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Asciano Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Asciano holiday rentals

Breakfast, lunch, dinner served; local cuisine
Hotel San Gregorio

Residence in Pienza

Hotel San Gregorio
3.0 star property
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is HK$1,591
HK$1,804 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio
Lobby lounge
ApartHotel Anghel

Apartment in Siena

ApartHotel Anghel
8.4 out of 10, Very good, (334)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is HK$547
HK$638 total
includes taxes & fees
16 Dec - 17 Dec
ApartHotel Anghel
View from room
Abbadia Sicille Relais

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is HK$560
HK$644 total
includes taxes & fees
14 Dec - 15 Dec
Abbadia Sicille Relais
View from room
Tuscasì Aparthotel

Aparthotel in Sovicille

Tuscasì Aparthotel
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is HK$546
HK$627 total
includes taxes & fees
12 Dec - 13 Dec
Tuscasì Aparthotel
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Residence in Siena City Centre

Il Battistero Siena - Residenza d'Epoca
9.6 out of 10, Exceptional, (191)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Pool
Farmhouse in the hills with panoramic view and swimming pool

Holiday Home in Ristonchia

Farmhouse in the hills with panoramic view and swimming pool
9.6 out of 10, Exceptional, (75)
"Was wonderful and beautiful. "
United States
Alana A.
Farmhouse in the hills with panoramic view and swimming pool
Exterior
Farmhouse in the heart of the real chiantishire

Holiday Home in Castellina in Chianti

Farmhouse in the heart of the real chiantishire
10.0 out of 10, Exceptional, (148)
"We loved our stay! The Farmhouse is really lovely and the view out the back is exceptional. We enjoyed a lot of home cooked meals with the most stunning view. Daniele was amazing to communicate with as well. Definitely hope to be back one day! "
Australia
Rebekah T.
Farmhouse in the heart of the real chiantishire
Private kitchen
Regis Condo

Apartment in Siena City Centre

Regis Condo
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo
Pool
Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Villa in Siena

Private and cozy retreat in Montalcino with private pool surrounded by vineyards
9.4 out of 10, Exceptional, (67)
"What a lovely place, I will recommend this fabulous home to friends and family and will be returning sometime soon."
United Kingdom
peter H.
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Front of property – evening/night
Casanova - Panoramic Rooms and Suites

Residence in San Quirico d'Orcia

Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
The price is HK$1,525
HK$1,714 total
includes taxes & fees
12 Dec - 13 Dec
Casanova - Panoramic Rooms and Suites
Exterior
Il Poggio dell'Eremita

Villa in Sinalunga

Il Poggio dell'Eremita
10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
The price is HK$1,100
HK$1,281 total
includes taxes & fees
12 Dec - 13 Dec
Il Poggio dell'Eremita
View from room
Residenza d'Epoca Palazzo Borghesi

Residence in Siena City Centre

Residenza d'Epoca Palazzo Borghesi
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
The price is HK$1,475
HK$1,659 total
includes taxes & fees
6 Jan - 7 Jan 2026
Residenza d'Epoca Palazzo Borghesi
Banquet hall
agriturismo la roggiola

Cottage in Monticiano

agriturismo la roggiola
9.6 out of 10, Exceptional, (112)
"A Nice Home in nature with a lot of animals."
Germany
Tabea S.
agriturismo la roggiola
Free WiFi, bed sheets
Bellarmino Boutique Apartments

Apartment in Montepulciano

Bellarmino Boutique Apartments
6.0 out of 10, (1)
"Heat didnt work, it was FREEZING. Contact didnt seem to be local, seemed like they were managing remotely and couldnt or wouldnt send anyone to help. Nor did they really seem to care. Beautiful area though!"
United States
JON
The price is HK$774
HK$888 total
includes taxes & fees
11 Jan - 12 Jan 2026
Bellarmino Boutique Apartments
Exterior detail
The House of Alice, charm and relaxation

Holiday Home in Montalcino (SI)

The House of Alice, charm and relaxation
9.8 out of 10, Exceptional, (66)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
The price is HK$1,357
HK$1,837 total
includes taxes & fees
11 Jan - 12 Jan 2026
The House of Alice, charm and relaxation
Lobby
Residenza Fabroni

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is HK$740
HK$851 total
includes taxes & fees
15 Dec - 16 Dec
Residenza Fabroni
Exterior
Camping Siena Colleverde

Camping in Scacciapensieri

Camping Siena Colleverde
3.0 star property
8.2 out of 10, Very good, (159)
"Safe, great proximity to Siena without being too close, nice pool."
United States
Martha
Camping Siena Colleverde
Outdoor dining
Villa with large garden in the Chianti hills

Holiday Home in Siena

Villa with large garden in the Chianti hills
9.6 out of 10, Exceptional, (75)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
United States
Jessica P.
Villa with large garden in the Chianti hills
Property grounds
"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool

Villa in Belforte

"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool
10.0 out of 10, Exceptional, (78)
"What an awesome place. Lovely house and backyard with pool. Leo is friendly , helpful and welcoming . Belforte is a small , quiet hilltop village but it is very accessible (by car) to other awesome spots- Siena, San Gimignano , Volterra and others. Highly recommended "
New Zealand
Adrian d.
"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool
Exterior
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Villa in Castellina in Chianti

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
10.0 out of 10, Exceptional, (64)
"Gorgeous property - we had a wonderful stay "
United Kingdom
Michelle D.
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Asciano Hotel Reviews

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent
"Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!"
Pedro 1-night trip
Posted 5 days ago
Relais Villa Grazianella - UNA Esperienze

Find out more about Asciano

Search for holiday rentals in Asciano on Expedia! You can easily find your home rentals, villas, holiday apartments in Asciano using one of the methods below:

  • View our selection of featured holiday rentals in Asciano
  • Use the map to find apartments and other holiday homes in the Asciano neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Asciano while they last

Look no further and take a look at our great range of rental properties in Asciano!

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Frequently asked questions

Can I find a holiday rental in Asciano?

Yes, there are holiday rentals close to the most popular sights in Asciano, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the countryside in Asciano. Make sure you have time to check out the wineries and coffee shops during your trip.

What are some of the best holiday rentals that Asciano has to offer?

Farmhouse in the heart of the real chiantishire: This holiday home rental outside of Asciano is located in a rural location, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Asciano?

Expedia has 23 holiday rentals for your stay in Asciano.

What can I see and do in Asciano?

While exploring the area, visit family-friendly sights like Siena Circuit, or get outside and enjoy nature at Val di Chiana. Other places in town to visit include Monte Oliveto Maggiore Abbey and Museo Cassioli.

What are holiday rentals like in Asciano?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Asciano. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for small groups.