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Holiday rentals in Asciano

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Asciano

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

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Top guest favourite
An aerial view reveals a charming country house nestled among rolling hills. Olive trees and vineyards extend across the landscape, while a winding road leads to the property, which is framed by tall cypress trees and lush greenery.
Apartment
4.99 out of 5 average rating, 222 reviews

Pink like the sunset sky

The apartment is located on the 2nd floor, consisting of 2 bedrooms (possibility of making double or single beds depending on the needs of the customer), a bathroom, large living room and kitchen equipped for cooking. TV, (for those who request it, a washing machine is available from 9 a.m. to 8 p.m. in our laundry room). To come to us, a car is recommended, to be independent, and to visit the Tuscan countryside. Convenient location for visiting Tuscany I look forward to showing you the real Tuscany!

Guest favourite
Home
5 out of 5 average rating, 7 reviews

"Le Arcate" apartment in an 18th-century farmhouse

Relax with the whole family in this quiet accommodation, the rooms are separated by stone and brick arches. We are secluded but not isolated: we are located 800 meters from the center of the village of Asciano (Si), 25 km from Siena, which can also be reached by train. The Terme di Rapolano are 7 km away, while the Val d'Orcia is 40 km away. In an hour it is possible to reach Florence: Pienza, Montalcino, Bagni Vignone, San Quirico d 'orcia, etc. 10 minutes away is the Abbey of Monte Oliveto Maggiore.

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

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Guest favourite
Farm stay
4.92 out of 5 average rating, 336 reviews

Apartment in Tuscan farm house.

Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.

Top guest favourite
An aerial view captures the agriturismo surrounded by lush green fields and rows of tall cypress trees. A shared swimming pool is visible within the landscaped garden, offering a serene spot for relaxation amidst the natural beauty of the Crete Senesi.
Flat
4.95 out of 5 average rating, 99 reviews

Siena - apartment in the countryside near Siena

The Siena apartment for 5 people is located in the Santa Lucia farmhouse (DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is an apartment of about 100 square meters, located on the ground floor, consisting of three bedrooms (one double; one with two beds and one single), a large living room with fireplace, kitchen, two bathrooms with shower. Private outdoor gazebo with table and benches located in a private garden. AIR CONDITIONING in the rooms for a FEE according to consumption.

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.

Top guest favourite
Home
5 out of 5 average rating, 18 reviews

Sosta Eroica • Panoramic View & Quiet Pool Retreat

A pochi minuti da Siena, nel cuore autentico della Toscana, un luogo di pace relax e silenzio . vivi un soggiorno da sogno tra le Crete Senesi , Chianti, Val d’Orcia, Montalcino e Montepulciano. La casa è immersa in un paesaggio iconico di colline, cipressi e tramonti mozzafiato. Perfetta per coppie, famiglie e amanti della natura. Prenota e scopri esperienze uniche: degustazioni, tour e attività per vivere la Toscana come un local e a fine giornata rilassati nella nostra stupenda piscina .

Superhost
The image depicts a tranquil swimming pool with sparkling turquoise water, reflecting the surrounding greenery and a distant stone building. Tall cypress trees line the area, enhancing the serene landscape, while sun loungers are arranged neatly near the pool's edge.
Home
4.91 out of 5 average rating, 74 reviews

Family Forest - Pool in the Crete Senesi

Relax with the whole family in our hideaway in Palazzo Monaci in the heart of the Crete Senesi! Our apartment is located in a residence with a swimming pool and breathtaking views, ideal for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favourite
The landscape features rolling green hills under a clear sky, with a rustic building nestled among the greenery. A gravel road winds through the scene, leading towards the structure, which is surrounded by trees and distant hills.
Apartment
5 out of 5 average rating, 20 reviews

Casa Biancospino Crete Senesi | Podere Fossaccio

Casa Biancospino is an apartment with a private courtyard inside the Podere Fossaccio. Suitable for short and medium/long stays and is located in the heart of the Crete Senesi. The location is strategic for visiting the most interesting places in Tuscany. The green areas and a magnificent infinity pool overlooking the surrounding hills will be available to you and the other guests of the Podere. A warm and welcoming atmosphere where you can breathe the authentic Tuscan atmosphere.

Top guest favourite
A spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.
Apartment
5 out of 5 average rating, 46 reviews

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Top guest favourite
A yurt is shown at night, illuminated warmly from within. The starry sky features the Milky Way, providing a stunning backdrop. An outdoor seating area with a thatched roof is visible, showcasing a tranquil atmosphere amidst a natural landscape.
Yurt
4.98 out of 5 average rating, 193 reviews

2 ❤️ and 1 Yurt Glamping in Tuscany for adults only

Romantic glamping for adults, in the heart of the Tuscan countryside. Silver Yurt, 35 m² + private en-suite bathroom, 7 m² + private outdoor wood-fired hot tub* (*EXTRA CHARGE), private relaxation veranda. Heated in winter and air-conditioned in summer. Dinners with delivery directly to the Yurt, available for an even tastier experience (*SURCHARGE*). - Private parking, WiFi - Kitchen with refrigerator, microwave, (NO STOVE) + private outdoor barbecue.

Top guest favourite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Apartment
5 out of 5 average rating, 145 reviews

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Popular amenities for Asciano holiday rentals

When is the best time to visit Asciano?

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Avg. price£109£110£107£108£110£114£128£125£116£108£109£122
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°C

Frequently Asked Questions

  • What are the best places to stay in Asciano?

    Asciano has welcoming stays in countryside villas, stone farmhouses, and central town apartments. Many accommodations let you experience the area’s rural charm and scenic surroundings, while some are near historic piazzas or offer views of rolling hills.

  • What are the best things to do in Asciano with kids?

    Explore local parks, discover interactive exhibits at small museums, or join family-friendly cooking classes. Many visitors enjoy walking in the Tuscan countryside and visiting olive groves around Asciano.

  • What are some of the best things to do in Asciano?

    Explore the Abbey of Monte Oliveto Maggiore, stroll Asciano’s medieval streets, and visit museums highlighting Etruscan and local art. Enjoy tasting traditional Tuscan dishes at village trattorias, and wander among the scenic cypress-lined landscapes.

  • How is the weather in Asciano?

    Asciano has mild winters, with January temperatures around 33–49°F (0–9°C), and warm summers peaking at 89°F (31°C) in July and August. Expect wetter months in spring and autumn, with drier, sun-filled days in summer.

  • When is the best time to visit Asciano?

    Late spring and early autumn are often recommended for comfortable temperatures and vibrant landscapes. Many visitors appreciate the fields turning green or golden, and some festivals take place as the seasons change.

  • What are the best places to visit in Asciano?

    Frequently suggested sites include the Abbey of Monte Oliveto Maggiore, the Museo Civico Archeologico e d'Arte Sacra, and the Church of Sant’Agata. The historic town center is known for its quiet streets and local markets.

  • What are some hiking trails in Asciano?

    Asciano has trails that wind through the Crete Senesi hills and among cypress groves, with routes suitable for various fitness levels. Many visitors enjoy exploring paths near Monte Oliveto Maggiore and the surrounding countryside.

  • What are some family activities we can do in Asciano?

    Visit small museums with interactive displays, explore farm visits where children can see animals, and walk through the historic town center together. Some families enjoy taking part in workshops showcasing traditional crafts or foods.

  • What are some of the best day trip ideas from Asciano?

    Consider exploring nearby villages known for their medieval streets, visiting thermal baths, or discovering historic abbeys and Tuscan wineries. Siena and Val d'Orcia are frequently suggested for a blend of art, history, and countryside beauty.

  • Are there any pet friendly accommodations available in Asciano?

    Many accommodations in the Asciano area welcome guests with pets, especially in countryside farmhouses or rentals with outdoor spaces. Walking trails and open fields around town make it easy to explore with your companion animal.

  • What are some local tips for visiting Asciano?

    Try local olive oil and pecorino cheese at village markets, and carry a light layer for cooler evenings, especially in spring and autumn. Walking shoes are useful for exploring both historic streets and countryside trails.

  • What is Asciano known for?

    Asciano is known for its medieval heritage, striking Crete Senesi landscapes, and traditional Tuscan cuisine. Historic abbeys, art-filled churches, and the area’s winding cypress-lined roads are often highlighted by visitors.

  • What are the best hidden gems to explore in Asciano?

    The small Church of San Francesco with its frescoes, artisan workshops in quiet backstreets, and lesser-known walking paths through the hills are often suggested as hidden gems. Local cafés offer a glimpse of daily life in Asciano.

  • What are the best foods to try in Asciano?

    Frequent favorites include handmade pici pasta, pecorino cheese, and dishes prepared with local saffron. Regional sweets such as ricciarelli and cantucci are often enjoyed with a glass of Vin Santo dessert wine.

  • What should I bring for a trip to Asciano?

    Pack comfortable walking shoes, layered clothing for fluctuating spring or autumn temperatures, and a sun hat for the summer months. A camera is helpful for capturing the unique landscapes and local architecture.

  • What is the nightlife in Asciano like?

    Asciano’s nightlife is typically low-key, with wine bars, village cafés, and occasional live music. Many visitors enjoy relaxed evenings trying regional wines or joining local community events in the main square.

  • What are the most popular events or festivals in Asciano?

    Asciano has recurring celebrations, including harvest festivals, traditional food fairs, and cultural events often held in the main piazza during spring and autumn. Some festivals highlight local music, crafts, or agricultural traditions.

  • Are there family friendly vacation rentals in Asciano?

    Asciano has a variety of family-friendly vacation rentals, including spacious countryside homes and central apartments with kitchen facilities. Outdoor spaces and child-friendly amenities are frequently found in these accommodations.

Quick stats about holiday rentals in Asciano

  • Total holiday rentals

    Explore 760 holiday rentals in Asciano

  • Nightly prices starting at

    Asciano holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 15,740 verified reviews to help you choose

  • Family-friendly holiday rentals

    450 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 390 rentals that welcome pets

  • Holiday rentals with a pool

    500 properties feature pools

  • Rentals with dedicated workspaces

    240 properties have a dedicated workspace

  • Wifi availability

    670 of Asciano holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Asciano rentals

  • 4.8 Average rating

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

Destinations to explore

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