Holiday Homes near Walls of Monteriggioni, Castellina in Chianti: House Rentals & More

Find the perfect holiday home within close proximity to Walls of Monteriggioni. Holiday rentals offer the amenities that you expect for your family, friends or furry companion, such as a fireplace and garden. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.

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Find the best place to stay - Walls of Monteriggioni

Showing deals for: 27 Oct - 30 Oct

Ancient farm situated in the heart of the Chianti Classico Senese, Pool and View

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 home

AU$289 per night

includes taxes & fees

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

Sleeps 2 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

AU$247 per night

includes taxes & fees

Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.

Sleeps 4 · 2 bedrooms · 1+ bathroom

for 3 nights, 1 home

AU$313 per night

includes taxes & fees

CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

Sleeps 4 · 2 bedrooms · 1 bathroom

for 3 nights, 1 room

AU$348 per night

includes taxes & fees

"La Casina delle Fate" a pretty little house in Tuscany

Sleeps 2 · 2 bedrooms

for 3 nights, 1 home

AU$160 per night

includes taxes & fees

Villa with large garden in the Chianti hills

Sleeps 5 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$198 per night

includes taxes & fees

Top rated rentals - Walls of Monteriggioni

Premier Host

Amazing

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!

Rebekah T.

Stayed July 2025

Premier Host

A slice of Tuscan heaven

My family, including my parents and children, spent the most wonderful week at this beautiful property! The house and private outdoor terrace is huge, with lots of different spaces to spend eating and drinking and relaxing. The pool was incredible - the kids loved the diving board and making friends with other children who were also staying in the hamlet. It was the perfect house for us to spend a week relaxing in Tuscany!

Amanda O.

Stayed Aug 2019

Premier Host

Amazing

Our stay was incredible! Everything as per pictures, Sergio and Elena were very helpful!! Would definitely recommend this place ! You can’t get a better view or place than this!!

Jenelle C.

Stayed Apr 2019

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value