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Vacation home rentals in Casentino

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Top-rated vacation home rentals in Casentino

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Top guest favorite

A spacious living room features an archway of exposed brick and stone, with large windows allowing natural light. A comfortable sofa is positioned around a coffee table, while a professional kitchen is visible in the background, complemented by wooden shelves filled with books.

Vacation home in Arezzo

5 out of 5 average rating, 137 reviews

Historic Arched Apartment in the Heart of Arezzo

In the old town centre of Arezzo, next to Casa Vasari, rises up the sixteenth century building, owned in the past by the Ubertini family. A few steps away from all the attractions of the city, the old kitchens of the building have been transformed into an elegant and comfortable guesthouse, rich in charm in every detail. The interior design is well-finished and, making every detail stand out, is finely furnished with traditional carpets and antique pieces. Locanda Bellavita is an apartment for up to 7 people, on the ground floor with an independent entrance. It consists of two master bedrooms, one French bedroom, one restroom with bath and another one with shower, a big living room with a massive fireplace, dining room and professional kitchen. ingresso privato,tutti gli ambienti sono in esclusiva Salvo alcuni giorni della settimana,abito sopra la struttura The apartment is in a building in the old town center of Arezzo next to Casa Vasari. It’s a few steps from all the attractions in the city. a 100mt dalla Chiesa di san Domenico e dal Duomo. Vicinissimo al parcheggio Petri,sotto il Duomo della città. In 5 minuti ovunque a piedi nel centro della città In the middle of the old town centre the guesthouse is a few steps away from every touristic attraction. The apartment is entirely exclusive for you for the period reserved and is provided with every comfort. The kitchen is professionally equipped. The towels and bed linen will be changed every 4 days. To prepare breakfast, there is an area with coffee machine, kettle, toaster and microwave. *The rooms will be naturally chilled thanks to the thick stone walls, so you won’t need any air conditioning.

An aerial view captures a charming Tuscan farmhouse nestled within lush green vineyards and rolling hills. The property features a rustic stone exterior and a terracotta roof, complemented by surrounding greenery and a clear blue sky.

Vacation home in Poggibonsi

4.95 out of 5 average rating, 175 reviews

Vittoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

A modern kitchen space features a marble countertop with two wooden stools. Large windows showcase a scenic view of Florence's rooftops, including the iconic dome, while natural light fills the room. A fruit bowl and coffee maker are included on the counter.

Vacation home in Florence

4.96 out of 5 average rating, 421 reviews

Breathtaking view from romantic nest in citycenter

Unique and charming attic in the middle of historic center with amazing breathtaking view on the city center. Perfect for a romantic stay in the heart of Florence. Fully windowed on 3/4 walls. Completely renewed with modern design furniture. Powerful A/C, fast wi-fi, fully equipped kitchen. Going downstairs you will immediately be absorbed in the most beautiful area of city center. Attention! Only for young-soul people: 5th FLOOR, NO LIFT, last 2 flights of stairs in a narrow spiral stair.

A scenic view is presented, featuring a wooden structure nestled within lush greenery. A private hot tub is visible in the foreground, accompanied by lounging chairs and a sunshade. The outdoor area showcases a well-maintained path leading to the entrance of the round accommodation.

Vacation home in Reggello

4.89 out of 5 average rating, 137 reviews

The Florentine Barrels

Bellissima botte abitativa completamente fatta in legno, la botte è una delle più grandi al mondo 3,5 metri di diametro per 8 metri di lunghezza. Dispone di cucina, ampio bagno ,spaziosi armadio e comodo letto. La botte è situata in una tenuta agricola in Toscana nel mezzo di una bellissima oliveta . Massima tranquillità con vista mozzafiato e idromassaggio. Zona molto strategica per visitare le migliori città toscane, come Firenze, Siena e Arezzo . Esperienza fantastica e rilassante.

Top guest favorite

An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.

Vacation home in Sovicille

4.97 out of 5 average rating, 145 reviews

Podere La Castellina - N°1 COTTAGE

Cottage indipendente in pietre e mattoni all'interno del "Podere la Castellina" (ex convento 13° secolo), nel magnifico parco naturale della Montagnola Senese. Il cottage può ospitare comodamente 5 persone e comprende: - ampio soggiorno con tv e camino - cucina abitabile con forno - camera matrimoniale - camera con tre letti singoli - bagno con doccia A disposizione degli ospiti piscina panoramica, solarium e terrazza con vista mozzafiato, dotata di forno a legna e barbecue.

A stone archway leads into a historic entrance, flanked by rugged walls covered with greenery. The pathway, lined with a metal railing, guides visitors through a tranquil setting enhanced by the natural surroundings.

Vacation home in Cortona

4.94 out of 5 average rating, 267 reviews

La casina sulle Mura (with garden and spa jacuzzi)

La Casina è situata nella parte alta di Cortona, nella zona denominata "il Poggio". Si puo' giungere in auto fino al suo ingresso. Il Centro citta' e' raggiungibile a piedi in pochi minuti, percorrendo strade e vicoli caratteristici. Gode di una splendida vista su Cortona e la Valdichiana. E' facile parcheggiare nelle vicinanze. Gli ospiti che giungono in treno in una delle stazioni vicine, su richiesta, possono essere prelevati e accompagnati a destinazione.

The rustic stone facade of the house features abundant greenery and wisteria blooms cascading from the upper balcony. The entrance is accessible via a stone pathway, and wooden beams frame the windows, enhancing the traditional Tuscan architecture.

Vacation home in San Martino Sopr'Arno

4.94 out of 5 average rating, 112 reviews

Casa Manu

CARATTERISTICA CASA TOSCANA in pietra immersa nelle colline della provincia di Arezzo. Vicino a Siena, Firenze, Cortona, Perugia, Sansepolcro e alle Foreste Casentinesi. Ideale per trekking, turismo enogastronomico (a pochi km si trovano alcune tra le migliori cantine della Toscana), per appassionati di arte e cultura. A disposizione esclusivamente per gli ospiti un grande terrazzo panoramico, molto riservato. Vi accoglieremo con un presente di benvenuto.

An ancient stone farmhouse with a rustic red-tiled roof is surrounded by lush greenery. The building sits within a mountainous landscape, framed by trees. The open sky above reveals soft clouds and sunlight, hinting at the serene atmosphere of the rural environment.

Vacation home in Chiusi della Verna

4.96 out of 5 average rating, 138 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.

A swimming pool with a wooden deck is framed by lush greenery, providing a backdrop of rolling hills in the distance. An outdoor shower is positioned beside the pool, and the clear water invites relaxation under a partly cloudy sky.

Vacation home in Dimezzano

4.89 out of 5 average rating, 301 reviews

[Authentic StoneHouse] Garden & Viewpool Apartment

Authentic, quiet and cozy entire Stonehouse situated in a medieval small village, with stunning view pool on the top of the garden overlooking hills and vineyards, wide garden, many resting areas, stone-bbq and Pizza oven. Few Km away from Greve in Chianti, about 30 minutes from Florence and Arezzo, 45 minutes from the horse-ride city of Siena. Typical tuscany restaurant and wineries within 5 minutes by car.

A charming rustic farmhouse is set against a dramatic sky, framed by lush green trees. The exterior features warm-toned walls and a tiled roof, while a spacious yard includes seating arrangements for outdoor relaxation, inviting guests to enjoy the serene countryside.

Vacation home in Simignano

4.93 out of 5 average rating, 197 reviews

Casa al Gianni - Quercia

Ciao, siamo Cristina & Carmelo! Vi invitiamo a vivere un’esperienza autentica nel nostro agriturismo “Casa al Gianni” situato 20 min da Siena. Il nostro marchio è la vita semplice a stretto contatto con la natura e gli animali della nostra fattoria. Immerso tra i boschi e la splendida campagna toscana trascorrerai una vacanza indimenticabile. Questo angolo di paradiso ti rimarrà nel cuore!

A cozy bedroom features a spacious bed adorned with yellow cushions, alongside a wooden desk with a stylish chair. Natural light filters in through large wooden windows, offering a view of greenery outside. The warm tones of the exposed brick wall complement the room's inviting ambiance.

Vacation home in Florence

4.84 out of 5 average rating, 358 reviews

La Gabbia del Grillo <Anna Maria> (A-04)

The apartment, located in the historic center, is located in a private internal courtyard overlooking the Duomo. You can use tables and chairs outside to relax and enjoy a unique view. In the bedroom and in the living room there are large wooden windows that make the apartment very bright; the parquet floors and the colors of the walls create a welcoming and relaxing atmosphere.

An outdoor area is presented, featuring a stone-paved patio with several potted plants. The entrance to the house is framed by arched doors, which open to a cozy seating arrangement. Views of the surrounding landscape are visible in the background.

Vacation home in Faella

4.93 out of 5 average rating, 118 reviews

Appartamento storico Il Prato a Castelfranco

Il Prato è una casa colonica storica toscana alle porte di Castelfranco di Sopra, finemente restaurata e circondata da olivi, frutteti e boschi. Ha un bellissimo giardino con piscina dove poter rilassarsi e mangiare. Equidistante dalle grandi città d'arte di Siena, Firenze e Arezzo.

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Popular amenities for Casentino vacation home rentals

Free parking on premises

Air conditioning

Family-friendly vacation home rentals

Top guest favorite

A bright bedroom features a spacious bed with crisp white linens and a decorative pillow. A vivid landscape painting hangs above, while a window with wooden frames reveals a scenic view of the Tuscan hills, complemented by soft natural light filtering through sheer curtains.

Vacation home in San Gimignano

4.98 out of 5 average rating, 127 reviews

Respira la Toscana: vista a 180° sulle Colline

A renovated stone farmhouse is set against a sunset backdrop, showcasing warm tones. The structure features a balcony and arched entryway, surrounded by greenery. A paved pathway leads to the entrance, with rolling hills visible in the distance.

Vacation home in IT

4.85 out of 5 average rating, 73 reviews

Fantastic vieuw House

Top guest favorite

A comfortable living area features a stone fireplace, surrounded by traditional furnishings. Light from table lamps casts a warm glow in the space. Large windows offer views of the outdoors, and terracotta flooring complements the rustic wooden beams overhead.

Vacation home in Umbertide

5 out of 5 average rating, 21 reviews

Casa Monte

Top guest favorite

A spacious living area showcases a vintage wooden cabinet adorned with intricate designs, paired with modern furnishings. A flat-screen TV is mounted on the wall above the cabinet. Soft lighting from stylish pendant lamps creates a cozy ambiance. Windows reveal a glimpse of the cityscape.

Vacation home in Florence

5 out of 5 average rating, 31 reviews

Penthouse in Great Location with View

Top guest favorite

A spacious kitchen area features wooden beams overhead and a marble stove. A dining table set with tea cups and green plants invites guests to enjoy meals. Wall-mounted artwork and shelves display various decorative items, enhancing the room's rustic charm.

Vacation home in San Gimignano

4.92 out of 5 average rating, 247 reviews

Appartamento Margherita Tuscan home

A serene biolago is set within a lush green landscape, featuring clear water and natural stone edging. Surrounding lounge chairs provide a relaxing space to enjoy views of the distant trees and hills, all under an expansive blue sky with scattered clouds.

Vacation home in Poggibonsi

4.94 out of 5 average rating, 62 reviews

App.Cavallo - Megognano,2/A

A large swimming pool is surrounded by well-maintained grass and gently swaying trees. Sun loungers are positioned along the pool's edge, complemented by white umbrellas. The rustic building in the background features a mix of windows and greenery, adding to the serene outdoor setting.

Vacation home in Barberino Tavarnelle

5 out of 5 average rating, 6 reviews

Glicini 1, holiday home and pool 30' from Florence

Top guest favorite

A tranquil swimming pool reflects the soft colors of the sunset, framed by lush greenery and a neatly manicured lawn. Lounge chairs are positioned around the pool, offering a serene view of the surrounding countryside.

Vacation home in Montespertoli

5 out of 5 average rating, 13 reviews

Casa Vacanze Rondini Blu - Appartamento Uva

Vacation home rentals with a patio

An outdoor area is visible, featuring a wooden deck surrounded by lush greenery and softly landscaped hills. A glass-enclosed dining area is positioned on the deck, which includes a large table and chairs. Trees and decorative stones add to the tranquil ambiance.

Vacation home in Greve in Chianti

4.95 out of 5 average rating, 81 reviews

Casa Sangiovese con mini-piscina in centro a Greve

A two-story villa features a warm yellow exterior, adorned with green shutters and large balconies. A stone pathway leads to the entrance, surrounded by landscaped gardens with various plants and outdoor decor. The structure is complemented by tall cypress trees and a clear blue sky.

Vacation home in Florence

5 out of 5 average rating, 5 reviews

Firenze‼️ Intera Villa in collina 7 posti 4 bagni

The exterior of Casa Turan is framed by lush greenery and vibrant foliage. A stone wall partially encircles the property, which features a curved glass entrance. The building showcases traditional architectural elements with climbing vines enhancing its charming appearance.

Vacation home in Sinalunga

4.8 out of 5 average rating, 15 reviews

Romantisch huisje met jacuzzi en grote tuin - 2p.

Top guest favorite

A dining area is featured with a rustic wooden table and two modern chairs, set against a stone accent wall. A cabinet displays dishware, enhancing the room's character. Soft lighting from an overhead pendant illuminates the space, providing a cozy setting.

Vacation home in Passignano sul Trasimeno

5 out of 5 average rating, 16 reviews

Cottage mit Seeblick-Lea

The exterior of a charming stone country house is displayed, surrounded by lush greenery. A well-maintained lawn leads to a terrace with a wooden table and chairs. Climbing plants adorn the facade, and large windows allow natural light to brighten the interior.

Vacation home in Certaldo

4.94 out of 5 average rating, 18 reviews

La Selva , Country house, 130 mq, Stunning views

The historic farmhouse is surrounded by tall, ancient cypress trees and lush greenery. A gravel patio with outdoor seating is visible in the foreground, leading to an inviting garden area. The sky is clear with scattered clouds, creating a bright and welcoming ambiance.

Vacation home in Radda in Chianti

4.97 out of 5 average rating, 36 reviews

Tuscany Country House, Central Chianti, Top Views

Top guest favorite

A spacious room showcases a large bed against a backdrop of earthy tones and original brick ceilings. Natural light filters through a glass door leading to an outdoor space. A wooden table with a decorative vase is positioned nearby, and a well-equipped bathroom is visible in the background.

Vacation home in Bagno A Ripoli

4.92 out of 5 average rating, 37 reviews

Monolocale in collina a due passi da Firenze

Top guest favorite

A scenic view from a terrace showcases manicured gardens filled with vibrant flowers. A wrought iron fence provides a boundary, while the surrounding lush greenery and rolling hills create a peaceful backdrop. A clear sky extends beyond, highlighting the serene atmosphere.

Vacation home in Arezzo

5 out of 5 average rating, 8 reviews

il Roncolino -house exclusive use in countryside-

Vacation home rentals with a washer and dryer

A dining table is set with plates, cutlery, and glassware, accompanied by a bottle of olive oil. In the background, a cozy seating area can be seen, with a sofa and a staircase leading to a loft, while natural light filters through a set of doors.

Vacation home in Laterina

4.77 out of 5 average rating, 13 reviews

Appartamento con piscina e ristorante

Top guest favorite

The outdoor area features a well-maintained grassy landscape with young olive trees dotting the scene. In the background, two rustic stone buildings are visible, surrounded by lush greenery and trees. A clear blue sky with scattered clouds provides a serene backdrop.

Vacation home in Figline e Incisa Valdarno

5 out of 5 average rating, 48 reviews

Casa colonica nel verde con piscina Solatìo

Top guest favorite

Double doors open to a terrace area with a table and umbrella. The outdoor space is surrounded by greenery and sunlight filters through, providing a welcoming setting for dining or relaxation.

Vacation home in Florence

5 out of 5 average rating, 28 reviews

La Casina di Silvia (app. con terrazza), Firenze

A serene outdoor scene captures a sparkling swimming pool set against a backdrop of lush greenery and flowering plants. The elegantly landscaped garden, featuring stone walls, complements the rustic architecture of the Tuscan farmhouse visible in the distance.

Vacation home in Scandicci

4.8 out of 5 average rating, 40 reviews

Appartamento "VERDE" 2/5 persone, piscina,giardino

A dining setup is presented on a terrace, featuring a neatly arranged table with glasses and plates. The scene is enhanced by a sunset that casts warm light over the surrounding hills and trees, creating a peaceful outdoor dining atmosphere.

Vacation home in Siena

4.97 out of 5 average rating, 66 reviews

Apartment in historic Villa in Siena_"LE CONTRADE"

A spacious living area is highlighted by large windows, allowing natural light to fill the room. Elegant furnishings include a comfortable gray sofa, a round dining table with four chairs, and a cozy reading nook, creating a welcoming atmosphere for relaxation and socializing.

Vacation home in Florence

4.91 out of 5 average rating, 289 reviews

Melarancio Residence

A stone-paved courtyard features a rustic house with weathered yellow walls and green shuttered windows. A small table with chairs is set under the sun, surrounded by potted plants, creating an inviting outdoor space for guests to enjoy the fresh air.

Vacation home in Fiesole

4.85 out of 5 average rating, 66 reviews

[Colline Firenze] Borgo Le Palaie

A sun-drenched pool area features a sparkling swimming pool surrounded by terracotta tiles. A sun lounger and an umbrella provide shaded seating, while a wooden barrel with two glasses and a wine bottle is positioned nearby, creating a serene outdoor atmosphere.

Vacation home in Lilliano

4.89 out of 5 average rating, 9 reviews

Cosy house with private pool

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