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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, 136 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, 420 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.

Top guest favorite

An aerial view captures the historic castle surrounded by lush green hills and vineyards. The impressive structure features tall towers and ornate architecture, set amid manicured gardens and tree-lined pathways, reflecting the beauty of the Chianti landscape.

Vacation home in Badia a Passignano

5 out of 5 average rating, 111 reviews

Chianti Craft House Badia a Passignano

Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area

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, 134 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, 265 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, 111 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, 297 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.

Top guest favorite

The image captures a serene outdoor setting featuring a swimming pool surrounded by a well-maintained lawn. Several sun loungers positioned around the pool invite relaxation, while the rustic house and lush greenery complete the idyllic scene.

Vacation home in Panzano

4.97 out of 5 average rating, 156 reviews

Fienile Santa Teresa

EMERGENCY COVID 19: The barn will be sanitized with products in accordance with the law before each entry, every possible protection will be implemented!!! For a peaceful time immerse yourself in typical rural Tuscan life at this excl. guest barn surrounded by vineyards & olives groves lying between Florence & Siena. Please ask for special offers during the off season and for long term stays!

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

4.94 out of 5 average rating, 194 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!

Vacation rentals for every style

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Popular amenities for Casentino vacation home rentals

Free parking on premises

Air conditioning

Family-friendly vacation home rentals

A rustic wooden table is set in a softly lit room, adorned with a vase of freshly picked wildflowers. A window with wooden shutters provides a view to the outside, allowing natural light to fill the space, enhancing the warm color of the walls.

Vacation home in Terranuova Bracciolini

4.89 out of 5 average rating, 9 reviews

Residenza Borghesi: Accomodation "Caterina"

A charming path winds through lush greenery, leading towards a rustic stone house surrounded by colorful flowers and vines. The scenic landscape features rolling hills and trees, creating a peaceful and inviting atmosphere for guests.

Vacation home in Cortona

4.98 out of 5 average rating, 47 reviews

La Pergola | Farm House with fantastic view

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, 45 reviews

Casa colonica nel verde con piscina Solatìo

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, 125 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, 72 reviews

Fantastic vieuw House

A tranquil outdoor pool is surrounded by lounge chairs set on a grassy area. Lush greenery encapsulates the pool, with olive trees in sight, providing a peaceful natural backdrop against a clear blue sky.

Vacation home in Sogna

4.93 out of 5 average rating, 46 reviews

Sogna in Tuscany -- Nature, Relax & Explore

Top guest favorite

A spacious bedroom features a king-size bed with an intricately designed headboard. Soft lighting from two bedside lamps creates a warm glow. Natural light enters through a window with sheer curtains, offering a view of the greenery outside. A built-in wardrobe is visible in the corner.

Vacation home in Petrignano del Lago

4.98 out of 5 average rating, 90 reviews

Fontarcella, H&R- mediterranean home with jacuzzi

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, 246 reviews

Appartamento Margherita Tuscan home

Vacation home rentals with a patio

A bright bedroom features a spacious bed with light linens and a decorative throw. Natural light enters through open double windows, revealing a private terrace. A television and a small desk with a chair are present, while two bedside tables with lamps offer soft lighting.

Vacation home in Monteroni d'Arbia

4.91 out of 5 average rating, 80 reviews

White lily con vista su Siena

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, 3 reviews

Firenze‼️ -Intera Villa in collina 7 posti 4 bagni

Top guest favorite

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

4.86 out of 5 average rating, 14 reviews

Romantisch huisje met jacuzzi en grote tuin - 2p.

Top guest favorite

An elegant dining area is centered around a large wooden table surrounded by soft, upholstered chairs. Beams of natural light filter through skylights and windows, highlighting the warm wooden ceiling and contemporary kitchen space in the background.

Vacation home in Monteroni d'Arbia

5 out of 5 average rating, 13 reviews

Tuja

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, 17 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, 35 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, 6 reviews

il Roncolino -house exclusive use in countryside-

Vacation home rentals with a washer and dryer

A glass of white wine rests on a stone railing, overlooking a tranquil scene of Lake Trasimeno. Lush green cypress trees frame the view, with the calm waters reflecting the sky’s hues and two distant islands visible in the background.

Vacation home in Passignano sul Trasimeno

5 out of 5 average rating, 28 reviews

Antico Casale Tiravento - App. con balcone

Top guest favorite

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, 65 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, 285 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

4.87 out of 5 average rating, 62 reviews

[Colline Firenze] Borgo Le Palaie

An open-plan living area features exposed wooden beams and large windows allowing natural light to fill the space. Teak furniture, including a seating area and dining table, complements the rustic design. A modern kitchen with stainless steel appliances and a gas cooker is visible.

Vacation home in Sovicille Siena

4.89 out of 5 average rating, 18 reviews

Tuscany country Village near Siena

The outdoor area features a sparkling swimming pool surrounded by lush greenery, tall trees, and comfortable lounge chairs. Umbrellas provide shade, and a stone wall frames the space, enhancing the serene atmosphere of this inviting garden retreat.

Vacation home in Ulignano

4.75 out of 5 average rating, 12 reviews

★ Romantic apartment & stunning view of Tuscany ★

Top guest favorite

A spacious sleeping area features a large bed with soft green pillows and a light blue coverlet. Natural light enters through the sliding doors, which lead to a private courtyard. A circular wall decoration made of foliage adds a touch of nature, complemented by two bedside lamps.

Vacation home in Florence

5 out of 5 average rating, 64 reviews

GREEN like hope in Florence

Top guest favorite

An open living space features a round dining table with seating for four, complemented by a cozy gray sofa adorned with orange cushions. The kitchen area is equipped with modern appliances, including an oven and a microwave. A vibrant sunflower painting adds a splash of color to the wall.

Vacation home in Florence

4.98 out of 5 average rating, 54 reviews

Appartamento Donizetti24 (D24)

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