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Vacation rentals in Asciano

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Top-rated vacation rentals in Asciano

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

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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
4.91 out of 5 average rating, 515 reviews

Poggio Bicchieri Holiday Farm - Memoria apartment

Relax with all the families in this home. 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 arranged 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!

Guest favorite
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home in Asciano
4.96 out of 5 average rating, 102 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 favorite
Farm stay in Castelnuovo Berardenga
4.92 out of 5 average rating, 309 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 favorite
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, 141 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.

Top guest favorite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Apartment in Montepulciano
4.97 out of 5 average rating, 119 reviews

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

Top guest favorite
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, 200 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 favorite
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, 291 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 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 Strategic location for visiting the tourist centers of Tuscany. 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 favorite
A heated mini hydro-massage pool is surrounded by greenery, featuring subtle chromotherapy lighting in shades of purple. In the background, a rustic farmhouse is set against a serene twilight sky, with tall cypress trees lining the space.
Villa in Monteroni d'Arbia
4.98 out of 5 average rating, 107 reviews

San Giovanni in Poggio, villa Meriggio 95mq

Detached house, two double bedrooms, two bathrooms with shower, living room with fully equipped kitchen (dishwasher, washing machine, oven, microwave), double sofa bed, private garden with equipped pergola. Satellite TV and free Wi-Fi. Additional services at the property, upon reservation, include Focus brand Jarifa2 6.7 pedal-assisted bicycles and a wellness area with a Forest outdoor Finnish sauna and a heated mini-pool with hydromassage and chromotherapy with panoramic views.

Top guest favorite
An exterior view of a charming Tuscan house featuring warm stone walls. The surrounding garden includes manicured grass and potted plants. A spacious patio with a table for outdoor dining is visible, alongside a stone pathway leading to the entrance.
Guesthouse in Montefollonico
4.97 out of 5 average rating, 113 reviews

Casale Santa Barbara - Exclusive Apartment

At a glance: • Location: perfect entry door to the Val d’Orcia between Pienza (8,5 km) and Montepulciano (8,5 km). • Charming warm old stones Tuscan house – completely restored in 2016 • Big apartment (100m2), designed for 2 persons, completely independent, fully furnished, Tuscan style with modern equipment. • Exclusivity: we are living on the 1st floor; the ground floor is yours. You are our only guests. • Spacious private garden (+ 300m2) • Stunning view on the Tuscan hills.

Top guest favorite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci
5 out of 5 average rating, 101 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Top guest favorite
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 in San Quirico d'Orcia
4.99 out of 5 average rating, 219 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 favorite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 431 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Popular amenities for Asciano vacation rentals

When is the best time to visit Asciano?

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Avg. priceG$22,794 GYDG$25,931 GYDG$26,767 GYDG$30,322 GYDG$30,740 GYDG$31,995 GYDG$35,968 GYDG$35,132 GYDG$32,413 GYDG$29,486 GYDG$26,558 GYDG$25,094 GYD
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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Asciano?

    Four-legged friends are welcome in Asciano. Choose from more than 400 vacation rentals for guests traveling with pets.

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

    Yes! Work meets play with ease at over 240 vacation rentals in Asciano featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Asciano vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 560 vacation homes with pools in Asciano, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly vacation rentals in Asciano?

    Asciano has more than 470 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do castle rentals in Asciano have free parking?

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

  • Do house rentals in Asciano have wifi?

    Absolutely! We offer over 80 house rentals with wifi in Asciano. Enjoy a tailored experience with all the comforts you desire.

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

    Experience the best of Asciano with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do condo rentals in Asciano have a kitchen?

    Absolutely! We offer over 60 condo rentals with a kitchen in Asciano. Enjoy a tailored experience with all the comforts you desire.

  • Do serviced apartment rentals in Asciano have air conditioning?

    Absolutely! We offer over 10 serviced apartment rentals with air conditioning in Asciano. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Farmstay Rentals in Asciano?

    Enhance your stay in our Farmstay Rentals with the most popular amenities: over 90 homes with a kitchen, over 40 homes with air conditioning, over 70 homes with free parking, over 100 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Asciano

  • Total vacation rentals

    Explore 820 vacation rentals in Asciano

  • Verified guest reviews

    Over 15,170 verified reviews to help you choose

  • Family-friendly vacation rentals

    470 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 400 rentals that welcome pets

  • Vacation rentals with a pool

    560 properties feature pools

  • Rentals with dedicated workspaces

    240 properties have a dedicated workspace

  • Wi-Fi availability

    740 of Asciano vacation rentals include wi-fi 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