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Holiday houses in Monticiano

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Monticiano

  • Total holiday rentals

    Explore 70 holiday rentals in Monticiano

  • Nightly prices starting at

    Monticiano holiday rentals start at $84 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,190 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Monticiano holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Monticiano rentals

  • 4.8 Average rating

    Monticiano stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated holiday rentals in Monticiano

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

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Top Guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.93 out of 5 average rating, 285 reviews

Casa al Gianni - Hut

Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!

LocationFamilyAccess

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 in Campiglia D'orcia
4.92 out of 5 average rating, 620 reviews

Poggio Bicchieri Holiday Farm - Memoria apartment

Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

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Top Guest favourite
Apartment in Asciano
4.9 out of 5 average rating, 20 reviews

Incredible Views & Pool in the Tuscan Hills

Fuggite nel cuore della Toscana e vivete un soggiorno immersi in dolci colline, una bellezza senza tempo e panorami indimenticabili. La casa offre l'accesso a una splendida piscina in comune e a tranquilli spazi esterni, perfetti per rilassarsi al sole o godersi serate serene. All'interno, troverete comfort, stile, tutto il necessario per un soggiorno memorabile. Ideale per coppie, famiglie o gruppi di amici che desiderano vivere un'autentica esperienza toscana a breve distanza in auto da Siena.

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Top Guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 154 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

LocationFamilyQuiet

Top Guest favourite
Cottage in Monticiano
5 out of 5 average rating, 39 reviews

Typical Tuscan Cottage with swimming pool and park

Il Country Cottage è ubicato nel cuore della Toscana autentica, in un territorio incontaminato, con una biodiversità unica. Sito a soli 5 minuti di auto dalla famosa Abbazia di San Galgano e da l'Eremo di Montesiepi, dove è custodita la prestigiosa "Spada nella Roccia". Viene affittata l'intera proprietà: la tipica casa toscana di campagna, la piscina, il giardino e il parco recintato. Una location perfetta per rilassarsi con la massima privacy, senza lo stress ed il logorio della vita moderna

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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.
Guesthouse in Macciano
4.97 out of 5 average rating, 240 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.

LocationFamilyComfort

Guest favourite
An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.
Holiday home in Sovicille
4.97 out of 5 average rating, 160 reviews

Podere La Castellina - No. 1 COTTAGE

Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

ValueLocationAccess

Top Guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.92 out of 5 average rating, 327 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

ValueLocationOutdoor spaces

Guest favourite
Condo in Monticiano
4.98 out of 5 average rating, 62 reviews

Il TramontO

The TramontO is a completely renovated elegant and rustic apartment surrounded by the nature of Tuscany, with panoramic views, garden, terrace and mini-whirlpool for exclusive USE. Many details in natural wood and antique stone stand out. A few steps from the Abbey of San Galgano, which can also be reached by an enchanting path 5 km from the village. 35 km from Siena and 92 km from Florence, built from a historic tower from the 1200s, it offers charm, relaxation and unforgettable sunsets.

ValueLocationAir conditioning

Guest favourite
Dome in Volterra
4.96 out of 5 average rating, 156 reviews

Green Dome @ The Land Before Time Retreats

Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

LocationFamilyAir conditioning

Top Guest favourite
The outdoor pool area features a light blue water surface complemented by three tiered fountains. A small white table with a glass is placed on the wooden deck, surrounded by two white chairs. The rustic stone buildings create a charming backdrop, adorned with greenery.
Apartment in Montalcino
4.99 out of 5 average rating, 117 reviews

Castel Brunello - 2 doublebed rooms + terrace

Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.

ValueFamilyComfort

Top Guest favourite
A charming rural building features large windows and stone walls, surrounded by lush greenery. The entrance includes a few steps leading to a door framed by vibrant flower pots, while a well-maintained lawn extends in front.
Farm stay in Monticiano
5 out of 5 average rating, 36 reviews

Romantic and quiet stay near Siena, with garden

The apartment is great for 2 people. In the apartment there are a kitchen, a large double bedroom and a bathroom. In the bedroom you can add a bed for baby. FREE WIFI - Mbps download 25,45 e Mbps in upload 3,03 THE PRICE INCLUDES ALL CONSUMPTION AND TOURIST TAX The car is necessary, parking is free and next to the house.

LocationFamilyView

Popular amenities for Monticiano holiday rentals

When is the best time to visit Monticiano?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$197 NZD$199 NZD$194 NZD$195 NZD$177 NZD$298 NZD$177 NZD$168 NZD$177 NZD$162 NZD$175 NZD$197 NZD
Avg. temp8°C8°C11°C13°C18°C22°C25°C25°C21°C17°C12°C9°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Monticiano?

    Monticiano has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Monticiano?

    Experience the best of Monticiano with our apartment 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.

  • Are there pet-friendly vacation rentals in Monticiano?

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

  • Are there vacation rentals with a dedicated workspace in Monticiano?

    Yes! Work meets play with ease at over 20 vacation rentals in Monticiano featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Monticiano villa rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 villa rentals with pools in Monticiano, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in Monticiano have a kitchen?

    Absolutely! We offer over 20 apartment rentals with a kitchen in Monticiano. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Monticiano have wifi?

    Absolutely! We offer over 10 villa rentals with wifi in Monticiano. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Monticiano have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in Monticiano. Enjoy a tailored experience with all the comforts you desire.