Apartment holiday rentals in Monticiano

4.92 out of 5 average rating, 194 reviews

Pieve di Caminino Historic Farm

Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.

4.97 out of 5 average rating, 152 reviews

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

A terrace showcases a small table set with glasses and a bottle, complemented by two chairs. A scenic view of the Tuscan countryside can be seen in the background, revealing rolling hills and traditional rooftops under a bright sky.

4.99 out of 5 average rating, 167 reviews

San Miniato - Panoramic terrace in the historic center

Brand new apartment in the historic center of San Miniato. Recently renovated, it is ideal for those seeking tranquility in the heart of the city, with a beautiful view of the Tuscan countryside thanks to the panoramic terrace perfect for a breakfast in the sun or a special aperitif. Immersed in the historic part of the city, typical restaurants, shops and all the beauties of San Miniato can be easily reached on foot. Thanks to its central location, it is ideal for visiting all of Tuscany.

A spacious piazza is surrounded by elegant medieval architecture, featuring a central hexagonal area with open-air seating. Stone pathways lead to various shaded spots, while umbrellas provide shelter for patrons. Beautiful clouds drift overhead, enhancing the vibrant scene of daily life in the historical center.

5 out of 5 average rating, 148 reviews

Piazza Grande Boutique Apartment

Affacciato sulla più bella piazza del centro storico di Arezzo, dove si svolge la rievocazione della Giostra del Saracino, il Piazza Grande Boutique Apartment è situato al secondo piano di un palazzo medievale, con vista sui bellissimi palazzi e le Logge Vasariane ed è una location unica nel suo genere. L'arredamento, opera della contessa Cesaroni Venanzi è stato realizzato con bellissimi mobili antichi reinterpretrati in chiave moderna ed arricchiti da contaminazioni contemporanee.

A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.

4.94 out of 5 average rating, 178 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Superhost

A small wooden table set for two is adorned with fine china cups and a delicate flower vase. The balcony offers a panoramic view of the rolling hills, as the sun sets, casting warm hues over the landscape.

4.91 out of 5 average rating, 284 reviews

I Tramonti di Eramo, central Montepulciano.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

An aerial view captures the extensive grounds of the agriturismo, showcasing a swimming pool surrounded by tall cypress trees and lush green fields. The rustic buildings are nestled among the natural landscape, with rolling hills visible in the background.

4.86 out of 5 average rating, 110 reviews

Appaloosa - Apartment for couples and families

Appaloosa apartment accommodates 4–5 guests and offers air conditioning, Wi-Fi and direct access to the panoramic swimming pool. Ideal for couples or families looking for a relaxing stay in the Tuscan countryside. On the ground floor there is a kitchen, living area, a twin bedroom and a bathroom with shower. Upstairs, reached by a spiral staircase, is the double bedroom with an additional single chair bed.

An outdoor dining area is surrounded by lush greenery and flowering plants, featuring a circular table with four elegant wrought iron chairs. A cozy blanket is draped over one chair, and a scenic view of rolling hills extends in the background under a muted sky.

4.94 out of 5 average rating, 280 reviews

"Red Rose" apartment with view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, each with an independent entrance and private garden, with a panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

An outdoor terrace offers seating for four, featuring a table and chairs. The view captures the skyline illuminated against a twilight backdrop, showcasing notable landmarks such as the Torre del Mangia and the Duomo in the distance.

4.89 out of 5 average rating, 182 reviews

Terrace with a view of Siena

A fianco della Basilica di San Domenico, a pochissimi passi dal Duomo e da Piazza del Campo, in questo splendido ed elegante attico potrete godere della splendida vista e della comodità di raggiungere a piedi in pochi minuti tutti i maggiori punti di interesse della città.

An aerial view of the historic ex-convent showcases its rustic architecture surrounded by lush Tuscan countryside. The property is framed by pathways and green fields, revealing manicured gardens and trees. Nearby roads lead into the tranquil landscape, emphasizing the serene setting.

4.9 out of 5 average rating, 110 reviews

Via Senese, Monteriggioni, Siena

“La Senesina” - Enchanting apartment immersed in the exquisitely beautiful Tuscan countryside, 4 km from Siena and 8 km from Monteriggioni. Ideal location from which to explore the most important towns and cities, rich in history, art and culture.

A rustic dining area features a spacious table set with plates and glassware, surrounded by wooden chairs. Exposed beams highlight the ceiling, while a soft lamp provides gentle illumination. A glimpse of the outside view can be seen through the window, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 219 reviews

Tuscany on the terrace, downtown Montepulciano

Welcome to Montepulciano, the hidden gem of Tuscany, where historical charm blends harmoniously with natural beauty. Our Airbnb in the heart of the historic center embodies the elegance and authenticity of this region.

A bright living area features a comfortable sofa and a wooden dining table adorned with a bowl of fruit. A window offers a view of the surrounding landscape, while decorative artwork and a lamp enhance the space's character.

4.95 out of 5 average rating, 481 reviews

Diacceto19 Siena Apartments Int.2

One of the two splendid apartment ( Int.1-Int.2 ), situated in one of the most beautiful areas of the historic center, decorated in good taste, with an exceptional view and just a few steps from the Piazza del Campo

Popular amenities for Monticiano apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

A panoramic view reveals rolling hills adorned with vineyards and olive groves, stretching under a dramatic sky. The tan-coloured buildings of the property are nestled among lush greenery, while a serene pool reflects the surrounding landscape.

4.98 out of 5 average rating, 62 reviews

Tuscany jem: The Chianti Farmer's House

A window offers a scenic view of the rolling hills and lush greenery of the Tuscan countryside. A round wooden table is set with plates and glasses, complemented by wicker placemats, creating an inviting dining area under soft morning light.

5 out of 5 average rating, 35 reviews

Casa Billi

The historic villa is surrounded by lush greenery, featuring well-maintained gardens and numerous trees. The architecture reflects centuries of history, with a stone tower visible in the background. The structure incorporates large windows that enhance the natural light entering the home.

4.96 out of 5 average rating, 71 reviews

Penthouse in small medieval castle near Florence

A serene terrace space is presented, featuring a round glass table surrounded by white iron chairs. Greenery and blooming flowers are placed in terracotta pots, complemented by a trellis above providing shade. A charming view of terracotta rooftops and clear blue sky is visible in the background.

5 out of 5 average rating, 53 reviews

Live Like a Local & Private Concierge Service

An open-concept living area is presented, featuring a hanging chair and stylish black furnishings. Arched doorways lead to the dining space, which is brightened by natural light. Potted plants add greenery to the environment, alongside a cozy rug on the tiled floor.

4.99 out of 5 average rating, 80 reviews

Herons Superior Apartment - Splendid view!

A bright living area features a cozy blue sofa adorned with patterned cushions. A wooden dining table is positioned nearby, with four chairs available. Shelves on the walls hold various items, and windows are present, allowing natural light to fill the space.

4.91 out of 5 average rating, 54 reviews

small apartment

An outdoor dining area is set beneath a pergola adorned with grapevines, offering a scenic view of the surrounding hills and valleys. A table is arranged with dinnerware, surrounded by metal chairs, creating an inviting space for meals while enjoying the landscape.

4.92 out of 5 average rating, 79 reviews

Podere Belsogno

A rustic kitchen features exposed wooden beams and warm wooden cabinetry. A dining table is set for four, complemented by a well-equipped countertop. Large windows provide natural light, and an inviting entrance leads to the outdoor area. Decorative elements include a chandelier and wall art.

4.97 out of 5 average rating, 62 reviews

Energy: "Cellar in the tuff"

Private apartment rentals

A spacious living area is depicted, featuring a neutral-toned wall with exposed wooden beams above. A coffee table holds a vase filled with colorful flowers, and light floods in from an archway leading to another room. A cozy sofa adds to the inviting ambiance.

5 out of 5 average rating, 46 reviews

Apt 4: Montepulciano 800 yr old Monastery

Flat in Monteleone d'Orvieto

An indoor pool is surrounded by rustic stone walls and a vaulted brick ceiling. Soft lighting enhances the tranquil ambiance. A shallow section of the pool is visible, along with steps leading to another area. Cozy cushions are placed nearby, inviting relaxation.

4.96 out of 5 average rating, 84 reviews

Elegant historic Palazzo, views of Tuscan valley

Superhost

The image displays a large stone villa surrounded by lush greenery and trees. A shared swimming pool, framed by loungers and shaded gazebos, sits in the foreground. In the background, the historic villa can be seen atop a hill, suggesting a picturesque setting in the countryside.

4.93 out of 5 average rating, 15 reviews

Luxury Panoramic Apartment Villa di Radi

A small balcony features two white folding chairs and a table adorned with a vase of green leaves, two glasses, and a bowl of apples. A panoramic view of rolling hills and distant mountains is visible in the background, with a gentle sky emerging at dusk.

4.78 out of 5 average rating, 55 reviews

Romantic cottage with panoramic view

An outdoor dining area features a large table set for four under a spacious umbrella. Two lounge chairs are positioned nearby, surrounded by stone pavers and potted plants. The charming facade of the villa can be seen in the background, enhancing the peaceful ambiance.

4.96 out of 5 average rating, 93 reviews

Villa Medici Donnini Deluxe Apartment

A rustic stone house is set on a small hill, with a gated entrance leading to a gravel path. Lush green trees frame the entrance, providing shade and a natural canopy. The scene is bathed in warm sunlight, enhancing the inviting surroundings.

4.78 out of 5 average rating, 78 reviews

Casa Nati - The Fireplace

An elegant hallway features high ceilings, with art adorning the white walls. A patterned rug lies on the terracotta floor, complementing wooden furniture. Large windows at the end allow natural light to illuminate the space, while a glimpse of the outdoor view is visible.

5 out of 5 average rating, 92 reviews

Luxury Penthouse with Incredible View & A/C 300mq

A bright living area features a comfortable orange couch and a wooden dining table set for two with wine glasses. Large windows provide ample natural light, showcasing views of the surrounding landscape. A flat-screen TV and air conditioning are also present.

5 out of 5 average rating, 72 reviews

Authentic Italian Apartment with Private Terrace

Apartment rentals with a hot tub

An outdoor jacuzzi is situated within a landscaped garden, surrounded by lush greenery. Two lounge chairs are placed nearby on the well-maintained grass, offering a relaxing space to enjoy the countryside views. A large umbrella provides shade over the jacuzzi.

4.89 out of 5 average rating, 71 reviews

Three-room apartment with courtyard for 4 people 5 min. from the center Yes

A bright living area features a wooden table with a wine bottle and glass in the foreground. Large glass doors open to a patio, revealing countryside views and two outdoor chairs facing the tranquil landscape.

5 out of 5 average rating, 24 reviews

Podere Ferranino #Cimabue Townhouse

An inviting entrance features wooden doors framed by rustic stone walls. A small wooden table with two chairs is positioned beside it, adorned with potted flowers. A traditional ceramic jar adds character, enhancing the welcoming atmosphere.

4.96 out of 5 average rating, 46 reviews

SerenaHouse

5 out of 5 average rating, 17 reviews

Vicolo Porte 21/23, Massa Marittima, Jacuzzi

Superhost

A tranquil pool area is surrounded by lush vegetation and stone pathways, inviting relaxation during the evening hours. The soft illumination from surrounding lights reflects off the water, highlighting the pool's inviting turquoise hue and enhancing the calm ambiance of the property.

4.89 out of 5 average rating, 142 reviews

Apartment Alex - Tuscany Charme

A spacious outdoor area features a framed view of rolling green hills in the distance. A swimming pool is visible, surrounded by grass, with a sunshade above a table and chairs. The peaceful landscape showcases the natural beauty of the Tuscan countryside.

5 out of 5 average rating, 42 reviews

Beautiful Sunset Apartment

A bright living area features large windows with soft curtains, allowing natural light to fill the space. A light-colored sofa is positioned against a wall, complemented by wooden chairs and a small dining table. A decorative shelf adds a touch of character to the room.

4.97 out of 5 average rating, 413 reviews

Suite Michelangelo with Terrace

An ancient stone well is positioned in the foreground, showcasing intricate carvings and a circular top. In the background, an impressive stone building features a tower and windows, accented by flags. The scene captures the historical charm of Montepulciano's central square under a clear blue sky.