
Vacation rentals in Montalcino
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Montalcino
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Montalcino vacation rentals
Other great vacation rentals in Montalcino

Panoramic view from stone Apartment- Pool and A/C
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!

Podere Grignano, beautiful Tuscany
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!

MAIN Rustic apartment with exclusive view
Wonderful estate, very kind and helpful host. Too bad we only stayed one day!

The Garden of Olives | Casa Ippocastano
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.

A Romantic Villa in the heart of Tuscany
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.

Podere on the Crete Senesi
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.

Villetta Lorenza
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.

Historic watchtower restored Acacia
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
- Florence Vacation rentals
- Elba Vacation rentals
- Pisa Vacation rentals
- Rome Vacation rentals
- Bologna Vacation rentals
- Cinque Terre Vacation rentals
- Portofino Vacation rentals
- Riviera di Levante Vacation rentals
- Francavilla al Mare Vacation rentals
- Genoa Vacation rentals
- Italian Riviera Vacation rentals
- Verona Vacation rentals
- Kid-friendly rentals Montalcino
- Rentals with an EV charger Montalcino
- Rentals with a fireplace Montalcino
- Luxury rentals Montalcino
- Rentals with breakfast Montalcino
- Rentals with a fire pit Montalcino
- Fitness-friendly rentals Montalcino
- Rentals with a sauna Montalcino
- Vacation home rentals Montalcino
- Bed and breakfasts Montalcino
- House rentals Montalcino
- Pet-friendly rentals Montalcino
- Villa rentals Montalcino
- Rentals with pools Montalcino
- Rentals with a hot tub Montalcino
- Rentals with a patio Montalcino
- Condo rentals Montalcino
- Family-friendly rentals Montalcino
- Apartment rentals Montalcino
- Rentals with outdoor seating Montalcino
- Farmstay rentals Montalcino
- Rentals with a washer and dryer Montalcino
- Cottage rentals Montalcino
- Smoking-friendly rentals Montalcino
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- CavallinoMatto
- Marina di Grosseto beach
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Cavallino Matto
- Santa Maria della Scala
- Casa Barthel
- Cala Di Forno
- Tenuta Le Velette
- Podere La Marronaia, Sosta alle Colonne
- Cala Violina
- Cantina de' Ricci
- Cantina Contucci
- Riva del Marchese
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Cantina Stefanoni
- Madonna del Latte
- Pubblico Palace
- Castiglion del Bosco Winery
- Ugolino Golf Club
- Podere Il Cocco
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Golf Club Toscana
- Casa Del Cioccolato Perugina
- Things to do Montalcino
- Nature and outdoors Montalcino
- Food and drink Montalcino
- Things to do Province of Siena
- Art and culture Province of Siena
- Food and drink Province of Siena
- Sports activities Province of Siena
- Nature and outdoors Province of Siena
- Tours Province of Siena
- Sightseeing Province of Siena
- Things to do Tuscany
- Art and culture Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Food and drink Tuscany
- Wellness Tuscany
- Sightseeing Tuscany
- Sports activities Tuscany
- Nature and outdoors Tuscany
- Things to do Italy
- Food and drink Italy
- Nature and outdoors Italy
- Art and culture Italy
- Sports activities Italy
- Wellness Italy
- Tours Italy
- Entertainment Italy
- Sightseeing Italy
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes