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Holiday rentals in Montalcino

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Montalcino

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

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Guest favourite
Home
4.96 out of 5 average rating, 130 reviews

Palazzo Monaci - Piscina nelle crete Senesi

Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

Top guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guest house
4.97 out of 5 average rating, 221 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Guest favourite
A spacious open-plan living area is displayed, featuring a modern kitchen with sleek cabinetry and an island. The dining table is set for meals, and a comfortable sofa is positioned in the background. Natural light fills the room, highlighting the wooden beams overhead.
Flat
4.89 out of 5 average rating, 115 reviews

La Casa di Bruna

LA CASA DI BRUNA Un appartamento finemente ristrutturato, arredato con amore e cura nei dettagli, si trova all’interno di un palazzo storico L’ingresso si apre su un salone con comodissimo divano collegato ad un'ampia e confortevole cucina Dalla sala accediamo alla terrazza con affaccio sulla fortezza dove si possono godere tramonti meravigliosi Sullo stesso piano troviamo un bagno e una luminosa camera matrimoniale Al piano superiore vi è il secondo bagno ed un'altra confortevole camera

Top guest favourite
A rustic stone farmhouse is nestled in a lush green landscape, surrounded by rolling hills and tall cypress trees. The sun casts a warm glow on the exterior, highlighting the charming architecture. An open courtyard with a small pool can be seen in the foreground.
Farm stay
4.92 out of 5 average rating, 586 reviews

Agriturismo Poggio Bicchieri ap. Memoria

Rilassati con tutta la famiglia in questo alloggio. L’agriturismo si compone di due appartamenti indipendenti con sala, cucina, camera e bagno. Non dovrai condividere nulla con il altri ospiti poiché é stata nostra cura organizzare tutto in maniera che ognuno abbia i propri spazi e tutto sia separato. All'esterno c’é un barbecue, tavolo con sedie e le sdraio. Nelle vicinanze Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino e Bagni San Filippo. Per raggiungerci 1,5 km di strada sterrata!

Top guest favourite
A medieval stone tower stands tall against a clear blue sky, showcasing its historic architecture. The narrow road lined with greenery leads to the entrance, with the texture of the stonework and windows highlighted, inviting guests to explore its unique charm.
Tower
5 out of 5 average rating, 108 reviews

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Top guest favourite
A spacious terrace is showcased with two comfortable armchairs positioned around a glass table. Potted red flowers adorn the railing, overlooking a panoramic view of the rolling hills of the Tuscan countryside under a partly cloudy sky.
Apartment
4.99 out of 5 average rating, 134 reviews

Suite "Note di Paesaggio"

The 80 sqm Suite "Note di paesaggio" is located on the second floor of a historic building where it meets the landscape of the Val d'Orcia. It is divided into several rooms including a furnished double bedroom with air conditioning overlooking the terrace, a living room with a panoramic view, a study with a desk, a marble bathroom with shower, and another double bedroom without air conditioning . You can enjoy a 30sqm terrace and its suggestive view of the countryside.

Top guest favourite
A serene outdoor area features well-maintained vineyards and gently sloping hills in the background. A shaded seating area is positioned beneath a large canopy, with rustic seating options visible. The landscape is complemented by a stone wall and lush greenery, creating a calm and inviting environment.
Farm stay
4.96 out of 5 average rating, 74 reviews

Cappella - agriturismo immerso nelle vigne

L’appartamento Cappella fa parte dell'agriturismo Le Chiuse, una struttura del 1840 immersa nelle vigne. E' ricavato da una piccola chiesetta sconsacrata, composto da un salotto con angolo cottura, poltrone e caminetto, un’ampia camera da letto matrimoniale, un bagno con box doccia, uno stanzino ed un soppalco con un letto matrimoniale. Dotato di aria condizionata. La finestra della camera da letto principale è dotata di zanzariera. Apertura piscina Giugno-Ottobre

Top guest favourite
A view from the window reveals a serene landscape of rolling hills and valleys bathed in soft morning light. The garden below is adorned with colorful flowers and greenery, enhancing the tranquil atmosphere of the Tuscan countryside.
Home
4.99 out of 5 average rating, 225 reviews

Alma Vignoni - Vignoni Val d'Orcia - Bagno Vignoni

Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

Top guest favourite
A rustic stone farmhouse is embraced by mature olive trees and lush greenery. The building features traditional window shutters and is set against a clear blue sky, with a gravel pathway leading up to the entrance, enhancing the tranquil countryside ambiance.
Farm stay
4.98 out of 5 average rating, 109 reviews

Podere Pereti Nuovi-modern Tuscan Villa

Podere I Pereti was entirely build by our grandfather Remo in the 1970's. My siblings and I spent most of our summers on the porch with our grandparents watching sunsets and admiring the view of the Val d'Orcia. Entirely surrounded by vineyards and olive groves. Nonno Remo, besides having a building company, proudly produced Orcia red wine that was consumed by the family. From the 150 olive trees, every November we filled our tanks with green gold olive oil.

Guest favourite
The bedroom features a spacious bed with light bedding. Natural light floods in through the windows, illuminating the wooden beams and antique furniture, including a tall wooden wardrobe and a small table with a chair. A mirror adds subtle charm to the room.
Home
4.96 out of 5 average rating, 153 reviews

Casa delle Giuggiole

Facing the old medieval walls of this ancient city, the location of the house will make you feel relaxed thanks to the peacefulness of the countryside and the vitality of the centre. Bathed in the gorgeous sunlight from sunrise to sunset, Casa delle Giuggiole will give you a sensation of lightness and freedom. Look through any one of the many windows and you can admire both the astonishing landscape of the Val d'Orcia and the typical Tuscan roofs.

Superhost
A spacious bedroom features a double bed dressed in white linens, with a cozy armchair in the corner. Natural light enters through a window, illuminating the stone wall beside wooden beams above. A wooden table displays snacks and additional seating is available.
Apartment
4.9 out of 5 average rating, 314 reviews

La Casetta di Brunello,very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

Guest favourite
An outdoor terrace features a glass dining table surrounded by four metal chairs, shaded by a large umbrella. Lush greenery and colorful flowers enhance the view, while decorative planters filled with plants add vibrancy to the space.
Home
4.98 out of 5 average rating, 157 reviews

Panoramic nest in Montalcino

A completely independent accommodation recently refurbished - from the design to the furnishings - directly by the host. It is composed of a living room with a fully equipped kitchen and a bedroom with bathroom. The peculiarity of the property is the extremely favorable location in the historic center, with a splendid terrace with panoramic garden on the Val d'Orcia, with barbecue, hammock, sink and outdoor shower.

Popular amenities for Montalcino holiday rentals

When is the best time to visit Montalcino?

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Avg. price£111£105£108£108£114£120£120£123£118£112£113£113
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Frequently Asked Questions

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

    Experience the best of Montalcino with our farmstay rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there house rentals with a dedicated workspace in Montalcino?

    Yes! Work meets play with ease at over 60 house rentals in Montalcino featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly condo rentals in Montalcino?

    Four-legged friends are welcome in Montalcino. Choose from more than 30 condo rentals for guests traveling with pets.

  • Are there Montalcino house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 50 house rentals with pools in Montalcino, available on Airbnb. Make a splash and soak up the sun in style!

  • Do farmstay rentals in Montalcino have air conditioning?

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

  • Do apartment rentals in Montalcino have a kitchen?

    Absolutely! We offer over 340 apartment rentals with a kitchen 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.

  • Do house rentals in Montalcino have free parking?

    Absolutely! We offer over 100 house rentals with free parking in Montalcino. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly condo rentals in Montalcino?

    Montalcino has more than 30 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Enhance your stay in our Villa Rentals with the most popular amenities: over 80 homes with a kitchen, over 70 homes with free parking, over 60 homes with air conditioning, over 80 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Montalcino

  • Total holiday rentals

    Explore 970 holiday rentals in Montalcino

  • Nightly prices starting at

    Montalcino holiday rentals start at £37 per night before taxes and fees

  • Verified guest reviews

    Over 28,460 verified reviews to help you choose

  • Family-friendly holiday rentals

    490 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 550 rentals that welcome pets

  • Holiday rentals with a pool

    400 properties feature pools

  • Rentals with dedicated workspaces

    400 properties have a dedicated workspace

  • Wifi availability

    910 of Montalcino holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Montalcino rentals

  • 4.8 Average rating

    Montalcino stays are highly rated by guests – averaging 4.8 out of 5!

Destinations to explore

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