Vacation rentals in Casentino

4.99 out of 5 average rating, 410 reviews

Farm stay in Ruscello

Farmhouse Fattoria La Parita

Provencal style apartment surrounded by vineyard and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 from the highway. The singing of the acorn and cuckoo will be the soundtrack to the living room while the roe deer burn among the olive trees. An Italian basic breakfast (coffee, tea, milk, cookies, etc.) is included, if you prefer a richer and served breakfast at the table, the cost is €10 per person (€6 from 5 to 15 years, free less than 5 years old). Wallbox EV available.

4.97 out of 5 average rating, 285 reviews

A tranquil plaza is featured, flanked by archways and historical stone buildings. The main church displays a simple yet elegant facade with a bell tower. Dim light filters through the clouds, creating a serene atmosphere in the square.

Condo in Asciano

Green – The meadows in Tuscany

Apartment consisting of 1 comfortable double bedroom, equipped kitchen, large living room and bathroom TV, BBQ, (we have a washing machine available in our laundry room for those who request it). We recommend a car as we are in the middle of the countryside, so you can be self-sufficient and visit the magnificent Tuscan countryside as well You will like the outdoor environment because it is magical by day and at night Free parking and WiFi Convenient location to visit both Tuscany and Umbria.

4.88 out of 5 average rating, 176 reviews

A serene view from the infinity pool extends toward rolling green hills under a clear blue sky. The tranquil water reflects the clouds, creating a seamless horizon that enhances the natural beauty of the landscape.

Home in Casale

Infinity view

Completamente ristrutturata posizione con vista mozzafiato sul Valdarno. Il piano terra è composto da soggiorno con due vetrate che danno sul patio, camino, divano letto, bagno con grande doccia e cucina moderna con isola in acciaio, con tre porte finestre per accedere alla zona pranzo esterna con bbq. Il primo piano è composto da due camere matrimoniali ognuna dotata del proprio bagno con doccia. Giardino è moto curato,ci sono vari angoli relax, prendisole è una piscina infinity ad idrolisi

4.91 out of 5 average rating, 110 reviews

A stone terrace is surrounded by lush greenery and potted plants, leading to a rustic structure adorned with climbing vines. Scenic views of the countryside stretch into the distance under a clear blue sky, creating a peaceful outdoor space.

Loft in Poppi

PIPPO'S LITTLE RESORT/2

Immerse yourself in the quiet of Tuscany with the lush green countryside,an unforgettable meals,and the ultimate relax!Pippo's Little Resort/2 is located in the National Park of Casentino,3km away from POPPI with a middle age Castle and local Bio food produced by the local farmers.The loft has been carefully renovated and furnished minimally, using reworked industrial furniture mixed with modern design pieces.Join us this Spring Summer season with a generous glass of wine, great food and more!

4.82 out of 5 average rating, 101 reviews

A medieval stone castle stands against a blue sky, surrounded by green landscapes. Towering cypress trees frame the structure, which features an archway at its base leading into the ruins. The texture of the weathered stone contrasts with soft clouds, adding to its historical charm.

Condo in Rimbocchi

Cozy apartment in stunning National Park forest

This cosy apartment immersed in one of Italy's largest National Parks offers a breath of fresh air. Perfect for hikers - many paths begin direct from the door, ideal for those walking to La Verna. Just a 5min minute walk away are waterfalls and natural pools. In a unique area of the Casentino the tranquil village of Rimbocchi invites you to escape the chaos of urban life. Although remote, it's also a convenient base to visit many historic cultural towns all within an hour by car.

Condo in Castelfranco di Sopra

An aerial view captures a rustic stone building with red tiled roofs, surrounded by lush greenery, trees, and manicured gardens. The serene landscape showcases a blend of earth tones and foliage, embodying a peaceful atmosphere in a hillside setting.

4.83 out of 5 average rating, 249 reviews

House between Firenze, Arezzo, chianti e Siena

The House is located in a restored medieval village. There is an atmosphere of peace and tranquility, the gardens are full of flowers and aromatic plants and there is a beautiful panoramic view of the Arno Valley. There is a private terrace outside and two swimming pools to share with other appartraments. Perfect for relaxing and for reaching the main attractions like Florence, Siena, Arezzo, Chianti, Sangimignano. Here you will live a unique experience in the heart of Tuscany ...

4.99 out of 5 average rating, 266 reviews

An outdoor terrace is visible, furnished with several tables and chairs, providing ample seating. Flower pots with colorful blooms adorn the railing, while a panoramic view of the surrounding hills and greenery stretches into the distance under a clear sky.

Apartment in Sinalunga

Resort Panoramic view - Free parking

Appartamento nuovo , potente Wi-Fi, SMART TV, bagno privato , Aria Condizionata, cucina privata , lavanderia , parcheggio privato gratuito . Sala da tea ad uso gratuito . Vista panoramica mozzafiato . Tra le Crete Senesi e la Val D’Orcia , a 800metri dal centro del paese , con ristoranti , bar e supermercati . Posto strategico per visitare le principali località in Toscana : Montalcino , Pienza , Siena , Arezzo , Rapolano Terme , Montepulciano .

4.99 out of 5 average rating, 124 reviews

Home in Prato

Tofanello Turquoise Luxury 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 orange apartment. Orange: https://www.airbnb.com/rooms/plus/9429730

4.99 out of 5 average rating, 120 reviews

The exterior of a charming stone cottage is presented, featuring large arched windows and a wooden door. Vibrant greenery surrounds the building, with a stone pathway leading to a small outdoor seating area with metal chairs and a table, ideal for enjoying the natural surroundings.

Guesthouse in Perugia

Ethical house in Umbria

It is a 60 sqm annex suitable for couples who want to visit our region. We don't have a swimming pool but we have the truffle ground, the stream, the roe deer, porcupines, wild boars, our cats and the little dog Moti. In the garden, you will find herbs, fruit, and garden produce. Inside the cottage we rent, you will have our olive oil and helichrysum liqueur that we produce. We also produce saffron, but we sell it! Of course, pets are welcome!

Vacation home in Chiusi della Verna

A remote farmhouse is nestled within a vast expanse of lush green forest, surrounded by rolling hills under a cloudy sky. The vibrant red roof contrasts with the dense greenery of the trees, emphasizing the tranquil isolation of this off-grid retreat.

4.96 out of 5 average rating, 135 reviews

Experience rustic off-grid life in the wilderness

This ancient farmhouse lies within a national park in one of the largest areas of forests in Europe. Solar power, wood stoves and the bumpy road offer an authentic off-grid experience. A rare privilege to go into the wild and take a break from urban life and modern conveniences. Hike to the monastery of St.Francis and the sacred forests of La Verna...or simply sit and enjoy the peace of this magical remote place.

4.96 out of 5 average rating, 245 reviews

A serene salt-water pool is surrounded by lush greenery and colorful flowers. Sun loungers are positioned around the pool, offering seating for relaxation. Rolling hills and cypress trees create a picturesque backdrop, showcasing the tranquil beauty of the Tuscan countryside.

Condo in Panzano

Apt. Panzanello-Panzano in Chianti

The apartment offers all the comforts and tranquility of the Tuscan countryside. Enjoy the wonderful view that you can admire from your private terrace, a perfect place to spend peaceful and serene moments accompanied by a good glass of Panzanello wine. Access to the apartment is private and free parking is available. The kitchen is equipped with everything you need to prepare delicious meals.

4.89 out of 5 average rating, 193 reviews

A stone patio is seen outside a rustic building, featuring a table set for two. Lush greenery surrounds the area, including tall trees and shrubs. A tranquil countryside view is visible in the background, contributing to the serene outdoor setting.

Farm stay in Simignano

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Casentino vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Casentino

NinaRating, 5 stars10 months ago

A stone farmhouse is set amid lush green hills, accompanied by an infinity pool reflecting the sky. Sun loungers are arranged by the poolside, and umbrellas provide shade. Steps lead from the grass to the terrace, offering a scenic view of the surrounding landscape.

Villa in Cortona

Podere Cantalena

Wonderful place in calm and tranquil area! The house, pool and garden are beautiful, a real Tuscany dream! The house is rented out via an agency, that manages all the practicalities before arrival, but the hosts live close by and were extremely welcoming! They don't speak English very well, but we managed very well with signs and Google translate. They met us at the house with a platter of local snacks, wine and juice. Inside the house was fresh fruit and their own white wine, honey, olive oil etc. They visited twice during our stay to clean the pool and both times left us presents, the first time a basket of fresh vegetables and eggs, the second time a selection of cakes. When we had trouble with a missing pizzaspade, they came right away. The communication was easy and quick. In conclusion: a completely wonderful stay in the most beautiful surroundings and with the nicest and friendliest hosts! If we ever get the chance, we will most certainly come back!

Apartment in Mercatale Valdarno

4.98 out of 5 average rating, 80 reviews

Panoramic view from stone Apartment- Pool and A/C

ClaireRating, 5 stars8 months ago

While looking for a place to stay it’s often difficult to choose. If we had known how fabulous this place was it would have been a no brainer! We all agreed that this is the best Airbnb we have ever stayed in on all of our travels. Massimiliano was a delight and so personable. He made excellent suggestions one being having a cooking lesson. If you have a chance ask for Francesca! The BEST! One last thing…we left with amazing recommendations for the next part of our trip. Thank you so much for a wonderful stay! Good luck with the harvest!

4.9 out of 5 average rating, 181 reviews

A stone farmhouse is framed by tall cypress trees, with large arched windows and a tiled roof. A grassy area in front includes a seating arrangement, complemented by a backdrop of lush greenery and distant hills under a clear blue sky.

Cottage in Volterra

Podere Grignano, beautiful Tuscany

RobertRating, 5 stars1 week ago

We’ve had a lovely week at Podere Grignano, a haven of peace, tranquility and greenery. It’s isolated, but that’s why we chose the location. The last kilometre of the road is quite rough. Just go slow! You can shop at Volterra, 35 minutes away. No osterias or trattorias nearby. But Podere has excellent cooking facilities so we had a wonderful time preparing and consuming the local produce and wine. Bedroom was spacious and comfortable, bathroom modern and water is hot. Stefano and Roberta are lovely hosts, discrete but helpful- and the owner, Marco, gives you detailed instructions on how to find Podere. The attached cottage is BEAUTIFUL, just as the pictures show. It was spotlessly clean, had lots of little extras: Stefano gave us a bottle of their magnificent olive oil. We spent the week visiting numerous hilltop towns (including San Gimignano, but seriously, there are tiny gems that avoid the tourist hordes.) Love the views, love the accommodation, love the countryside. Come here…

5 out of 5 average rating, 9 reviews

A circular view framed by lush greenery showcases rolling hills under a partly cloudy sky. The vibrant landscape stretches into the distance, highlighting the undulating terrain and distant mountains.

Home in Volterra

Vacation in an authentic farmhouse 10 km from the city

Aditya EmmanueleRating, 5 stars8 months ago

We had a very nice, relaxing stay on Bellavista. Angela and her father were extremely welcoming. We were supplied with our own wine, homemade luggage and farm fruits. Staying on Bellavista was definitely worth it and we'll be in the area again at some point, we'll be back! Wehrli family

4.98 out of 5 average rating, 110 reviews

Loft in Scandicci

Wonderful Loft in Villa with Pool in Chianti

MelissaRating, 5 stars3 weeks ago

We had a wonderful relaxing stay !! The loft was beautiful! The view from the balcony was spectacular! A truly special place …. Thank you

Farm stay in Greve in Chianti

4.87 out of 5 average rating, 194 reviews

The Bartaline Hut

AlexandraRating, 5 stars1 month ago

We had a wonderful stay! The place was very comfortable and had everything. We loved sitting at the table and looking over the valley! Until next time!

4.93 out of 5 average rating, 231 reviews

The hallway features warm lighting from wall sconces illuminating a piece of wall art. A closed door is positioned at the end, while a radiator is visible along the left side. The walls are finished in a soft tone, complemented by wooden beams overhead.

Condo in Florence

Ognissanti 94

BenRating, 5 stars8 months ago

Large airbnb tucked outside the city. Location is very walkable. Space is large, and unit is clean. Marina & her team were very accommodating with us as well, which I appreciate!