ValueLocationQuiet

Top guest favorite

The jacuzzi is featured outdoors, illuminated with blue lights, creating a calming atmosphere at night. The surrounding stone walls provide privacy, and a dining table can be seen nearby. Steam rises, indicating the water is warm and inviting.

Cottage in San Casciano In Val di Pesa

4.96 out of 5 average rating, 192 reviews

Il Fienile, Cottage in the country with Jacuzzi

Surrounded by wineyards, close to Florence, a charming accomodation in a cozy cottage with heated jacuzzi at your exclusive use. Perfect starting point to discover Florence and Siena. Kitchen, wide living room, bathroom, two double bedroom (one with an extra single bed). In the living room a sofa bed for other 2 people. Tasteful furniture, Air Conditioning, barbecue, private parking. Partnership for: bike rental, private chef, private driver

LocationFamilyAccess

Guest favorite

The exterior features a spacious garden surrounded by greenery, showcasing a variety of plants. A shaded area provides seating with lounge chairs and a large tree offers additional shade. The house structure is visible in the background, with large windows reflecting the landscape.

Cottage in Castelfranco Piandiscò

4.91 out of 5 average rating, 86 reviews

Villetta Belvedere

The villa is finely renovated, surrounded by greenery, with a large courtyard, garden and woods bordering the property, and with a wide panoramic view of the typical Tuscan landscape. Its strategic location, at the end of a residential cul-de-sac, while surrounded by greenery, allows you to reach, on foot, all the necessary services (market, bars, historic center, pizzeria & restaurants) for a relaxing and comfortable stay.

FamilyLocationHospitality

Guest favorite

The garden features a shaded dining area with a large umbrella and a wooden table set with chairs. A brick barbecue stands nearby, surrounded by greenery and well-maintained grass. The entrance to the house is visible through elegant wrought iron doors.

Cottage in La Piazza

4.96 out of 5 average rating, 127 reviews

Casa La Misura in the heart of Chianti

La Misura house is part of Borgo Montecastelli, a beautiful rural complex located right on the border between the provinces of Siena and Florence. Due to its strategic position, straddling two valleys, Borgo Montecastelli enjoys a magnificent panorama from its summit towards the villages that surround it: Panzano, Radda in Chianti, Castellina in Chianti, as well as farmhouses, churches, and towers.

ValueFamilyDecor

Guest favorite

A charming cottage is surrounded by lush green grass and decorative plants. The rustic brick exterior features large windows framed with climbing vines. A cozy seating area on a tiled porch offers a relaxing view of the garden and the inviting countryside.

Cottage in Montagnano

4.93 out of 5 average rating, 138 reviews

Charming cottage in Tuscany

Charming cottage located on a hill with 360-degree views. An oasis of peace and quiet. Surrounded by greenery. Large swimming pool BBQ Area Inside there is a bedroom with a French bed, a living room with a sofa bed, a bathroom, a kitchenette and an indoor and outdoor dining area. Ideal for couples and families with one/two children. Crib available

LocationValueGrill