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Vacation rentals in Montalcino

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Montalcino vacation rentals

Stay near Montalcino's top sights

Valdorcia6 locals recommend
Murlo25 locals recommend
Centro Benessere Le Terme6 locals recommend
Montalcino Fortezza station16 locals recommend
Pienza Cathedral3 locals recommend
Coop12 locals recommend

Other great vacation rentals in Montalcino

Top guest favorite
A private outdoor space features a serene swimming pool surrounded by stone tiles. Comfortable lounge chairs are positioned near the pool. A gazebo provides shade, furnished with seating, and overlooks lush greenery, enhancing the tranquil atmosphere of the area.
Apartment in Mercatale Valdarno
4.98 out of 5 average rating, 80 reviews

Panoramic view from stone Apartment- Pool and A/C

ClaireRating, 5 stars7 months ago
While looking for a place to stay it’s often difficult to choose. If we had known how fabulous this place was it would have been a no brainer! We all agreed that this is the best Airbnb we have ever stayed in on all of our travels. Massimiliano was a delight and so personable. He made excellent suggestions one being having a cooking lesson. If you have a chance ask for Francesca! The BEST! One last thing…we left with amazing recommendations for the next part of our trip. Thank you so much for a wonderful stay! Good luck with the harvest!
Guest favorite
A charming stone exterior features large windows and arched details, surrounded by lush greenery. A path lined with lavender leads to the entrance, with outdoor seating visible under shaded umbrellas. The tranquil setting is complemented by nearby trees and rolling hills in the background.
Cottage in Volterra
4.9 out of 5 average rating, 179 reviews

Podere Grignano, beautiful Tuscany

MarkRating, 5 stars2 months ago
Stefano and Roberta are two of the most absolute intrepid souls you will ever encounter. Their hospitality and generosity is without equal. Smartly appointed and expertly renovated, this exquisite example of an ancient farmhouse sits atop a stunning ridge line with vast views and expansive mountain scenery inspiring and enchanting at every turn. Right in the heart of Tuscany, this spectacular piece of the Italian wonderland does not disappoint!
Top guest favorite
A stone farmhouse is illuminated against the evening sky, showcasing its rustic architecture. Lush green lawns surround the structure, leading to a pool area where lights reflect softly on the water, creating a tranquil ambiance. The surrounding landscape features trees and landscaped gardens.
Apartment in Volterra
5 out of 5 average rating, 10 reviews

MAIN Rustic apartment with exclusive view

VivianaRating, 5 stars4 months ago
Wonderful estate, very kind and helpful host. Too bad we only stayed one day!
Top guest favorite
A spacious outdoor area is showcased, featuring a shared swimming pool surrounded by well-maintained lawns and sun loungers. Umbrellas provide shaded seating, while the scenic countryside extends in the background, enhancing the tranquil ambiance of the agriturismo.
Farm stay in Camucia
5 out of 5 average rating, 7 reviews

The Garden of Olives | Casa Ippocastano

ViktorijaRating, 5 stars7 months ago
Everything was perfect! Nice place to rest with a wonderful chill lounge and a pool. Federica and Enrica were responsive and helpful hosts. Thanks for the time and all the recomendations.
Superhost
A charming stone villa is framed by lush greenery and vibrant flower beds. The building features three arched windows with planters, a terracotta roof, and steps leading to the entrance. The expansive lawn offers a serene atmosphere, complemented by distant views of the rolling hills.
Villa in Radicondoli
4.94 out of 5 average rating, 18 reviews

A Romantic Villa in the heart of Tuscany

AmandaRating, 5 stars7 months ago
We are 2 couples in our early 60s. We adored the home. The surrounds and views sublime. We cooked and loved sitting in kitchen as sun set. Ahhhh. We enjoyed a drink in village at a little store. Our favourite meal was at Nazionale (book or you won’t get in). The lady there is areal character you will get to like her. The agricento restaurant also good. Coop had groceries. The village of Radicondolli is just beautiful. We drove to many places from there. Siena, san Gin, the Terma Antica ….. ( warm mineral waters with spa) nice to be spoilt. Try the other small villages around Radicondoli, we did better than larger ones, like castle d’elsa. Fabulous museum. Our hosts Francesca and Lorenzo were welcoming and met us on arrival. Each room was well separated with ensuite each room. Kitchen fully appointed. Italian coffee pot (buy you ground coffee at coop in town), some basic condiments. Roomy showers, one bath, lots of room to spread out. Herbs in garden.
Guest favorite
A sparkling pool is set in a well-maintained lawn, surrounded by tall trees and cypress plants. Comfortable lounge chairs are positioned beside the water, with a shaded area provided by an umbrella. The rustic villa can be seen in the background against a clear blue sky.
Villa in Asciano
4.95 out of 5 average rating, 76 reviews

Podere on the Crete Senesi

ChulaRating, 5 stars6 months ago
We spent a glorious and relaxing week at Sarchianello and could not recommend it more. The location was perfect for day trips to local places like Siena and Montalcino, and it was the ideal place to return to for an evening of eating and drinking. We loved our stay and were sorry to leave! It truly felt like a home away from home.
The exterior of a single-story villa is shown, featuring pale walls and light blue shutters. A small patio area is visible, furnished with a white chair. Surrounding greenery and tall pines create a natural boundary, emphasizing the quiet and relaxed setting.
Villa in Marina di Grosseto
5 out of 5 average rating, 8 reviews

Villetta Lorenza

AndreasRating, 5 stars23 months ago
Despite very bad weather, we were able to make good use of the time in the house and its surroundings. The kitchen is well equipped and could be cooked well every day. Since our stay was in the preseason, regional restaurants were not open, which was not bad.
Superhost
A tranquil pool area is set against a scenic backdrop of rolling hills, with lounge chairs arranged around the water's edge. Umbrellas provide shade, and steps lead into the inviting blue pool. Lush greenery surrounds the space, contributing to a peaceful outdoor atmosphere.
Villa in San Gimignano
4.58 out of 5 average rating, 12 reviews

Historic watchtower restored Acacia

Sivert AndreasRating, 5 stars21 months ago
We loved it! Tuscany at it’s best!

Quick stats about vacation rentals in Montalcino

  • Total rentals

    920 properties

  • Nightly prices starting at

    $20 before taxes and fees

  • Total number of reviews

    24K reviews

  • Family-friendly rentals

    500 properties are a good fit for families

  • Pet-friendly rentals

    530 properties allow pets

  • Rentals with a pool

    390 properties have a pool

Frequently Asked Questions

  • Are there bed and breakfast rentals with a dedicated workspace in Montalcino?

    Yes! Work meets play with ease at over 10 bed and breakfast rentals in Montalcino featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in apartment rentals in Montalcino?

    Experience the best of Montalcino with our apartment rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly villa rentals in Montalcino?

    Four-legged friends are welcome in Montalcino. Choose from more than 60 villa rentals for guests traveling with pets.

  • Do apartment rentals in Montalcino have a bbq area?

    Absolutely! We offer over 80 apartment rentals with a bbq area in Montalcino. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Montalcino have self check-in?

    Absolutely! We offer over 10 villa rentals with self check-in in Montalcino. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Montalcino have a gym?

    Absolutely! We offer over 10 villa rentals with a gym in Montalcino. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Montalcino have wifi?

    Absolutely! We offer over 60 condo rentals with wifi in Montalcino. Enjoy a tailored experience with all the comforts you desire.

  • Are there Montalcino villa rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 90 villa rentals with pools in Montalcino, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly apartment rentals in Montalcino?

    Montalcino has more than 170 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Bed And Breakfast Rentals in Montalcino?

    Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 60 homes with wifi, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Montalcino