Vacation rentals in Ascianello

4.95 out of 5 average rating, 216 reviews

The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.

Villa in Montepulciano

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

A dining area features a wooden table adorned with a bowl of fruit, complemented by woven seating. Large glass doors open to a terrace, revealing a view of rolling hills and an evening sky, enhancing the indoor-outdoor connection.

4.97 out of 5 average rating, 392 reviews

A view from the top, Montepulciano

A View From the Top is an apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 2 double rooms, 2 bathrooms with shower and a large kitchen-living room with a small terrace overlooking the hills From summer 2025 our wine tasting will be available in the new garden and we have a young private chef for cooking class at home ,not in the weekend. Guests will park close the apartment,in the street 50 mt away.

4.95 out of 5 average rating, 140 reviews

A pergola adorned with blooming wisteria provides shade over a dining area, featuring a round table and red chairs. The vibrant flowers cascade elegantly, enhancing the outdoor space, with the large swimming pool and lush green lawn visible in the background.

Villa in Montepulciano

A paradise in Montepulciano...

Villa Il Cubo is a full centralized air conditioned private house with large private swimming pool placed in the best garden spot for incredible views on the countryside around. Decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY!!!!!!

4.95 out of 5 average rating, 138 reviews

Apartment in Laviano

Farmhouse with swimming pool with wonderful view

Farmhouse Santa Margherita is a splendidly restored 18th century house that sits on a hilltop on the Tuscan-Umbrian border in sight of Montepulciano.The farmhouse has been recently renovated in order to offer to its guests eight vacation apartments. The rooms are very spacious and comfortable. The furnishings are luxurious and include wooden furniture, wrought iron beds and elegant lamps. The kitchens are well equipped so that all your culinary skills can be exercised.

A panoramic view is captured from a window, displaying a vibrant landscape of terracotta rooftops transitioning into verdant hills. In the distance, a charming church steeple rises above the picturesque town, set against a bright blue sky with scattered clouds.

4.99 out of 5 average rating, 261 reviews

Montepulciano Downtown Storico

Nice 60 sqm apartment located in the main street of the village. It is located on the second and last floor of a historic palace. The entrance is located on the main street of the town while the windows overlook the outside of the walls offering a breathtaking view. Apartment consists of: entrance hall, living room with double sofa bed, bedroom, kitchen, bathroom with roof window. It is equipped with microwave, large oven, dishwasher, washing machine and wi-fi.

A charming terrace offers a spacious dining setup, complete with a table set for breakfast. The table displays various breakfast items, and the surrounding views feature terracotta rooftops under a clear blue sky, adding to the inviting atmosphere of this outdoor space.

4.92 out of 5 average rating, 123 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. Immersed in the charming labyrinth of cobblestone streets, you will be greeted by the reassuring sound of bell towers announcing the passage of time, while the inviting scent of freshly baked bread mixes with the aromatic notes of our vineyards.

Apartment in Monticchiello

A charming two-story villa is set amidst a spacious green lawn, surrounded by trees and shrubs. The building features red shutters and a welcoming porch that invites relaxation. Scenic countryside views extend beyond the property, enhancing the tranquil setting.

4.97 out of 5 average rating, 151 reviews

Casa Bonari - a paradise for the eyes

Casa Bonari is a single-level independent apartment inside a villa at the foot of Monticchiello. It consists of 3 bedrooms, 2 bathrooms, an equipped kitchen and a living room. The rooms are bright and furnished in Tuscan style, with old restored family furniture combined with contemporary elements. The kitchen is fully equipped and the apartment is surrounded on all sides by a large garden, so that all rooms boast a beautiful view of the countryside.

An inviting entrance showcases a rustic wooden door, leading to a stone pathway lined with greenery. Open shelves display white dishware and a small flower arrangement, complementing the earthy tones of the surrounding walls.

4.83 out of 5 average rating, 99 reviews

Il Segreto di Agnaresi, 30 meters from Caffè Poliziano

Welcome to the beating heart of Montepulciano, where your stay becomes an unforgettable experience. Our newly renovated apartment, designed to accommodate two people, is located in the center of town, just 200 meters from Montepulciano's majestic Piazza Grande, one of the most beautiful squares in Italy, and only 30 meters from the famous Caffè Poliziano, Montepulciano's most historic bar and the third most beautiful bar in Italy.

Condo in Castelnuovo dell’Abate

A balcony is adorned with blooming flowers and greenery, offering a scenic view of the rolling hills and vineyards. Small outdoor furniture is positioned for relaxation, while the sky features scattered clouds, enhancing the tranquil atmosphere of the surrounding landscape.

4.91 out of 5 average rating, 285 reviews

La Casetta di Brunello, very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

4.96 out of 5 average rating, 348 reviews

A view of the entrance to a countryside property is presented, featuring a gravel driveway that meanders through lush greenery. Tall cypress trees line the pathway, while olive trees and rolling hills create a serene backdrop under a partly cloudy sky.

Condo in Asciano

Romantic Yellow apartment in Crete Senesi

Apartment consisting of 1 comfortable double bedroom, equipped kitchen, living room and bathroom. TV, BBQ, (if needed, we have a washing machine available in our laundry room). A car is recommended as we are in the middle of the countryside, so you can be self-sufficient and visit the magnificent Tuscan countryside as well. Free parking and wifi. I look forward to showing you the real Tuscany!

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Other great vacation rentals in Ascianello

Apartment in Centro Storico

A small balcony features a round glass table set for two, accompanied by two wooden chairs. A view of charming green-shuttered buildings and the historic stone wall is visible, creating a serene outdoor space.

4.96 out of 5 average rating, 226 reviews

Art Apartment Luxury Por Santa Maria

AmandaRating, 5 stars1 day ago

Gorgeous apartment, great location! Beds are so comfortable too!

Superhost

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

4.9 out of 5 average rating, 182 reviews

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

Farm stay in Roccatederighi

An independent stone cottage is surrounded by greenery, featuring a terracotta patio framed by a pergola. The cottage showcases wooden beams and green shuttered windows, with a gentle slope leading to the lush garden and distant trees.

4.92 out of 5 average rating, 132 reviews

Holiday in antique farm, Belvedere

JadeRating, 5 stars1 week ago

We had an amazing week here! The surroundings were absolutely beautiful and our little cottage was super cosy and peaceful. Giulia welcomed us personally and gave us lots of great recommendations for things to do in the area which we really appreciated. Her sister Elisa was also really friendly and helpful. We would love to come back and stay here! It’s a great base for exploring Tuscany and a fantastic place to relax. Thanks so much!

4.98 out of 5 average rating, 111 reviews

Loft in Scandicci

Wonderful Loft in Villa with Pool in Chianti

LorneRating, 5 stars1 day ago

Really enjoyed our stay Chiara’s place. The view from the patio and the pool is spectacular. This was such a nice break from the busy hustle of the cities and one of the highlights of our trip to Italy. Would recommend this spot to anyone who wants to get away for a day or two.

Superhost

Home in Monteroni d'Arbia

4.87 out of 5 average rating, 191 reviews

The Tower of Corsanello

PeterRating, 5 stars2 weeks ago

This accommodation has a really nice view. The bedding was clean and the bathroom was clean. There are two swings, a playground with a slide, a garden, and the kids were happy with animals such as mountain rabbits, cats, mountain birds, snails... etc. I was grateful that the hosts were so kind and sweet. I recommend this accommodation that I want to go to again.

5 out of 5 average rating, 13 reviews

A sunlit stone archway opens into a scenic view of rolling hills. The path, paved with rectangular stones, leads into the distance, framed by aged brick and stone walls. A vintage lamp hangs beside the entrance, adding architectural interest to the alley.

Home in San Gusmè

The Coast

MichaelRating, 5 stars1 week ago

Can’t speak highly enough of elivra and her friends. So helpful and fabulous. Elivra you are a real champ and wonderful person. If airbnb awarded gold medals to their hosts you’d have a drawer full Thank you Michael and Fiona