
Vacation rentals in Montalcino
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Top-rated vacation rentals in Montalcino
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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.

Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

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.

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

Montalcino Townhouse with Private Garden & Spa
A luxury apartment that blends traditional elements with all the modern comforts and some contemporary wall art. The apartment is centrally located in the upper part of town, only around the corner from the main square, in the limited traffic area. You can drive close by to download the luggage. The closest free car park is located at less than 10 minutes walk. Please note that to reach the house you need to walk a fairly steep street: it may not be ideal for those with mobility problems.

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.

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.

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.

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.

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.

Casa al Gianni - Capanna
Ciao, siamo Cristina & Carmelo! Vi invitiamo a vivere un’esperienza autentica nel nostro agriturismo “Casa al Gianni” situato 20 min da Siena. Il nostro marchio è la vita semplice a stretto contatto con la natura e gli animali della nostra fattoria. Immerso tra i boschi e la splendida campagna toscana trascorrerai una vacanza indimenticabile. Questo angolo di paradiso ti rimarrà nel cuore!

Agriturismo Poggio Bicchieri ap. Poesia
Il nostro agriturismo è una finestra sulla val d'orcia, composto da 2 appartamenti con cucina, camera e bagno. Grande giardino attrezzato. Immerso nel silenzio, vicino a Pienza, Montalcino, Bagno Vignoni e le terme naturali di Bagno San Filippo. Per raggiungerci è molto semplice, l'ultimo km di strada è sterrata ma percorribile da tutti.
Popular amenities for Montalcino vacation rentals
Stay near Montalcino's top sights
Other great vacation rentals in Montalcino

S.Ilaria - Private pool Villa with 2 bedrooms

Casa Tòrta - comfort room

gazebo con vetrate scorrevoli

Tuscan villa in the heart of the Val d'Orcia

Dimora del Vino

Cipressini 2 - piscina e vista mozzafiato

Podere Belsogno

Panoramic view & outdoor jacuzzi - Pienza
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ455 | ﺩ.ﺇ463 | ﺩ.ﺇ510 | ﺩ.ﺇ536 | ﺩ.ﺇ566 | ﺩ.ﺇ591 | ﺩ.ﺇ595 | ﺩ.ﺇ606 | ﺩ.ﺇ584 | ﺩ.ﺇ551 | ﺩ.ﺇ477 | ﺩ.ﺇ481 |
| Avg. temp | 8°C | 8°C | 11°C | 13°C | 18°C | 22°C | 25°C | 25°C | 21°C | 17°C | 12°C | 9°C |
Frequently Asked Questions
Are there farmstay rentals with a dedicated workspace in Montalcino?
Yes! Work meets play with ease at over 60 farmstay rentals in Montalcino featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in villa rentals in Montalcino?
Experience the best of Montalcino with our villa 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.
Do castle rentals in Montalcino have air conditioning?
Absolutely! We offer over 10 castle rentals with air conditioning in Montalcino. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly apartment rentals in Montalcino?
Four-legged friends are welcome in Montalcino. Choose from more than 200 apartment rentals for guests traveling with pets.
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 apartment rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 140 apartment rentals with pools in Montalcino, available on Airbnb. Make a splash and soak up the sun in style!
Do bed and breakfast rentals in Montalcino have a kitchen?
Absolutely! We offer over 20 bed and breakfast rentals with a kitchen in Montalcino. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Montalcino have free parking?
Absolutely! We offer over 250 apartment 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 Apartment Rentals in Montalcino?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 250 homes with free parking, over 200 homes with air conditioning, over 330 homes with a kitchen, over 340 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Montalcino

Total vacation rentals
Explore 990 vacation rentals in Montalcino

Nightly prices starting at
Montalcino vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

Verified guest reviews
Over 27,280 verified reviews to help you choose

Family-friendly vacation rentals
530 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 560 rentals that welcome pets

Vacation rentals with a pool
430 properties feature pools

Rentals with dedicated workspaces
390 properties have a dedicated workspace

Wi-Fi availability
940 of Montalcino vacation rentals include wi-fi 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
- Rentals with a hot tub Montalcino
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- Lake Trasimeno
- Lake Bolsena
- Feniglia
- Cala Violina
- Gulf of Baratti
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Tenuta Le Velette
- Cala di Forno
- Castiglion del Bosco Winery
- Golf Club Toscana
- Riva del Marchese
- Spiaggia di Marina di Grosseto
- Santa Maria della Scala
- Cavallino Matto
- Pubblico Palace
- CavallinoMatto
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Podere La Marronaia, Sosta alle Colonne
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Podere Il Cocco
- Madonna del Latte
- Things to do Montalcino
- Food and drink Montalcino
- Things to do Siena
- Sightseeing Siena
- Art and culture Siena
- Food and drink Siena
- Sports activities Siena
- Tours Siena
- Nature and outdoors Siena
- Things to do Tuscany
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