Holiday rentals near Il Cassero
We found 3,898 holiday rentals — enter your dates for availability
Select the perfect private holiday rental within easy reach of Il Cassero. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as Wi-Fi and a hot tub. You'll be sure to find a property to rent to meet everyone's 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$13,758
AU$13,758
AU$1,965 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$7,119
AU$7,119
AU$1,017 per night
includes taxes & fees
Image gallery for SIGNORELLI HOUSE soundproofed apartment in the historic center
1010 out of 10 rating
Exceptional
(9 reviews)
SIGNORELLI HOUSE soundproofed apartment in the historic center
Cortona, Tuscany
28% off
Price is AU$5,272
AU$5,272
AU$753 per night
includes taxes & fees
Image gallery for Case Ginezzo: The Farm and the Refuge. Cortona
8.68.6 out of 10 rating
Excellent
(9 reviews)
Case Ginezzo: The Farm and the Refuge. Cortona
Cortona, Tuscany
9% off
Price is AU$6,952
AU$6,952
AU$993 per night
includes taxes & fees
Image gallery for Villa with private pool, whirlpool, sauna and last minute discounts
8.48.4 out of 10 rating
Very good
(9 reviews)
Villa with private pool, whirlpool, sauna and last minute discounts
Foiano della Chiana, Arezzo
22% off
Price is AU$7,019
AU$7,019
AU$1,003 per night
includes taxes & fees
Image gallery for Agriturismo Il Salarco: Apartment
9.69.6 out of 10 rating
Exceptional
(12 reviews)
Agriturismo Il Salarco: Apartment
Montepulciano, Tuscany
9% off
Price is AU$1,746
AU$1,746
AU$249 per night
includes taxes & fees
Image gallery for Romantic cottage on a farm with a view of Cortona
1010 out of 10 rating
Exceptional
(8 reviews)
Romantic cottage on a farm with a view of Cortona
Cortona, Tuscany
5% off
Price is AU$2,432
AU$2,432
AU$347 per night
includes taxes & fees
Image gallery for Villa Mulinello, secluded, panoramic view over Montepulciano valley.
1010 out of 10 rating
Exceptional
(34 reviews)
Villa Mulinello, secluded, panoramic view over Montepulciano valley.
Torrita di Siena, Tuscany
9% off
Price is AU$3,156
AU$3,156
AU$451 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$1,213
AU$1,213
AU$173 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
(7 reviews)
Casa di Sotto, Podere Ampella: a beautiful holiday house in the heart of Tuscany
Montalcino, Siena
9% off
Price is AU$3,833
AU$3,833
AU$548 per night
includes taxes & fees
Image gallery for Large shining148sqmt wififiber apartment, view and free parking in Montepulciano
1010 out of 10 rating
Exceptional
(10 reviews)
Large shining148sqmt wififiber apartment, view and free parking in Montepulciano
Montepulciano, Provincia di Siena
20% off
Price is AU$1,634
AU$1,634
AU$233 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$1,753
AU$1,753
AU$250 per night
includes taxes & fees
Image gallery for Villa Maria 3 floors (detached - garage)
1010 out of 10 rating
Exceptional
(5 reviews)
Villa Maria 3 floors (detached - garage)
Sinalunga, Provincia di Siena
11% off
Price is AU$1,319
AU$1,319
AU$188 per night
includes taxes & fees
Image gallery for old barn on Via Francigena
9.89.8 out of 10 rating
Exceptional
(11 reviews)
old barn on Via Francigena
Siena, Toscana
13% off
Price is AU$1,539
AU$1,539
AU$220 per night
includes taxes & fees
Image gallery for Dream vacation home in an absolutely peaceful location
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Dream vacation home in an absolutely peaceful location
Sinalunga, Siena
9% off
Price is AU$5,231
AU$5,231
AU$747 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$1,290
AU$1,290
AU$184 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$1,273
AU$1,273
AU$182 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
23% off
Price is AU$1,927
AU$1,927
AU$275 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$1,173
AU$1,173
AU$168 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$18,233
AU$18,233
AU$2,605 per night
includes taxes & fees
Image gallery for Residence Le Chiuse - Casa Verde
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Residence Le Chiuse - Casa Verde
Montevarchi
13% off
Price is AU$1,130
AU$1,130
AU$161 per night
includes taxes & fees
Image gallery for Farmhouse Il Palazzo Casa Chianti
8.08.0 out of 10 rating
Very good
(8 reviews)
Farmhouse Il Palazzo Casa Chianti
Pergine Valdarno, Tuscany
12% off
Price is AU$1,058
AU$1,058
AU$151 per night
includes taxes & fees
Image gallery for Villa with private pool, air conditioning, 4km from town, 30km Siena & Arezzo
1010 out of 10 rating
Exceptional
(26 reviews)
Villa with private pool, air conditioning, 4km from town, 30km Siena & Arezzo
Lucignano, Toscana
10% off
Price is AU$5,262
AU$5,262
AU$752 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Il Cassero
Tuscany as it once was
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
Farmhouse in the hills with panoramic view and swimming pool
Sleeps 10 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
69 reviews(69 reviews)
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Sleeps 5 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
67 reviews(67 reviews)
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Sleeps 7 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
121 reviews(121 reviews)
Casina in authentic Tuscany
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
62 reviews(62 reviews)
House with garden and panoramic view over Lake Trasimeno
Sleeps 9 · 4 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
Top rated rentals - Il Cassero
Loved Our Stay In Montepulciano
1010 out of 10
Exceptionalexceptional
78 reviews(78 reviews)
Beautiful stay
1010 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
Private villa with private pool close to Montisi.
1010 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
Great place
1010 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
The highlight of our travels in Tuscany
1010 out of 10
Exceptionalexceptional
121 reviews(121 reviews)
Rustic Charm
1010 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
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
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