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Asciano Vacation Rentals

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Check prices for these dates

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

Our top choices for Asciano vacation rentals

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

Hotel San Gregorio

3.0 star property
Pienza
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
$132 nightly
The price is $152
Dec 11 - Dec 12
Total with taxes and fees
Hotel San Gregorio
Lobby lounge
ApartHotel Anghel

ApartHotel Anghel

Siena
8.4 out of 10, Very Good, (334)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
$62 nightly
The price is $72
Dec 10 - Dec 11
Total with taxes and fees
ApartHotel Anghel
View from room
Abbadia Sicille Relais

Abbadia Sicille Relais

4.0 star property
Trequanda
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
$76 nightly
The price is $88
Dec 10 - Dec 11
Total with taxes and fees
Abbadia Sicille Relais
Royal Apartment | View from room
Tuscasì Aparthotel

Tuscasì Aparthotel

Sovicille
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
$74 nightly
The price is $85
Dec 21 - Dec 22
Total with taxes and fees
Tuscasì Aparthotel
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Siena City Centre
9.6 out of 10, Exceptional, (191)
"Great location and friendly staff. "
United States
Parissa
$152 nightly
The price is $172
Dec 20 - Dec 21
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca
Pool
Farmhouse in the hills with panoramic view and swimming pool

Farmhouse in the hills with panoramic view and swimming pool

Ristonchia
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

Farmhouse in the heart of the real chiantishire

Castellina in Chianti
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
Grand Apartment with Garden | Private kitchen | Full-size fridge, microwave, oven, stovetop
Regis Condo

Regis Condo

Siena City Centre
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
$86 nightly
The price is $99
Dec 10 - Dec 11
Total with taxes and fees
Regis Condo
Pool
Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Siena
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

Casanova - Panoramic Rooms and Suites

3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
Casanova - Panoramic Rooms and Suites
Exterior
Il Poggio dell'Eremita

Il Poggio dell'Eremita

Sinalunga
10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
$162 nightly
The price is $165
Dec 10 - Dec 11
Total with taxes and fees
Il Poggio dell'Eremita
Panoramic Suite, City View | View from room
Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi

Siena City Centre
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
$185 nightly
The price is $209
Jan 9 - Jan 10, 2026
Total with taxes and fees
Residenza d'Epoca Palazzo Borghesi
Banquet hall
agriturismo la roggiola

agriturismo la roggiola

Monticiano
9.6 out of 10, Exceptional, (112)
"A Nice Home in nature with a lot of animals."
Germany
Tabea S.
agriturismo la roggiola
Deluxe Apartment, 2 Bedrooms, Balcony | Free WiFi, bed sheets
Bellarmino Boutique Apartments

Bellarmino Boutique Apartments

Montepulciano
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
$106 nightly
The price is $122
Dec 11 - Dec 12
Total with taxes and fees
Bellarmino Boutique Apartments
Exterior detail
The House of Alice, charm and relaxation

The House of Alice, charm and relaxation

Montalcino (SI)
9.8 out of 10, Exceptional, (66)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
$247 nightly
The price is $251
Dec 10 - Dec 11
Total with taxes and fees
The House of Alice, charm and relaxation
Lobby
Residenza Fabroni

Residenza Fabroni

Montepulciano
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
$77 nightly
The price is $90
Dec 15 - Dec 16
Total with taxes and fees
Residenza Fabroni
Exterior
Camping Siena Colleverde

Camping Siena Colleverde

3.0 star property
Scacciapensieri
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

Villa with large garden in the Chianti hills

Siena
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

"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool

Belforte
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

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Castellina in Chianti
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

Hotel Athena

Hotel Athena

10/10 Excellent
"Excellent hotel, very helpful staff, highly recommended "
Vikram 3-night trip
Posted 3 days ago
Hotel Athena

Find out more about Asciano

Everything you need to know about Asciano vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Asciano vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Asciano vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Asciano vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Asciano. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Asciano in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $72 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Asciano rentals

At Expedia, we put the best Asciano vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Asciano rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Asciano vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Asciano. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Asciano?

Yes, we give you a choice of vacation rentals close to popular local attractions in Asciano, or you can choose 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 coffeehouses during your trip.

What's the top vacation rental that Asciano has to offer?

Borgo Argiano: You might like this vacation home rental near Asciano. It is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a coffee maker. You can relax into your vacation with a garden and a library.

How many vacation rentals are there in Asciano?

Expedia has 21 vacation 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 vacation rentals like in Asciano?

Vacation rentals are private properties you can reserve for several days or more in Asciano. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family gatherings.