Holiday rentals near Il Cassero
We found 3,966 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals within easy reach of Il Cassero that provide the perfect home base for your trip. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you expect for your stay, which might include parking and a fireplace. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Il Cassero
Showing deals for:19 Sept - 26 Sept
Image gallery for ancient tuscany House with character with garden and swimming pool
9.89.8 out of 10 rating
Exceptional
(28 reviews)
ancient tuscany House with character with garden and swimming pool
Capolona, Tuscany
8% off
Price is AU$13,806
AU$13,806
AU$1,972 per night
includes taxes & fees
Image gallery for Stunning private Castle 9 BR - 8 BA with pool just 7 miles from Florence!
1010 out of 10 rating
Exceptional
(6 reviews)
Stunning private Castle 9 BR - 8 BA with pool just 7 miles from Florence!
Impruneta, Toscana
9% off
Price is AU$39,608
AU$39,608
AU$5,658 per night
includes taxes & fees
Image gallery for Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl
1010 out of 10 rating
Exceptional
(39 reviews)
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl
Greve in Chianti, Toscana
8% off
Price is AU$14,342
AU$14,342
AU$2,049 per night
includes taxes & fees
Image gallery for CHIANTI VILLA & studio, max12, super-large pool, hilltop secluded fab views,
9.89.8 out of 10 rating
Exceptional
(19 reviews)
CHIANTI VILLA & studio, max12, super-large pool, hilltop secluded fab views,
Gaiole in Chianti, Tuscany
9% off
Price is AU$7,176
AU$7,176
AU$1,025 per night
includes taxes & fees
Image gallery for Lovely country house in the Chianti region, for 4 persons, near Siena
9.09.0 out of 10 rating
Wonderful
(10 reviews)
Lovely country house in the Chianti region, for 4 persons, near Siena
Castellina in Chianti, Tuscany
13% off
Price is AU$1,982
AU$1,982
AU$283 per night
includes taxes & fees
Image gallery for Sangiovese Country House, apartment with pool in a small village in the hills of Chianti
1010 out of 10 rating
Exceptional
(17 reviews)
Sangiovese Country House, apartment with pool in a small village in the hills of Chianti
Tavarnelle Val di Pesa, Tuscany
6% off
Price is AU$2,357
AU$2,357
AU$337 per night
includes taxes & fees
Image gallery for Farmhouse 15th century in Chianti with private garden and lake
1010 out of 10 rating
Exceptional
(13 reviews)
Farmhouse 15th century in Chianti with private garden and lake
Radda in Chianti, Tuscany
8% off
Price is AU$2,092
AU$2,092
AU$299 per night
includes taxes & fees
Image gallery for A Panoramic Tuscan Luxury - Villa Maria in Fronzano
1010 out of 10 rating
Exceptional
(71 reviews)
A Panoramic Tuscan Luxury - Villa Maria in Fronzano
Reggello, Toscana
5% off
Price is AU$15,031
AU$15,031
AU$2,147 per night
includes taxes & fees
Image gallery for BEAUTIFUL VILLA with private Pool in the heart of Chianti
1010 out of 10 rating
Exceptional
(21 reviews)
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Castelnuovo Berardenga
5% off
Price is AU$14,993
AU$14,993
AU$2,142 per night
includes taxes & fees
Image gallery for Ancient house in Chianti Hills with private lake and garden
1010 out of 10 rating
Exceptional
(5 reviews)
Ancient house in Chianti Hills with private lake and garden
Radda in Chianti, Tuscany
8% off
Price is AU$1,950
AU$1,950
AU$279 per night
includes taxes & fees
Image gallery for Casale Chiesina. Villa in Tuscany for the EXCLUSIVE USE of the guest.
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Casale Chiesina. Villa in Tuscany for the EXCLUSIVE USE of the guest.
Bibbiena, Provincia di Arezzo
9% off
Price is AU$8,554
AU$8,554
AU$1,222 per night
includes taxes & fees
Image gallery for Typical Tuscan Residence near the farm la Vialla
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Typical Tuscan Residence near the farm la Vialla
Capolona, Toscana
8% off
Price is AU$1,217
AU$1,217
AU$174 per night
includes taxes & fees
Image gallery for Ancient Cottage in Chianti
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Ancient Cottage in Chianti
Castellina in Chianti, Tuscany
9% off
Price is AU$1,566
AU$1,566
AU$224 per night
includes taxes & fees
Image gallery for Stone Farmhouse in Chianti Hill between Florence, Siena private veranda and lake
1010 out of 10 rating
Exceptional
(33 reviews)
Stone Farmhouse in Chianti Hill between Florence, Siena private veranda and lake
Radda in Chianti, Tuscany
8% off
Price is AU$2,401
AU$2,401
AU$343 per night
includes taxes & fees
Image gallery for AGRITURISMO in FLORENTINE HILLS-CHIANTI. 100% Travelers Recommend.
1010 out of 10 rating
Exceptional
(11 reviews)
AGRITURISMO in FLORENTINE HILLS-CHIANTI. 100% Travelers Recommend.
Rignano sull'Arno, Tuscany
9% off
Price is AU$3,917
AU$3,917
AU$560 per night
includes taxes & fees
Image gallery for Ancient stone farmhouse on a top of Chianti Hill with private garden and lake
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Ancient stone farmhouse on a top of Chianti Hill with private garden and lake
Radda in Chianti, Tuscany
8% off
Price is AU$1,846
AU$1,846
AU$264 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$1,767
AU$1,767
AU$252 per night
includes taxes & fees
Image gallery for Charming House Siena center
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Charming House Siena center
Siena, Toscana
8% off
Price is AU$2,455
AU$2,455
AU$351 per night
includes taxes & fees
Image gallery for A luxury escape in Chianti, great landscape, stunning views, swimming pool
9.09.0 out of 10 rating
Wonderful
(19 reviews)
A luxury escape in Chianti, great landscape, stunning views, swimming pool
Greve in Chianti, Tuscany
8% off
Price is AU$3,026
AU$3,026
AU$432 per night
includes taxes & fees
Image gallery for COR MAGIS KAMULLIA 200mt from the historic center and close to the train station
9.69.6 out of 10 rating
Exceptional
(5 reviews)
COR MAGIS KAMULLIA 200mt from the historic center and close to the train station
Siena, Provincia di Siena
9% off
Price is AU$1,492
AU$1,492
AU$213 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$1,295
AU$1,295
AU$185 per night
includes taxes & fees
Image gallery for Agriturismo Il Palazzo Casa Florence
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Agriturismo Il Palazzo Casa Florence
Pergine Valdarno, Tuscany
13% off
Price is AU$1,177
AU$1,177
AU$168 per night
includes taxes & fees
Image gallery for Residence Il Palazzo_Casa Campagna
8.48.4 out of 10 rating
Very good
(5 reviews)
Residence Il Palazzo_Casa Campagna
Pergine Valdarno, Tuscany
9% off
Price is AU$1,278
AU$1,278
AU$183 per night
includes taxes & fees
Image gallery for La Vecchia Posta | Charming home near Chianti and Art Cities – 2 Beds, 3 Baths
1010 out of 10 rating
Exceptional
(10 reviews)
La Vecchia Posta | Charming home near Chianti and Art Cities – 2 Beds, 3 Baths
Cavriglia, Toscana
24% off
Price is AU$2,217
AU$2,217
AU$317 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Il Cassero
Farmhouse in the heart of the real chiantishire
Sleeps 4 · 2 bedrooms
1010 out of 10
Exceptionalexceptional
137 reviews(137 reviews)
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Sleeps 23 · 11 bedrooms · 11+ bathrooms
1010 out of 10
Exceptionalexceptional
57 reviews(57 reviews)
Beautiful stone house with garden and private pool.
Sleeps 5 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
60 reviews(60 reviews)
Traditional Tuscan farmhouse with stunning views
Sleeps 8 · 3 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
95 reviews(95 reviews)
MAGNIFICENT 9BR VILLA WITH HEATED POOL & STUNNING VIEWS IN TOP CHIANTI LOCATION!
Sleeps 18 · 9 bedrooms · 7+ bathrooms
1010 out of 10
Exceptionalexceptional
40 reviews(40 reviews)
Beautiful house on Chianti hilltop with exceptional views.
Sleeps 8 · 4 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Top rated rentals - Il Cassero
Amazing house like a dream.
1010 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Fabulous in Chianti
1010 out of 10
Exceptionalexceptional
57 reviews(57 reviews)
Beautiful farmhouse in Chianti
1010 out of 10
Exceptionalexceptional
137 reviews(137 reviews)
The highlight of our travels in Tuscany
1010 out of 10
Exceptionalexceptional
121 reviews(121 reviews)
Amazing!!
1010 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
Loved our Tuscan villa!
1010 out of 10
Exceptionalexceptional
142 reviews(142 reviews)
A slice of Tuscan heaven
1010 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
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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