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Vacation rentals in Asciano

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Asciano

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

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Top guest favourite
Condo in Buonconvento
5 out of 5 average rating, 39 reviews

Romantic cottage in Tuscany with pool and garden

A romantic residence immersed in the greenery of the Tuscan countryside, ideal for a couple who want to take a break from everyday life and regenerate in total tranquility. An intimate and quiet place, designed for those seeking relaxation, nature and absolute privacy. The apartment gives the unique feeling of being the owners of an eighteenth-century Tuscan farmhouse, surrounded by hills and authentic landscapes. The swimming pool is at your complete disposal and is perfect for moments of absolute relaxation, between sun and quiet

Top guest favourite
Home in Asciano
5 out of 5 average rating, 11 reviews

[NEW] Epic Poolside Break with a View of Siena

A stone's throw from Siena, in the most authentic heart of Tuscany, between Chianti, Val d'Orcia, Montalcino and Montepulciano. The house is set in one of the most photographed and iconic landscapes in the region, among rolling hills, cypress trees, white roads and sunsets that give unforgettable emotions. Ideal for families, couples, and for cycling and hiking enthusiasts! Book, and you will receive a link with all our recommended experiences, including food and wine, tours, bike rentals, and much more.

Guest favourite
Home in Asciano
5 out of 5 average rating, 5 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 in Asciano
4.96 out of 5 average rating, 119 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
An aerial view captures the agriturismo surrounded by lush green fields and a neatly arranged row of tall cypress trees. The inviting pool reflects the serene landscape, and the winding dirt road leads towards the property, nestled amid the picturesque Crete Senesi.
Apartment in Asciano
4.97 out of 5 average rating, 162 reviews

Loggia 1 in farmhouse with shared pool

Apartment for 2 people in the Santa Lucia farmhouse (farmhouse DIVIDED IN 7 APARTMENTS) in the Crete Senesi, 10 km from Siena. Located on the second floor with a private table in front of the windows of the entrance loggia. It consists of a double bedroom (two single beds joined to form a double bed), a bathroom with shower and a living room with functional kitchen. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room FOR A FEE according to consumption.

Guest favourite
Home in Asciano
4.97 out of 5 average rating, 34 reviews

Casa Olivo | Il Fossaccio Farm

Casa Olivo is one of 8 charming residences that make up the Podere il Fossaccio. Nestled in the heart of the romantic Crete Senesi, the entire farmhouse is built from local stone and exudes timeless charm. Casa Olivo features a cozy private area in front of the house—perfect for candlelit dinners or watching Tuscan sunsets—Wi-Fi, a beautiful shared swimming pool, and on-site parking, allowing you to experience the dream of a romantic getaway surrounded by nature and tradition. CIR 052002LTN0097

Guest favourite
Farm stay in Castelnuovo Berardenga
4.92 out of 5 average rating, 315 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
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, 210 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.

Superhost
Apartment in Asciano
4.71 out of 5 average rating, 7 reviews

"Il Glicine" apartment with pool

Apartment for families with children, couples and for business travelers, it is located on the first floor, it is composed of a bathroom with shower, kitchen, living room and bedroom with double bed with panoramic view. wifi in all rooms is free. Outside available to customers there are areas with gazebos where you can eat outside and use the barbecue. Extra services on request: heating 15 euros per day and air conditioning 15 euros per day. Pets welcome pay 25 euros per stay per pet on site

Top guest favourite
Aerial view of a charming countryside villa surrounded by rolling hills and vineyards. Olive trees are visible lining the roads, which lead to the home nestled within a serene natural landscape. The colors and textures reflect the characteristic beauty of the Tuscan countryside.
Condo in Asciano
4.98 out of 5 average rating, 298 reviews

Celeste – The color of the summer sky in Tuscany

The apartment is located on the 2nd floor and consists of 2 bedrooms (possibility of making single or double beds on request), a bathroom, a living room, and a kitchen equipped for cooking. (Washing machine available from 9 a.m. to 8 p.m. in the laundry room) Free parking and wifi. Convenient location for visiting Tuscany's tourist centers. We are in the countryside, in the heart of the Crete Senesi, a car is recommended to be independent and visit the magnificent Tuscan countryside

Guest favourite
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 in Asciano
4.96 out of 5 average rating, 67 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
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
4.92 out of 5 average rating, 249 reviews

Casa al Gianni - Hut

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Popular amenities for Asciano vacation rentals

When is the best time to visit Asciano?

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Avg. price$151 CAD$172 CAD$177 CAD$201 CAD$204 CAD$212 CAD$238 CAD$233 CAD$215 CAD$201 CAD$202 CAD$227 CAD
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 vacation rentals in Asciano

  • Total vacation rentals

    Explore 760 vacation rentals in Asciano

  • Nightly prices starting at

    Asciano vacation rentals start at $42 CAD per night before taxes and fees

  • Verified guest reviews

    Over 15,520 verified reviews to help you choose

  • Family-friendly vacation rentals

    430 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 380 rentals that welcome pets

  • Vacation rentals with a pool

    500 properties feature pools

  • Rentals with dedicated workspaces

    230 properties have a dedicated workspace

  • Wifi availability

    680 of Asciano vacation 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