Holiday rentals near Il Cassero
We found 3,811 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:18 Jul - 25 Jul
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 NZ$15,496
NZ$15,496
NZ$2,214 per night
includes taxes & fees
Image gallery for Affittacamere Maria Gabriella, B&B and Holiday Home in Val d'Orcia
9.89.8 out of 10 rating
Exceptional
(39 reviews)
Affittacamere Maria Gabriella, B&B and Holiday Home in Val d'Orcia
Pienza, Tuscany
9% off
Price is NZ$9,224
NZ$9,224
NZ$1,318 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 NZ$4,658
NZ$4,658
NZ$665 per night
includes taxes & fees
Image gallery for Rhythms and atmospheres of the past, the comforts of the present a stone's throw from the city
1010 out of 10 rating
Exceptional
(25 reviews)
Rhythms and atmospheres of the past, the comforts of the present a stone's throw from the city
Arezzo, Toscana
5% off
Price is NZ$2,382
NZ$2,382
NZ$340 per night
includes taxes & fees
Image gallery for Elegant country barn in Cortona 2bed2bath with shared pool & gorgeous gardens
1010 out of 10 rating
Exceptional
(21 reviews)
Elegant country barn in Cortona 2bed2bath with shared pool & gorgeous gardens
Cortona, Tuscany
7% off
Price is NZ$4,769
NZ$4,769
NZ$681 per night
includes taxes & fees
Image gallery for Apartment/house in a Tuscan stonehouse with private swimming pool and garden
9.49.4 out of 10 rating
Exceptional
(36 reviews)
Apartment/house in a Tuscan stonehouse with private swimming pool and garden
Cortona, Tuscany
18% off
Price is NZ$1,791
NZ$1,791
NZ$256 per night
includes taxes & fees
Image gallery for Villa Mulinello, secluded, panoramic view over Montepulciano valley.
1010 out of 10 rating
Exceptional
(33 reviews)
Villa Mulinello, secluded, panoramic view over Montepulciano valley.
Torrita di Siena, Tuscany
9% off
Price is NZ$3,659
NZ$3,659
NZ$523 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 NZ$2,619
NZ$2,619
NZ$374 per night
includes taxes & fees
Image gallery for Cottage " I due Pini"
1010 out of 10 rating
Exceptional
(36 reviews)
Cottage " I due Pini"
Cortona, Provincia di Arezzo
9% off
Price is NZ$1,143
NZ$1,143
NZ$163 per night
includes taxes & fees
Image gallery for House / Villa - Monteroni d'Arbia
9.89.8 out of 10 rating
Exceptional
(6 reviews)
House / Villa - Monteroni d'Arbia
Monteroni d'Arbia, Tuscany
8% off
Price is NZ$12,219
NZ$12,219
NZ$1,746 per night
includes taxes & fees
Image gallery for Manor Villa with private pool and SPA surrounded by greenery
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Manor Villa with private pool and SPA surrounded by greenery
Montalcino, Provincia di Siena
10% off
Price is NZ$18,670
NZ$18,670
NZ$2,667 per night
includes taxes & fees
Image gallery for Apartment in the old town with 2 bedrooms, 2 bathroom and a large terrace
1010 out of 10 rating
Exceptional
(5 reviews)
Apartment in the old town with 2 bedrooms, 2 bathroom and a large terrace
Arezzo, Toscana
12% off
Price is NZ$2,118
NZ$2,118
NZ$303 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 NZ$1,577
NZ$1,577
NZ$225 per night
includes taxes & fees
Image gallery for Cortona Suite: The palace with frescoes - Cortona's Frescos Palace
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Cortona Suite: The palace with frescoes - Cortona's Frescos Palace
Cortona, Provincia di Arezzo
14% off
Price is NZ$4,645
NZ$4,645
NZ$664 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 NZ$2,783
NZ$2,783
NZ$398 per night
includes taxes & fees
Image gallery for Cozy house in the heart of Tuscany near Chianti and the cities of art
1010 out of 10 rating
Exceptional
(10 reviews)
Cozy house in the heart of Tuscany near Chianti and the cities of art
Cavriglia, Toscana
8% off
Price is NZ$2,924
NZ$2,924
NZ$418 per night
includes taxes & fees
Image gallery for Farm between Florence and Arezzo home Pratomagno
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Farm between Florence and Arezzo home Pratomagno
Pergine Valdarno, Tuscany
13% off
Price is NZ$1,444
NZ$1,444
NZ$206 per night
includes taxes & fees
Image gallery for Residence Le Chiuse -Casa Gialla
1010 out of 10 rating
Exceptional
(5 reviews)
Residence Le Chiuse -Casa Gialla
Montevarchi
13% off
Price is NZ$1,481
NZ$1,481
NZ$212 per night
includes taxes & fees
Image gallery for Apartment Me and You Cortona (with romantic outdoor shower on private courtyard)
1010 out of 10 rating
Exceptional
(16 reviews)
Apartment Me and You Cortona (with romantic outdoor shower on private courtyard)
Cortona, Tuscany
9% off
Price is NZ$1,850
NZ$1,850
NZ$264 per night
includes taxes & fees
Image gallery for CHARMING HOUSE IN HISTORIC TOWN CENTRE - ART-STUDIO In Cerca D'Autore
1010 out of 10 rating
Exceptional
(72 reviews)
CHARMING HOUSE IN HISTORIC TOWN CENTRE - ART-STUDIO In Cerca D'Autore
Montepulciano, Toscana
9% off
Price is NZ$4,419
NZ$4,419
NZ$631 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 NZ$16,613
NZ$16,613
NZ$2,373 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
13% off
Price is NZ$1,825
NZ$1,825
NZ$261 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 NZ$1,991
NZ$1,991
NZ$284 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Il Cassero
Traditional stone cottage in rural, tranquil and quiet location built in 1799
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
39 reviews(39 reviews)
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Sleeps 7 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
115 reviews(115 reviews)
Farmhouse in the hills with panoramic view and swimming pool
Sleeps 10 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
67 reviews(67 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)
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Sleeps 5 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
65 reviews(65 reviews)
House / Villa - Monte San Savino
Sleeps 5 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Top rated rentals - Il Cassero
Fabulous Experience
1010 out of 10
Exceptionalexceptional
46 reviews(46 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
More for lessMore space, more privacy, more amenities — more value