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Montalcino vacation rentals

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Top-rated vacation rentals in Montalcino

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Villa in Murlo

5 out of 5 average rating, 11 reviews

Pompana Rustic Charm Casale

Scopri con Wp Relais l'incanto di Pompana, un antico borgo etrusco immerso nelle colline toscane, dove abbiamo trasformato un vecchio rudere in pietra in una splendida casa rurale indipendente su due piani. Al piano terra, un'accogliente area living open space offre un angolo salotto con camino, una cucina con tavolo da pranzo e un grazioso bagno di servizio. Dal piano terra, accedi a un intimo terrazzo coperto da tettoia con vista panoramica, ideale per pranzi e cene immerse nella natura.

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

Condo in Montepulciano

4.93 out of 5 average rating, 209 reviews

HOLIDAY APARTMENT IN HISTORICAL PALACE- MARINA

The apartment is located in an historical palace in the very heart of the old town. Near to all monuments, shops and restaurants but extremely quiet and peaceful. The old town is a pedestrian area . The flat is at the second floor. There is a lift for luggage and wheelchairs. From the windows you can enjoy a wonderful view. The apartment has recently been refurbished to a very high standard and furnished with elegance and traditional Tuscan antiques.

Guest favorite

Villa in Allerona

5 out of 5 average rating, 29 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

4.82 out of 5 average rating, 55 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.

Guest favorite

Apartment in San Gimignano

4.93 out of 5 average rating, 103 reviews

Apartment "Il Nespolo" - Sunflower Location

The apartment "Il Nespolo", location "Girasole", is located in the historic center of San Gimignano, just 150 meters from Piazza del Duomo, in a cross street of the main street. The property is located in the immediate vicinity of all points of interest and at the same time away from the noise of the busiest street in the country.

Guest favorite

Villa in Loro Ciuffenna

4.91 out of 5 average rating, 23 reviews

Villa with pool & view near Florence and Arezzo

Tuscan 1700 farmhouse in dominant position with a stunning view over the Valdarno valley. Features six separate apartments with 1 or 2 bedrooms each (total 7 bedrooms plus added beds), private gardens, private swimming pool (open May - September), common lounge and kitchen, WI-FI in every apartment. For groups up to 20 persons.

Superhost

Farm stay in Pienza

4.8 out of 5 average rating, 165 reviews

Holidays in Piandimaggio in Val d 'Orcia.

Holidays in Piandimaggio The farmhouse "Piandimaggio" Tuscan farmhouse from the early 1900s with 4 new apartments The farmhouse is located in the heart of the Val d'Orcia natural park near Pienza and Bagno Vignoni and with a splendid view of Mount Amiata.

Guest favorite

Farm stay in Greve in Chianti

4.87 out of 5 average rating, 188 reviews

La Capanna delle Bartaline

L'appartamento si trova all'interno della nostra azienda agricola ad 1 Km. da Panzano. E' di nuova ristrutturazione e ben curato nei dettagli, confortevole e luminoso, adatto per ogni tipo di soggiorno. Vista mozzafiato sulle colline toscane.

Superhost

Apartment in Scrofiano

5 out of 5 average rating, 4 reviews

Apartment with patio, A/C

Newly renovated apartment for 4 people. With private patio, garden, located in medieval village. Every bedroom has air condition. Beautiful, quiet place, few steps from forest an d waterfalls.

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

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

Farm stay in Camucia

5 out of 5 average rating, 7 reviews

Il Giardino degli Ulivi | Casa Ippocastano

Superhost

Villa in Radicondoli

4.94 out of 5 average rating, 17 reviews

A Romantic Villa in the heart of Tuscany

Guest favorite

Villa in Asciano

4.95 out of 5 average rating, 75 reviews

Podere on the Crete Senesi

Superhost

Villa in Terranuova Bracciolini

5 out of 5 average rating, 3 reviews

Casa al Fiume - Villa with exclusive pool

Guest favorite

Home in Certaldo (Fi)

4.87 out of 5 average rating, 60 reviews

Paluffo Torre House

Superhost

Cottage in san gimignano

4.78 out of 5 average rating, 32 reviews

Glicine romantic cottage in country

Superhost

Apartment in Arezzo

4.5 out of 5 average rating, 4 reviews

Pozzale Apartment 2+2 | 50m

Show all

Quick stats about vacation rentals in Montalcino

  • Total rentals

    950 properties

  • Total number of reviews

    24K reviews

  • Family-friendly rentals

    520 properties are a good fit for families

  • Pet-friendly rentals

    550 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 condo rentals with a dedicated workspace in Montalcino?

    Yes! Work meets play with ease at over 30 condo 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 condo rentals in Montalcino have air conditioning?

    Absolutely! We offer over 20 condo 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 farms in Montalcino have a bbq area?

    Absolutely! We offer over 110 farms 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 condo rentals in Montalcino have wifi?

    Absolutely! We offer over 50 condo rentals with wifi in Montalcino. Enjoy a tailored experience with all the comforts you desire.

  • Are there Montalcino vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 390 vacation homes with pools in Montalcino, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly farmstay rentals in Montalcino?

    Montalcino has more than 50 family-friendly farmstay rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Farmstay Rentals in Montalcino?

    Enhance your stay in our Farmstay Rentals with the most popular amenities: over 50 homes with air conditioning, over 120 homes with wifi, 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