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 condo rentals in Montalcino?

Experience the best of Montalcino with our condo rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Do house rentals in Montalcino have air conditioning?

Absolutely! We offer over 70 house rentals with air conditioning in Montalcino. Enjoy a tailored experience with all the comforts you desire.

Are there pet-friendly condo rentals in Montalcino?

Four-legged friends are welcome in Montalcino. Choose from more than 20 condo rentals for guests traveling with pets.

Do apartment rentals in Montalcino have a bbq area?

Absolutely! We offer over 90 apartment rentals with a bbq area 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 castle rentals in Montalcino have wifi?

Absolutely! We offer over 10 castle 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 condo rentals in Montalcino?

Montalcino has more than 20 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

What are the most popular amenities for Apartment Rentals in Montalcino?

Enhance your stay in our Apartment Rentals with the most popular amenities: over 90 homes with a bbq area, over 170 homes with air conditioning, over 320 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Montalcino vacation rentals

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.

0 of 0 items showing

1 of 3 pages

Superhost

Home in San Casciano in Val di pesa

4.83 out of 5 average rating, 88 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

Step under archways into a home where the original wood ceilings and tiled floors showcase Tuscan style. Enjoy delicious meals on the terrace with sweeping views of Tuscany, winters curled up in front of a huge fire place or relaxing on warm summer days by the pool. Savour the best of Tuscan food and wine with cooking classes with a Michelin chef, master classes in wine and visits to local artisan cheese and wine makers. Listed by Condé Nast as one of the most beautiful villas in Italy.

Guest favorite

Home in Prato

4.98 out of 5 average rating, 128 reviews

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment, there might still be availability. Turquoise: https://www.airbnb.com/rooms/plus/9430389

Superhost

Villa in Petrignano

4.98 out of 5 average rating, 51 reviews

Restored Farmhouse & Cottage with AC, Pool & WIFI

Villa La Quercia is a private 2 acre property consisting of a beautifully restored farmhouse and cottage- both exclusively for you during your stay. The property is surrounded by farmland and forest providing complete privacy and tranquility, yet the nearest village is only 3kms away. The property comfortably sleeps up to 12 people and has a large salt water filtered swimming pool. Fabulous restaurants, wineries and stunning Tuscan & Umbrian villages are but a short drive. Welcome.

Guest favorite

Villa in Figline Valdarno

4.98 out of 5 average rating, 44 reviews

Il Castellaccio di Figline

L'alloggio si trova al PRIMO PIANO di una villa immersa nel verde denominata “Il Castellaccio”, che deve il suo nome alla vicinanza con le rovine del vecchio castello appartenuto alla famiglia degli Uberti. La casa gode di una magnifica vista sulla campagna circostante ed è ideale per una vacanza rilassante per famiglie o gruppi di amici, con la possibilità di visitare città d’arte e godere degli splendidi paesaggi del Chianti, nonché delle specialità enogastronomiche della zona.

Guest favorite

Home in Bolsena

5 out of 5 average rating, 53 reviews

Bolsena House

This is our vacation home in beautiful Bolsena. We rent it out when we do not use it ourselves. This view is from our rooftop terrace. It overlooks the Santa Cristina Basilica and Bolsena lake - the largest lake of volcanic origin in Europe. Our house is located in the center of the old town, only a few minutes walk from the waterfont with its charming marina, peaceful beaches and numerous good restaurants. Pets are allowed upon request.

Guest favorite

Villa in Allerona

5 out of 5 average rating, 28 reviews

Vakantievilla Casale Colline Dolci

This luxurious villa (casale) is located near the village of Allerona on the border of Tuscany and Umbria and is 15 km from Orvieto, 100 km from Rome and 120 km from Florence. Casale Colline Dolci is perfect for guests who want to enjoy in all comfort and tranquility the beauty of the Italian countryside and its excellent cuisine, but equally ideal for those who want to soak up the beautiful culture of Italy.

Guest favorite

Apartment in Sasso D'ombrone

4.83 out of 5 average rating, 53 reviews

Holiday house "La Sartina"

Lovely newly renovated house (2023) with a beautiful view of the Ombrone Valley, where you can admire a wonderful sunrise and appreciate the wonderful Tuscan Maremma. Excellent finishes, 4 beds, air conditioning, very central to the typical Tuscan village Sasso D'Ombrone. 100 meters from the Bar/Market/Emporio, post office and bus stop. 1500m from Albus Alpacas (Alpaca Experience). Serious and helpful owner.

Superhost

Vacation home in Ortignano Raggiolo

5 out of 5 average rating, 14 reviews

Casa Paolina, typical property in Tuscany

Holiday home in Tuscan style, rustic and cozy, finely renovated respecting the tradition of the place. Equipped with every comfort, it will give joy and relaxation to young and old with its large garden, pool and hot tub. Our guests will be able to stay in complete privacy in our structure immersed in nature, in a small village of medieval origin, entirely pedestrian, forged by time and past generations.

Superhost

Apartment in Bucine

4.75 out of 5 average rating, 4 reviews

Lupinari Estate - La Limonaia

Tenuta Lupinari is located in the Valdambra, one of the most evocative and pristine places in the Chianti area. Our apartments are the result of a careful restoration of a 16th-century village immersed in the Tuscan hills, strategically located between Arezzo, Siena and Florence, an ideal place both to spend days relaxing and to visit the artistic beauties of our Land of Tuscany.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Montalcino vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Montalcino's top sights

Pienza555 locals recommend

Valdorcia6 locals recommend

Monte Oliveto Maggiore Abbey126 locals recommend

Abbey of Sant'Antimo104 locals recommend

Murlo25 locals recommend

Centro Benessere Le Terme6 locals recommend

Other great vacation rentals in Montalcino

Superhost

Home in Poppi

4.8 out of 5 average rating, 5 reviews

Villa for 22 people w/private pool

Guest favorite

Apartment in Mercatale Valdarno

4.98 out of 5 average rating, 80 reviews

Panoramic view from stone Apartment- Pool and A/C

Guest favorite

Villa in Lucignano

4.96 out of 5 average rating, 23 reviews

Villa Serena

Guest favorite

Farm stay in Camucia

5 out of 5 average rating, 7 reviews

Il Giardino degli Ulivi | Casa Ippocastano

Superhost

Apartment in Croce

4.85 out of 5 average rating, 40 reviews

And Tre Lecci

Guest favorite

Apartment in Città della Pieve

5 out of 5 average rating, 31 reviews

the cloudy

Superhost

Apartment in Arezzo

4.5 out of 5 average rating, 4 reviews

Pozzale Apartment 2+2 | 50m

Superhost

Home in Monteroni D'arbia

4.88 out of 5 average rating, 185 reviews

La Torre di Corsanello

Show all

Quick stats about vacation rentals in Montalcino

Total rentals
960 properties
Total number of reviews
24K reviews
Family-friendly rentals
530 properties are a good fit for families
Pet-friendly rentals
540 properties allow pets
Rentals with a pool
390 properties have a pool
Rentals with dedicated workspaces
350 properties have a dedicated workspace

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 condo rentals in Montalcino?
Experience the best of Montalcino with our condo rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Montalcino have air conditioning?
Absolutely! We offer over 70 house rentals with air conditioning in Montalcino. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly condo rentals in Montalcino?
Four-legged friends are welcome in Montalcino. Choose from more than 20 condo rentals for guests traveling with pets.
Do apartment rentals in Montalcino have a bbq area?
Absolutely! We offer over 90 apartment rentals with a bbq area 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 castle rentals in Montalcino have wifi?
Absolutely! We offer over 10 castle 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 condo rentals in Montalcino?
Montalcino has more than 20 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Apartment Rentals in Montalcino?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 90 homes with a bbq area, over 170 homes with air conditioning, over 320 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Montalcino vacation rentals

Top-rated vacation rentals in Montalcino

Home in San Casciano in Val di pesa

Home in Prato

Villa in Petrignano

Villa in Figline Valdarno

Home in Bolsena

Villa in Allerona

Apartment in Sasso D'ombrone

Vacation home in Ortignano Raggiolo

Apartment in Bucine

Farm stay in Greve in Chianti

Farm stay in Roccatederighi

Apartment in Siena

Vacation rentals for every style

Apartments

Houses

Villas

Popular amenities for Montalcino vacation rentals

Stay near Montalcino's top sights

Other great vacation rentals in Montalcino

Home in Poppi

Apartment in Mercatale Valdarno

Villa in Lucignano

Farm stay in Camucia

Apartment in Croce

Apartment in Città della Pieve

Apartment in Arezzo

Home in Monteroni D'arbia

Quick stats about vacation rentals in Montalcino

Total rentals

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with a pool

Rentals with dedicated workspaces

Frequently Asked Questions

Destinations to explore