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Apartment vacation rentals in Monticiano

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Quick stats about apartment rentals in Monticiano

  • Total vacation rentals

    Explore 20 vacation rentals in Monticiano

  • Nightly prices starting at

    Monticiano vacation rentals start at G$10,460 GYD per night before taxes and fees

  • Verified guest reviews

    Over 400 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Wi-Fi availability

    10 of Monticiano vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Monticiano rentals

  • 4.8 Average rating

    Monticiano stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated apartment rentals in Monticiano

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

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Top guest favorite
An aerial view captures the agriturismo surrounded by lush green fields and a neatly arranged row of tall cypress trees. The inviting pool reflects the serene landscape, and the winding dirt road leads towards the property, nestled amid the picturesque Crete Senesi.
Apartment in Asciano

Loggia 1 in farmhouse with shared pool

Apartment for 2 people in the Santa Lucia farmhouse (farmhouse DIVIDED IN 7 APARTMENTS) in the Crete Senesi, 10 km from Siena. Located on the second floor with a private table in front of the windows of the entrance loggia. It consists of a double bedroom (two single beds joined to form a double bed), a bathroom with shower and a living room with functional kitchen. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room FOR A FEE according to consumption.

4.97 out of 5 average rating, 185 reviews
Top guest favorite
A scenic view captures a lush landscape with rolling hills, vineyards, and olive trees under a colorful sunset. The traditional Tuscan casolare is visible in the background, surrounded by greenery, while the horizon features soft hues of orange and pink.
Apartment in Poggibonsi

Laura Chianti Holidays

Laura Chianti Vacanze is the ideal solution for those seeking peace and tranquility immersed in the Chianti countryside. The apartment is halfway between Florence and Siena, and is conveniently located for quick access to Florence, Siena, San Gimignano, Volterra, as well as the beautiful Chianti hills. The apartment offers private parking, two bedrooms, a fully equipped kitchen, private bathroom, private garden, barbecue, and a wonderful view of the Chianti hills.

4.98 out of 5 average rating, 338 reviews
Top guest favorite
A rustic stone farmhouse is surrounded by colorful flower pots, adding charm to the entryway. The structure features a mix of wooden shutters and terracotta accents. A gravel driveway leads to the entrance, framed by lush greenery and vibrant blooms.
Apartment in Castiglione d'Orcia

Mimosa Apartment - Poggio al Vento

Private apartment in a farmhouse from the 1600s. The same consists of kitchen, double bedroom and bathroom. It has everything you need for a pleasant stay. From the terrace, the breathtaking view, overlooking Mount Amiata, Rocca D'Orcia an ancient fortress and the Castle of Ripa D'Orcia. The swimming pool overlooks the Montalcino side. We are an organic farm, we produce high quality wine and oil. We offer, for a fee, tastings of our red wines. Winery tour etc

4.99 out of 5 average rating, 112 reviews
Top guest favorite
The lounge features elegant walls adorned with intricate frescoes and moldings. A large mirror reflects the refined decor. Two white armchairs and a colorful sofa provide seating, while a coffee table rests on a patterned rug before a decorative fireplace.
Apartment in Siena

Luxury frescoed apartment in the historical center

The Palazzo Pannilini Superior apartment is composed of a bright entrance enriched by an elegant coffered ceiling, a large fully frescoed lounge, a large foyer, a kitchen equipped with a terrace, a dining room topped with a frescoed vault, four bedrooms, three bathrooms, a wardrobe room, and a panoramic terrace where you can sunbathe and relax. The apartment is located at the second floor with no elevator. The apartment has air conditioning.

4.98 out of 5 average rating, 113 reviews
Top guest favorite
An aerial view reveals the rustic stone farmhouse surrounded by lush greenery and vineyards. The inviting pool is set within a well-maintained garden, complemented by outdoor seating and barbecue areas, offering a peaceful retreat in the heart of the Tuscan countryside.
Apartment in Gavignano

Poggio Massiccioli

Cozy apartment for 4 people furnished in Tuscan style and with exposed beams immersed in the rolling hills of the Tuscan countryside. Guests have access to a furnished garden, free Wi-Fi, a shared swimming pool, a wood-burning oven, a barbecue, and a washing machine. The apartment was converted from a charming 19th-century stone farmhouse, recently renovated in the Tuscan tradition and divided into three comfortable apartments.

4.92 out of 5 average rating, 386 reviews
Guest favorite
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.
Apartment in Buonconvento

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.

4.86 out of 5 average rating, 122 reviews
Top guest favorite
A spacious terrace is shown, featuring comfortable seating arrangements, including lounge chairs and a small dining table. The area is partially shaded by awnings, with a view of the surrounding landscape. A table is set with fresh strawberries and beverages, inviting relaxation.
Apartment in Siena

Terrace on the walls of Siena - Casa Laura

Elegant apartment in the center of Siena with a large terrace, 600 m from the stadium and 1 km from Piazza del Campo. Located on the 4th floor (elevator up to the 3rd), it offers 2 double bedrooms, 2 bathrooms, an equipped kitchen, air conditioning in every room and a beautiful panoramic terrace above the historic walls. In the limited traffic zone. Perfect for experiencing Siena in comfort!

5.0 out of 5 average rating, 104 reviews
Top guest favorite
The outdoor pool area features a light blue water surface complemented by three tiered fountains. A small white table with a glass is placed on the wooden deck, surrounded by two white chairs. The rustic stone buildings create a charming backdrop, adorned with greenery.
Apartment in Montalcino

Castel Brunello - 2 doublebed rooms + terrace

Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.

4.99 out of 5 average rating, 117 reviews
Guest favorite
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.
Apartment in Monteroni d'Arbia

"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).

4.94 out of 5 average rating, 287 reviews
Guest favorite
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.
Apartment in Siena

Terrace with a view of Siena

Next to the Basilica of San Domenico, a few steps from the Duomo and Piazza del Campo, in this splendid and elegant penthouse you can enjoy the splendid view and the convenience of walking to all the major points of interest in the city in just a few minutes.

4.87 out of 5 average rating, 200 reviews
Top guest favorite
A scenic view of the Tuscan hills is framed by clusters of pink roses in the foreground. The rolling landscape features layers of green and gold fields, softly fading into the horizon under a clear sky.
Apartment in Montalcino

Panoramic Country Suite Montalcino

Fonte Aulente is a Tuscan farmhouse from the 12th century recently restored surrounded by beautiful garden-park, 2 km from Montalcino with amazing views on Tuscan hills. We offer a beautifully furnished apartment with independent entrance and all facilities.

4.9 out of 5 average rating, 404 reviews
Guest favorite
A view from the window showcases mist-covered rolling hills and lush greenery. Trees and a rustic building can be seen in the distance, framed by the natural surroundings. The sky displays a soft blue hue, adding to the serene landscape.
Apartment in Asciano

Farmhouse apartment with pool

The apartment has been carefully restored, in keeping with its original character and to create harmony between the exterior and interior. It has a large kitchen/living/dining area with open fireplace. Views of the countryside from every window.

4.9 out of 5 average rating, 103 reviews

Popular amenities for Monticiano apartment rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly apartment rentals

Guest favorite
Apartment in Siena

Claudia's House in Piazza del Campo

4.93 out of 5 average rating, 111 reviews
Superhost
The expansive view of rolling hills is captured under a dynamic sky filled with scattered clouds. The lush greenery contrasts with the golden fields, creating a serene landscape. In the foreground, the garden area is surrounded by rustic pathways and trees, enhancing the natural setting.
Apartment in Asciano

Podere Le Splandole - Crete Senesi

4.89 out of 5 average rating, 365 reviews
Top guest favorite
Two comfortable chairs are positioned on a lush green lawn, complemented by a small wooden table. A basket of vibrant yellow flowers is nearby, set against a backdrop of rolling hills and cypress trees under a clear blue sky.
Apartment in Monticchiello

Casa Bonari - a paradise for the eyes

4.97 out of 5 average rating, 187 reviews
Guest favorite
Apartment in San Gusmè

La Dimora del Luca

4.98 out of 5 average rating, 169 reviews
Guest favorite
A tranquil garden space is visible, featuring a large, white umbrella providing shade over two reclining chairs. Lush green grass surrounds the area, complemented by potted greenery and flowering plants, creating a serene outdoor escape.
Apartment in Siena

Casa Borgianni at Villa Caprera

4.92 out of 5 average rating, 120 reviews
Top guest favorite
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.
Apartment in Monticiano

small apartment

4.92 out of 5 average rating, 62 reviews
Guest favorite
A charming holiday home is set amidst a lush green landscape, surrounded by trees and open fields. The structure features a rustic aesthetic with a tiled roof, and an inviting covered terrace is visible, ideal for enjoying the serene countryside views.
Apartment in Monticiano

Il Fontanino holiday home

4.94 out of 5 average rating, 17 reviews
Top guest favorite
Apartment in Asciano

Incredible Views & Pool in the Tuscan Hills

4.86 out of 5 average rating, 22 reviews

Private apartment rentals

Superhost
Apartment in Montalcino

Wp Relais Argante Apartment

5.0 out of 5 average rating, 4 reviews
Top guest favorite
An outdoor seating area is shaded by a fabric canopy, featuring a comfortable long bench with decorative pillows and a dining table surrounded by metal chairs. Colorful flower pots filled with blooming flowers enhance the garden's vibrant atmosphere, set against a rustic stone wall.
Apartment in Colle di Val d'Elsa

CANONICA 43 Luxury villa in the heart of Tuscany

5.0 out of 5 average rating, 78 reviews
Top guest favorite
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.
Apartment in San Rocco A Pilli

Authentic Italian Apartment with Private Terrace

5.0 out of 5 average rating, 77 reviews
Guest favorite
The image presents an aerial view of a rustic villa surrounded by rolling hills and vineyards. A rectangular swimming pool is situated in the foreground, and the greenery of the surrounding gardens enhances the serene landscape. The property showcases traditional architecture with terracotta roofs.
Apartment in San Gimignano

Il Castro Luxury San Gimignano. Michelangelo Suite

4.81 out of 5 average rating, 64 reviews
Top guest favorite
Apartment in Siena

Apartment with a view in a farmhouse in Siena with Wi-Fi

5.0 out of 5 average rating, 12 reviews
Guest favorite
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.
Apartment in Montalcino

Podere Belsogno

4.93 out of 5 average rating, 88 reviews
Guest favorite
A charming stone facade of a Tuscan house is framed by lush greenery and flowering pots. A small table with chairs invites outdoor seating, while wooden beams support the vine-covered pergola, creating a shaded area. Bright flowers add a touch of color to the rustic setting.
Apartment in Chiusdino

La Pergola: sunny & charming hilltop country house

4.95 out of 5 average rating, 94 reviews
Superhost
A rustic outdoor patio is framed by lush green vines, creating a natural canopy. A large table is surrounded by wooden and wrought-iron chairs, providing ample seating for guests. Sunlight gently filters through the arches of the adjacent building, enhancing the relaxed ambiance.
Apartment in San Giovanni d'Asso

Podere Ferranino #Brunelleschi Townhouse

4.95 out of 5 average rating, 22 reviews

Apartment rentals with a hot tub

Guest favorite
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.
Apartment in Castelnuovo Berardenga

Villa di Geggiano - Perellino Suite

4.94 out of 5 average rating, 183 reviews
Guest favorite
A rectangular swimming pool with a shallow and deep end is surrounded by a stone patio and lush greenery. A villa sits on a hillside in the background, featuring a terrace with windows and shutters. Poolside lights are placed around the pool for evening ambiance.
Apartment in Siena

Villa'Colombaiolo di Marciano', 28

4.9 out of 5 average rating, 146 reviews
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.
Apartment in Sassetta

Apartment Alex - Tuscany Charme

4.89 out of 5 average rating, 144 reviews
Top guest favorite
The living area features a stylish design with a dark gray sofa and two deep red armchairs. A round glass table sits on a marble floor, enhanced by natural light from the two windows with light curtains. A decorative mirror and elegant light fixtures adorn the walls.
Apartment in Siena

Domus Nannini - L'Arco di Matteotti Spa

4.98 out of 5 average rating, 107 reviews
Top guest favorite
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.
Apartment in Montepulciano

Charming House in Montepulciano

4.93 out of 5 average rating, 153 reviews
Top guest favorite
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.
Apartment in Radicondoli

SerenaHouse

4.96 out of 5 average rating, 49 reviews
Top guest favorite
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.
Apartment in Castelmuzio

Beautiful Sunset Apartment

5.0 out of 5 average rating, 54 reviews
Superhost
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.
Apartment in Siena

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

4.87 out of 5 average rating, 86 reviews

Destinations to explore