Holiday rentals near Monte Oliveto Maggiore Abbey

We found 3,123 holiday rentals — enter your dates for availability

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October 2025

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Take a look at holiday rentals close to Monte Oliveto Maggiore Abbey that provide the perfect home base for your trip. Whether you're going on holiday with family or friends, holiday homes have the amenities that you expect for your stay, which might include cable TV and a washer and dryer. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Monte Oliveto Maggiore Abbey

Showing deals for:2 Jan - 9 Jan

Exceptional

(11 reviews)

"Borgo dei Fondi" Splendid Farmhouse free wifi-free parking

Siena, Tuscany

5% off

for 7 nights, 1 villa

AU$1,019 per night

includes taxes & fees

Winery Luxury Villa immersed in the area of the Nobile di Montepulciano docg.

Exceptional

(14 reviews)

Winery Villa in the heart of Nobile Vineyards.

Montepulciano, Toscana

9% off

for 7 nights, 1 villa

AU$1,089 per night

includes taxes & fees

Exceptional

(104 reviews)

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

Siena, Toscana

14% off

for 7 nights, 1 villa

AU$927 per night

includes taxes & fees

Exceptional

(43 reviews)

Borgo dei Fondi – Tuscan Oasis with Pool, Just Minutes from Siena

Siena, Tuscany

6% off

for 7 nights, 1 home

AU$384 per night

includes taxes & fees

Exceptional

(21 reviews)

FARMH. PODERE CUNINA 25 KM SUD SIENA / MONTALCINO PRENDENDO LEZIONI DI CUCINA

Buonconvento

8% off

for 7 nights, 1 room

AU$396 per night

includes taxes & fees

Exceptional

(25 reviews)

Wonderful new villa in Maremma, near Montalcino and Castiglione della Pescaia

Montalcino, Toscana

9% off

for 7 nights, 1 villa

AU$964 per night

includes taxes & fees

Exceptional

(24 reviews)

LA LOGGIA. HOUSE WITH STUNNING VIEW ABOVE THE CHIANTI REGION AND PANORAMIC POOL

Castelnuovo Berardenga, Tuscany

8% off

for 7 nights, 1 apartment

AU$392 per night

includes taxes & fees

Exceptional

(44 reviews)

Villa with private pool, air conditioning near wineries at 3km from village

Chianciano Terme, Tuscany

9% off

for 7 nights, 1 villa

AU$1,242 per night

includes taxes & fees

Exceptional

(19 reviews)

Camparone, ArcenoRentalsClub Magnificent Chianti Villa Exclusive Pool Concierge

Castelnuovo Berardenga, Provincia di Siena

14% off

for 7 nights, 1 villa

AU$2,905 per night

includes taxes & fees

Exceptional

(13 reviews)

Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.

San Giovanni d'Asso, Provincia di Siena

9% off

for 7 nights, 1 villa

AU$3,389 per night

includes taxes & fees

Exceptional

(8 reviews)

Apartment in renovated farmhouse in typical Chianti Tuscan village

Castelnuovo Berardenga, Toscana

7% off

for 7 nights, 1 home

AU$250 per night

includes taxes & fees

Exceptional

(65 reviews)

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

Montalcino, Tuscany

9% off

for 7 nights, 1 villa

AU$409 per night

includes taxes & fees

Exceptional

(20 reviews)

FABULOUS 6BR HOME WITH WONDERFUL SWIMMING POOL & GARDEN IN THE HEART OF TUSCANY!

Lucignano, Tuscany

9% off

for 7 nights, 1 villa

AU$1,000 per night

includes taxes & fees

Exceptional

(24 reviews)

Villa Banditello, secluded, panoramic view over Montepulciano valley.

Torrita di Siena, Tuscany

9% off

for 7 nights, 1 home

AU$527 per night

includes taxes & fees

Exceptional

(34 reviews)

Beautiful house on garden with shared pool just a few minutes Siena Tuscany

Siena, Tuscany

9% off

for 7 nights, 1 home

AU$1,151 per night

includes taxes & fees

Exceptional

(9 reviews)

Casa di Sotto, Podere Ampella: a beautiful holiday house in the heart of Tuscany

Montalcino, Siena

9% off

for 7 nights, 1 home

AU$502 per night

includes taxes & fees

Exceptional

(5 reviews)

LA RONDINAIA. CHARMING HOUSE WITH GARDEN AND POOL. AMAZING VIEW

Castelnuovo Berardenga, Provincia di Siena

8% off

for 7 nights, 1 apartment

AU$392 per night

includes taxes & fees

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Find the best place to stay - Monte Oliveto Maggiore Abbey

Premier Host

Il Casale Di Manuele 12, Emma Villas

Sleeps 12 · 6 bedrooms · 7 bathrooms

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

Sleeps 6 · 2 bedrooms · 2 bathrooms

Top rated rentals - Monte Oliveto Maggiore Abbey

Premier Host

Beautiful stay

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

Premier Host

Private villa with private pool close to Montisi.

We loved our stay at Luigi's villa and have the best memories of our time there. The villa was very clean including the pool. Once we had a small problem with the washing machine and Luigi was so fast in sorting it out for us. He also provided us with lots of information about Montisi (a delightful hill top village, a bit off the beaten track) and the surrounding area. The photos was a good reflection of the villa, the pool and garden. We would love to go back one day. Annemarie Veldsman. Date of stay: June 2024.

Anne H.

Stayed June 2024

Premier Host

Great place

A great apartment in a lovely Tuscan village. Host was extremely helpful and available at all times. Would recommend.

Sharon B.

Stayed Apr 2024

Premier Host

Fabulous in every way

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

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