Asciano Monte Oliveto Maggiore Station holiday rentals
We found 3,412 holiday rentals — enter your dates for availability
Scroll through and discover holiday rentals near Asciano Monte Oliveto Maggiore Station that provide the perfect home base for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the best amenities for spending time at your holiday home, which might include parking and a pool. At the end of the day, you'll find a property to rent for everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Asciano Monte Oliveto Maggiore Station
Showing deals for:17 Oct - 24 Oct
Image gallery for Charming Villa with swimming pool in the heart of Tuscany
1010 out of 10 rating
Exceptional
(25 reviews)
Charming Villa with swimming pool in the heart of Tuscany
Cortona
5% off
Price is AU$15,248
AU$15,248
AU$2,178 per night
includes taxes & fees
Image gallery for Chiusarella Arceno Rentals Club Chianti Villa exclusive Pool Concierge freeWiFi
1010 out of 10 rating
Exceptional
(32 reviews)
Chiusarella Arceno Rentals Club Chianti Villa exclusive Pool Concierge freeWiFi
Castelnuovo Berardenga, Tuscany
14% off
Price is AU$14,426
AU$14,426
AU$2,061 per night
includes taxes & fees
Image gallery for Villino Cortona - Holiday home with private pool, wifi, a/c - Tuscany
1010 out of 10 rating
Exceptional
(22 reviews)
Villino Cortona - Holiday home with private pool, wifi, a/c - Tuscany
Cortona, AR
23% off
Price is AU$1,663
AU$1,663
AU$238 per night
includes taxes & fees
Image gallery for Camparone, ArcenoRentalsClub Magnificent Chianti Villa Exclusive Pool Concierge
1010 out of 10 rating
Exceptional
(19 reviews)
Camparone, ArcenoRentalsClub Magnificent Chianti Villa Exclusive Pool Concierge
Castelnuovo Berardenga, Provincia di Siena
14% off
Price is AU$19,510
AU$19,510
AU$2,787 per night
includes taxes & fees
Image gallery for Special offer Newly renovated fine detached villa with fireplace.
8.68.6 out of 10 rating
Excellent
(11 reviews)
Special offer Newly renovated fine detached villa with fireplace.
Castelnuovo Berardenga, Tuscany
9% off
Price is AU$1,329
AU$1,329
AU$190 per night
includes taxes & fees
Image gallery for "Borgo dei Fondi" Il Forno Ground Floor free wifi-free parking
1010 out of 10 rating
Exceptional
(20 reviews)
"Borgo dei Fondi" Il Forno Ground Floor free wifi-free parking
Siena, Tuscany
6% off
Price is AU$2,150
AU$2,150
AU$307 per night
includes taxes & fees
Image gallery for FABULOUS 6BR HOME WITH WONDERFUL SWIMMING POOL & GARDEN IN THE HEART OF TUSCANY!
1010 out of 10 rating
Exceptional
(19 reviews)
FABULOUS 6BR HOME WITH WONDERFUL SWIMMING POOL & GARDEN IN THE HEART OF TUSCANY!
Lucignano, Tuscany
9% off
Price is AU$9,582
AU$9,582
AU$1,369 per night
includes taxes & fees
Image gallery for Mulino della Solaia, Arceno Rentals Club, Luxury Villa in Tuscany, pool, wifi
1010 out of 10 rating
Exceptional
(14 reviews)
Mulino della Solaia, Arceno Rentals Club, Luxury Villa in Tuscany, pool, wifi
Monticiano, Toscana
14% off
Price is AU$16,262
AU$16,262
AU$2,323 per night
includes taxes & fees
Image gallery for Agriturismo Il Salarco: Apartment
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Agriturismo Il Salarco: Apartment
Montepulciano, Tuscany
9% off
Price is AU$1,844
AU$1,844
AU$263 per night
includes taxes & fees
Image gallery for Idyllic guest house in Tuscan country house style with swimming pool
1010 out of 10 rating
Exceptional
(22 reviews)
Idyllic guest house in Tuscan country house style with swimming pool
Sinalunga, Siena
9% off
Price is AU$2,067
AU$2,067
AU$295 per night
includes taxes & fees
Image gallery for Traditional Tuscan farmhouse with breathtaking views 19 Minutes from Montalcino
1010 out of 10 rating
Exceptional
(18 reviews)
Traditional Tuscan farmhouse with breathtaking views 19 Minutes from Montalcino
Montalcino
9% off
Price is AU$2,387
AU$2,387
AU$341 per night
includes taxes & fees
Image gallery for Luxury Villa in Monticchiello, your heaven in Tuscany
1010 out of 10 rating
Exceptional
(52 reviews)
Luxury Villa in Monticchiello, your heaven in Tuscany
Pienza, Toscana
17% off
Price is AU$1,493
AU$1,493
AU$213 per night
includes taxes & fees
Image gallery for BEAUTIFUL VILLA with private Pool in the heart of Chianti
1010 out of 10 rating
Exceptional
(24 reviews)
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Castelnuovo Berardenga
5% off
Price is AU$12,876
AU$12,876
AU$1,839 per night
includes taxes & fees
Image gallery for Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property
8.48.4 out of 10 rating
Very good
(10 reviews)
Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property
Gaiole in Chianti, Toscana
8% off
Price is AU$1,737
AU$1,737
AU$248 per night
includes taxes & fees
Image gallery for Casa di Sotto, Podere Ampella: a beautiful holiday house in the heart of Tuscany
1010 out of 10 rating
Exceptional
(8 reviews)
Casa di Sotto, Podere Ampella: a beautiful holiday house in the heart of Tuscany
Montalcino, Siena
9% off
Price is AU$3,853
AU$3,853
AU$550 per night
includes taxes & fees
Image gallery for Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment
9.29.2 out of 10 rating
Wonderful
(25 reviews)
Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment
Civitella in Val di Chiana, Province of Arezzo
8% off
Price is AU$3,721
AU$3,721
AU$532 per night
includes taxes & fees
Image gallery for Lake House, Farm in the hills between Arezzo Florence Siena, Garden, Pool
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Lake House, Farm in the hills between Arezzo Florence Siena, Garden, Pool
Pergine Valdarno, Tuscany
13% off
Price is AU$1,297
AU$1,297
AU$185 per night
includes taxes & fees
Image gallery for Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena
1010 out of 10 rating
Exceptional
(16 reviews)
Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena
Montepulciano
9% off
Price is AU$6,756
AU$6,756
AU$965 per night
includes taxes & fees
Image gallery for Arco al Poggio, Arceno Rentals Club, Spacious Chianti Apt, Pool, Concierge, WiFi
1010 out of 10 rating
Exceptional
(63 reviews)
Arco al Poggio, Arceno Rentals Club, Spacious Chianti Apt, Pool, Concierge, WiFi
Castelnuovo Berardenga, Toscana
14% off
Price is AU$3,767
AU$3,767
AU$538 per night
includes taxes & fees
Image gallery for Casa Rossella - ArcenoRentalsClub Romantic flat in Chianti Wifi Concierge Pool
1010 out of 10 rating
Exceptional
(51 reviews)
Casa Rossella - ArcenoRentalsClub Romantic flat in Chianti Wifi Concierge Pool
Castelnuovo Berardenga, Province of Siena
14% off
Price is AU$2,669
AU$2,669
AU$381 per night
includes taxes & fees
Image gallery for Exclusive Stone Tower.
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Exclusive Stone Tower.
Casciano di Murlo, Tuscany
8% off
Price is AU$1,122
AU$1,122
AU$160 per night
includes taxes & fees
Image gallery for Casa Girolamo - Super Central with Private Parking
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Casa Girolamo - Super Central with Private Parking
Montepulciano, Provincia di Siena
9% off
Price is AU$1,854
AU$1,854
AU$265 per night
includes taxes & fees
Image gallery for Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
1010 out of 10 rating
Exceptional
(14 reviews)
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Siena, Toscana
14% off
Price is AU$3,478
AU$3,478
AU$497 per night
includes taxes & fees
Image gallery for Apartment in Farmhouse
1010 out of 10 rating
Exceptional
(6 reviews)
Apartment in Farmhouse
Montepulciano, Tuscany
8% off
Price is AU$1,261
AU$1,261
AU$180 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Asciano Monte Oliveto Maggiore Station
Showing deals for: 15 Oct - 18 Oct
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
Sleeps 10 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
76 reviews(76 reviews)
The current price is AU$1,325
AU$1,325
for 3 nights, 1 home
AU$442 per night
includes taxes & fees
LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center
Sleeps 2 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
The current price is AU$571
AU$571
for 3 nights, 1 apartment
AU$190 per night
includes taxes & fees
Panoramic villa surrounded by vineyards and olive groves, 6 km from Montepulciano. Ideal for familie
Sleeps 9 · 5 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
The current price is AU$1,363
AU$1,363
for 3 nights, 1 villa
AU$454 per night
includes taxes & fees
Magnificent ancient Castle
Sleeps 65 · 15 bedrooms · 9+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The current price is AU$12,077
AU$12,077
for 3 nights, 1 room
AU$4,026 per night
includes taxes & fees
CASTELLO NELLE CRETE
Sleeps 50 · 20 bedrooms · 22 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The current price is AU$73,228
AU$73,228
for 3 nights, 1 room
AU$24,409 per night
includes taxes & fees
House in Val d'Orcia excellent families CIN IT052024C2APXZK7PD
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
The current price is AU$626
AU$626
for 3 nights, 1 home
AU$209 per night
includes taxes & fees
Top rated rentals - Asciano Monte Oliveto Maggiore Station
Monticchiello
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
A wonderful quiet apartment with everything you need . Comfortable bed, good a/c, good shower, well equipped kitchen, lovely host. All uphill from the car park but that’s what you expect in a hilltop village. Excellent restaurants in the village. Not far from Pienza . And a washing machine and dryer!
Linda M.
Stayed Apr 2025
A pleasant stay near beautiful town of Montepulciano.
1010 out of 10
Exceptionalexceptional
38 reviews(38 reviews)
Thank you, Franco for your friendliness and for helping us with transport.
Anna H.
Stayed Dec 2024
Beautiful stay
1010 out of 10
Exceptionalexceptional
52 reviews(52 reviews)
We received a warm welcome from the family and a thorough explanation of the facilities, the surrounding area and places of interest. Fabrizio communicated easily with us using the translation phone app. The apartment is very clean, well equipped and offers a genuine Italian experience. Simply wonderful.
Murray H.
Stayed Oct 2024
Great place
1010 out of 10
Exceptionalexceptional
52 reviews(52 reviews)
A great apartment in a lovely Tuscan village. Host was extremely helpful and available at all times. Would recommend.
Sharon B.
Stayed Apr 2024
Rustic Charm
1010 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
The property was homely, rustic and welcoming.
The owners did everything to make us comfortable with their own produce and wine.
Liz and Martyn R.
Stayed July 2023
Fabulous in every way
1010 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
Just divine location, magnificent view...friendly hosts and lovely Tuscan house. We loved our stay with our 8 month old baby!
Stephanie B.
Stayed May 2019
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value