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Vacation home rentals in Montalcino

Find and book unique vacation home rentals on Airbnb

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Popular amenities for Montalcino vacation home rentals

Family-friendly vacation home rentals

Guest favorite
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, 45 reviews

La Pergola | Farm House with fantastic view

AlbertoRating, 5 stars9 months ago
It was a second stay that lived up to the first. The house has charm, character and comfort. The terrace and garden are beautiful places surrounded by trees and flowers and offer extraordinary views. The area allows for various visits, starting with Cortone with its streets and squares, its churches and museums are worth several visits. The hospitality of Irene and her parents, Fiorella and Luciano, is most friendly.
Superhost
A clear blue swimming pool is framed by blooming flowers and lush greenery. Loungers and umbrellas line the poolside, providing ample space for relaxation. Rolling hills and a serene landscape are visible in the distance under a bright blue sky.
Vacation home in Pian di Marte
5 out of 5 average rating, 3 reviews

Farmhouse near Passignano sul Trasimeno

SerenaRating, 5 stars9 months ago
Wonderful place to escape the city. A heartfelt thank you to the owners Antonella and Francesco, for their availability and humility, wonderful people. We'll definitely see you again. Denis Serena Christian Aurora & Holly
Guest favorite
A small living area features a wooden ceiling with exposed beams. A daybed adorned with patterned cushions sits against the wall. A vintage lamp provides soft illumination beside the daybed, accompanied by a decorative arrangement of sunflowers and a traditional area rug on the floor.
Vacation home in Cortona
4.88 out of 5 average rating, 253 reviews

Wonderful Casa Idilio Cortona

CiaraRating, 5 stars1 week ago
Ah Casa Idilio. A refuge, a feeling of home, a place to recharge, a haven. From the kindness and generosity of Simone and his mother Laura to the intentional and beautifully decorated space itself to the glorious terrace with many well tended plants, this place was truly perfetto. Less than a minute walk to get to cafe bars, little shops, and restaurants. Yet the space itself has a quiet charm, as if it’s far from the center of town, even though it is so close. Great kitchen with all you need to cook and create meals on days you want to stay in. Simone was caring and attentive, offered great ideas for things to do and places to see. He has a very kind sincerity about him and is available just enough! As a woman traveling alone, I felt very safe staying in Casa Idilia for nearly two weeks. I will plan to stay here again when I return to beautiful Tuscany one day. Highly recommend!! Grazie Mille, Simone!!
Guest favorite
The stone farmhouse is set amongst vibrant greenery and blooming flowers, showcasing a blossoming tree in front. The entrance is framed by the surrounding landscape, with a subtle path leading to the door, inviting guests to explore the rustic charm of the property.
Vacation home in Casole d'Elsa (SI)
4.9 out of 5 average rating, 221 reviews

Studio in Tuscan farmhouse with pool & views

DavidRating, 5 stars3 months ago
Thank you Fabio. We have really enjoyed our stay.
Top guest favorite
An aerial view captures the layout of the Podere La Castellina, surrounded by lush greenery. The stone buildings and pathways are visible, alongside a serene swimming pool. Shared outdoor spaces, including seating areas, are interspersed among the natural landscape, promoting relaxation and connection to nature.
Vacation home in Sovicille
4.97 out of 5 average rating, 141 reviews

Podere La Castellina - No. 1 COTTAGE

CatherineRating, 5 stars6 months ago
Daniele and Simone’s place in Tuscany is beautiful. It is such a peaceful and pretty setting with amazing views particularly from the lovely terrace. Our cottage was perfect for our family of four. Comfortable beds and everything we needed. We explored some of the villages nearby as well as wineries and restaurants recommended by Simona which were excellent. We would love to have stayed another night.
Top guest favorite
A charming red house is visible, framed by lush greenery and a neatly trimmed hedge. The entrance features a wooden door surrounded by white shutters. A small porch with a few steps leads to the front door, enhancing the inviting appearance of the home.
Vacation home in Montespertoli
4.95 out of 5 average rating, 135 reviews

Tuscan Orchard

FabiolaRating, 5 stars2 weeks ago
I loved the house! It was so beautiful, cozy and clean. I will definitely book it next time I am in Montespertoli. Fiammetta and Leonardo were very sweet!
Guest favorite
The rustic farmhouse is framed by a stone wall, featuring a pathway leading to a stairway entrance. Lush greenery and flowering plants are visible along the edges, complementing the natural setting. The warm tones of the stone structure contrast with the clear blue sky.
Vacation home in Castelnuovo Berardenga
4.9 out of 5 average rating, 68 reviews

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

ThereseRating, 5 stars7 months ago
Arnaldo's home was wonderful!!! It was perfect for three couples. With private entrances to each apartment, we could all have our privacy but also gather together in the larger downstairs apartment or around the pool. Lorenza was very responsive, even though she was in Portugal when we arrived. She made sure her father and mother were there to show us around and even opened the gate remotely for our friends who arrived a day later than us so we could begin exploring the area and didn't have to be there when they arrived. The villa is beautiful and was exactly as described. We LOVED our time there--a perfect place to celebrate our 50th wedding anniversary!
Superhost
A stone statue is positioned near a private pool, surrounded by greenery and flowering plants. The pool reflects the blue sky, while tall trees frame the view of the lush landscape beyond. The scene offers a serene atmosphere in a secluded outdoor space.
Vacation home in Arezzo
4.71 out of 5 average rating, 48 reviews

Ancient stone farmhouse with park and pool

JessicaRating, 5 stars1 month ago
We had a wonderful stay at Stella’s farmhouse. The grounds and surroundings were excellent for walking and exploring in the mornings and late afternoons. The accommodations very comfortable for our multigenerational family. Stella was an excellent host! Very kind, helpful with all our questions, and provided us some nice recommendations for the region. We would love to return!

Vacation home rentals with a patio

Guest favorite
Vacation home in Greve in Chianti
4.95 out of 5 average rating, 65 reviews

Sangiovese house with mini-pool in the center of Greve

GeorgiaRating, 5 stars2 days ago
We had a wonderful time at Alessandro’s place. It was the perfect location for a five night holiday, close to a supermarket, many Tuscan towns, and wineries! We found ourselves dining at Alessandro’s restaurant daily too, super delicious meals and drinks.
Guest favorite
An aerial view of the farmhouse complex highlights multiple buildings surrounded by lush greenery and olive trees. A swimming pool is visible, along with well-maintained pathways and expansive fields extending into the distance. The serene landscape reflects the charm of the Umbrian countryside.
Vacation home in Cantagallina
4.95 out of 5 average rating, 40 reviews

Il Cipresso, one-bedroom apartment near Trasimeno!

MaudRating, 5 stars1 week ago
Nice place in the middle of the nature. Nice location for cyclists. The host was very friendly and flexible with check in/out times. The house was absolutely beautiful and well equipped. Thanks for the lovely stay.
Superhost
Bright red flowers are seen in terracotta pots alongside a stone wall. Sun loungers with blue fabric are arranged nearby, offering a view of the lush greenery surrounding the area. Natural light filters through the scene, enhancing the vibrant colors of the plants.
Vacation home in Piegaro
4.67 out of 5 average rating, 3 reviews

il Forno - 2-bedroom poolside

MortenRating, 5 stars9 months ago
we had an amazing time in piagaro,and Thomas gave so mutch information about the Village and a guide around when we arrived. that was really good. he was also a really interesting and reflected man. We had some really good conversations and I would love to come back to his place. I used the cafe every morning for the morning coffee just to take in the atmosphere in the village with the most lovely staff there . LOVELY 😃. truly a special stay for us. we wish them the very best 🥰 Morten with family
Guest favorite
A clear view of a private salt-water pool is presented, bordered by wooden decking. Two lounge chairs are positioned nearby under a large umbrella. Lush greenery surrounds the area, complemented by a stone barbecue and covered dining space in the background.
Vacation home in Monticiano
5 out of 5 average rating, 36 reviews

Casa Dani with private pool

LeasaRating, 5 stars7 months ago
Beautiful accomodation and very clean. Loved that we could walk into town for essentials and to eat and drink. Pool and outside area is stunning . Dani helped when we needed coal and was on hand for help. The accomodation has absolutely everything you need in the kitchen as well as hair dryer, towels for bathing and pool, extra pillows and blankets . We would absolutely recommend.
Guest favorite
A large swimming pool is surrounded by lush greenery and olive trees. Rolling hills and vibrant vegetation are visible in the background, creating a serene outdoor space for relaxation. Sun loungers are positioned around the pool, inviting guests to enjoy the scenic views.
Vacation home in Campagnatico
4.85 out of 5 average rating, 13 reviews

Cozy Cottage with a beautiful view - Casa Luciano

ThomasRating, 5 stars4 weeks ago
We had a very nice time at Casa Luciano! Unfortunately, we could not use the great pool in March (although ice bathing is becoming more and more popular ;-)). The area is very nice and quiet. We were able to hike, explore Campagnatico and other places. Once we were able to enjoy the good food in Vecchia Oliviera. (Attention: Pizza is only available from about May) We also supported the village shop properly. It has a decent selection for its size. Thanks Mel for the always timely support with questions and problems! We will recommend the accommodation and maybe we will also manage to vacation here during the pool season.
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
4.97 out of 5 average rating, 63 reviews

Fontarcella, H&R- mediterranean home with jacuzzi

עפריRating, 5 stars1 week ago
The stay was excellent, thinking about the little details, great kitchen and activities equipment The host was in touch with us all the time and responded quickly to any questions and gave recommendations on what to do in the area Everything was clean and tidy and very beautiful, great value for the price!
Guest favorite
The sleeping area features a spacious bed adorned with a patterned blanket and decorative pillows. Natural light filters through curtained windows, illuminating the room. A wardrobe and shelves provide storage, and the wooden flooring adds warmth to the space.
Vacation home in Figline Valdarno
4.86 out of 5 average rating, 90 reviews

Vacation home Il piccolo rifugio

ClaireRating, 5 stars5 days ago
We had a lovely stay at Annalisa's. She had nice touches for us and we thank her. She is also very responsive.
Guest favorite
A living area features a light blue couch adorned with decorative pillows. A glass coffee table sits in front of the couch, complemented by a vase of fresh flowers. A vintage wooden dresser adds elegance to the space, with natural light entering through a wooden-framed window.
Vacation home in Panicale
4.92 out of 5 average rating, 12 reviews

Il Pollaio guests house

ScottRating, 5 stars2 weeks ago
We enjoyed 3 nights in this beautiful home. Everything in the home was lovely and we wish we could have stayed longer. We met with Elisa and she shared some local recommendations for us which we greatly appreciated. She also left us a lovely bottle of wine which was very thoughtful. Although Panicale is small, we felt right at home immediately. We loved that you could walk to two little cafes and several amazing restaurants. We enjoyed two wonderful meals in Panicale and our morning coffee and pastry at one of the small cafes. We loved this location and explored several other small Italian villages which were close by. We enjoyed talking to some of the locals and learning more about this charming town. Our stay at Elisa's was very nice and we had everything we needed. We hope to come back.

Vacation home rentals with a washer and dryer

Guest favorite
An aerial view of the rustic property reveals a serene landscape featuring a pool surrounded by greenery. The casale sits amidst sprawling fields and olive groves, with winding paths leading through the natural surroundings, providing a sense of tranquility and space.
Vacation home in Chianciano Terme
5 out of 5 average rating, 88 reviews

The Eagle and the Olive Tree

Michael RobertRating, 5 starstoday
Amazing place to spend time. Great hosts and fantastic location
Top guest favorite
Vacation home in Figline e Incisa Valdarno
5 out of 5 average rating, 40 reviews

Farmhouse in the countryside with swimming pool Solatìo

FilippoRating, 5 stars4 days ago
Amazing stay! The house was beautiful, stylish, and super comfortable. The location couldn’t have been better—close to everything but still peaceful. Truly worth the visit. Would absolutely come back!
Top guest favorite
The image captures a lush landscape framed by a rustic stone window. Rolling green hills and scattered trees extend into the horizon, under a clear blue sky. The view conveys the serene beauty of the surrounding Tuscan countryside.
Vacation home in Monteroni d'Arbia
4.9 out of 5 average rating, 68 reviews

White lily with a view of Siena

CarolineRating, 5 stars1 week ago
This was the second time we stayed in one of Marta‘s apartments! I think that says it all already. We are just in love with the location and the apartments always make you feel at home right away! Thank you again Marta for hosting us (and the delicious vino 🍷😄). We will be back 100%!
Guest favorite
A serene swimming pool is surrounded by well-maintained grass and lounge chairs with umbrellas. The tranquil water reflects the green hills in the distance, creating a calm environment for relaxation. The area is designed for shared enjoyment, providing ample space for sunbathing.
Vacation home in Vitignano
5 out of 5 average rating, 27 reviews

Podere Vittoria Apartment: Heart of Chianti

WinnieRating, 5 stars1 week ago
we had such a wonderful time at Tuscany and a lot of it was because of this airbnb. this place has such a serene garden and backyard space and it's awesome to be so close to nature. Edoardo was extremely helpful and welcoming making this place homey. most of the times I asked a question and got an answer from him in seconds. I'd love to take my family back and stay here again.
Guest favorite
Two lounge chairs are positioned on a grassy area in a private garden, surrounded by potted plants. Tall trees provide shade and a natural backdrop, contributing to a tranquil outdoor space.
Vacation home in Sorano
4.81 out of 5 average rating, 100 reviews

Da Simona

AlbertoRating, 5 stars7 months ago
Cleanliness, courtesy and professionalism, Simona is the perfect host! Very nice and comfortable accommodation to reach the main places of interest in the area.
Guest favorite
A charming villa is surrounded by lush greenery and features a sloped, tiled roof. Two white umbrellas provide shade over outdoor seating areas, while a gravel pathway leads through the inviting garden towards the scenic hillside in the background.
Vacation home in Siena
4.9 out of 5 average rating, 40 reviews

Apartment in historic Villa in Siena_"IL MANGIA"

YuRating, 5 stars1 month ago
This was such a wonderful experience, enjoyed the beautiful courtyard for 4 days, clean rooms, quaint and textured furnishings and set up, it does have a warm home feel.Many times I want to be lazy in the room, enjoy the sunshine of the courtyard, and enjoy all the amenities provided in the room.I highly recommend this homestay, take a bus at the door for a few minutes to the ancient city of Siena, we go up each time to the ancient city on foot, you can enjoy the pastoral scenery of Tuscany all the way, thank you Cristina and her brother for their warm and thoughtful service, and the opportunity to come back here later.
Superhost
A view of a charming medieval square surrounded by historic stone buildings, featuring a canopied area with potted plants. Clothes hang drying from a window, while the sky is filled with clouds and streaks of blue, enhancing the inviting atmosphere of the village.
Vacation home in Colle di Val d'Elsa
4.72 out of 5 average rating, 29 reviews

Tower House of the 1000

GabrieleRating, 5 stars5 days ago
Host available and kind, the house is located in Colle Alta and is not equipped with an elevator and also reaching Colle Alta is not very easy because it is very uphill. But there is a breathtaking view and the location is right in the center. The apartment is equipped with two bathrooms and a washing machine, dishwasher and dryer. We had a great time.
Top guest favorite
A charming medieval cellar is presented with stone walls and a combination of modern design elements. A sleek counter with a sink is placed against one wall, complemented by soft lighting that enhances the historical character of the space.
Vacation home in Sorano
4.95 out of 5 average rating, 21 reviews

Palazzo Palloni Boutique Apartment

Luis GuillermoRating, 5 stars2 weeks ago
Mario and Mateo their son are 10/10 are aware of everything, that one feels at home, the accommodation is INCREDIBLE, it is in the center so you don't need anything else, you can go out to walk it,

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Montalcino
  6. Vacation home rentals