Holiday rentals near Il Cassero
We found 3,983 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:31 Oct - 7 Nov
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 NZ$53,959
NZ$53,959
NZ$7,708 per night
includes taxes & fees
Image gallery for Medieval Castle 15 km from Florence, in the heart of "Chianti Classico" region
1010 out of 10 rating
Exceptional
(23 reviews)
Medieval Castle 15 km from Florence, in the heart of "Chianti Classico" region
Greve in Chianti, Toscana
9% off
Price is NZ$24,578
NZ$24,578
NZ$3,511 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
7% off
Price is NZ$13,866
NZ$13,866
NZ$1,981 per night
includes taxes & fees
Image gallery for Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo
1010 out of 10 rating
Exceptional
(16 reviews)
Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo
Arezzo, Tuscany
13% off
Price is NZ$20,653
NZ$20,653
NZ$2,950 per night
includes taxes & fees
Image gallery for Gorgeous villa with new pool in the heart of Chianti (wi fi and whirlpool)
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Gorgeous villa with new pool in the heart of Chianti (wi fi and whirlpool)
Radda in Chianti, Toscana
8% off
Price is NZ$4,486
NZ$4,486
NZ$641 per night
includes taxes & fees
Image gallery for Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
1010 out of 10 rating
Exceptional
(9 reviews)
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Radda in Chianti, Provincia di Siena
5% off
Price is NZ$20,351
NZ$20,351
NZ$2,907 per night
includes taxes & fees
Image gallery for Villa in the Heart of Chianti
1010 out of 10 rating
Exceptional
(36 reviews)
Villa in the Heart of Chianti
Greve in Chianti, Tuscany
14% off
Price is NZ$6,138
NZ$6,138
NZ$877 per night
includes taxes & fees
Image gallery for Large estate with private pool comprising 7 apartments - up to 24 people
9.49.4 out of 10 rating
Exceptional
(36 reviews)
Large estate with private pool comprising 7 apartments - up to 24 people
Greve in Chianti, Toscana
13% off
Price is NZ$10,843
NZ$10,843
NZ$1,549 per night
includes taxes & fees
Image gallery for Camparone, ArcenoRentalsClub Magnificent Chianti Villa Exclusive Pool Concierge
1010 out of 10 rating
Exceptional
(19 reviews)
Camparone, ArcenoRentalsClub Magnificent Chianti Villa Exclusive Pool Concierge
Castelnuovo Berardenga, Provincia di Siena
14% off
Price is NZ$22,198
NZ$22,198
NZ$3,171 per night
includes taxes & fees
Image gallery for Villa Montanina - Relax in Tuscany
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Villa Montanina - Relax in Tuscany
Castel Focognano, Tuscany
14% off
Price is NZ$6,542
NZ$6,542
NZ$935 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$16,278
NZ$16,278
NZ$2,325 per night
includes taxes & fees
Image gallery for FABULOUS 6BR HOME WITH WONDERFUL SWIMMING POOL & GARDEN IN THE HEART OF TUSCANY!
1010 out of 10 rating
Exceptional
(20 reviews)
FABULOUS 6BR HOME WITH WONDERFUL SWIMMING POOL & GARDEN IN THE HEART OF TUSCANY!
Lucignano, Tuscany
9% off
Price is NZ$8,618
NZ$8,618
NZ$1,231 per night
includes taxes & fees
Image gallery for House in Chianti - La Capanna
1010 out of 10 rating
Exceptional
(5 reviews)
House in Chianti - La Capanna
Greve in Chianti, Tuscany
9% off
Price is NZ$2,231
NZ$2,231
NZ$319 per night
includes taxes & fees
Image gallery for Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool & Spa
1010 out of 10 rating
Exceptional
(146 reviews)
Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool & Spa
Castellina in Chianti, Tuscany
9% off
Price is NZ$7,397
NZ$7,397
NZ$1,057 per night
includes taxes & fees
Image gallery for Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
9.89.8 out of 10 rating
Exceptional
(44 reviews)
Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
Castelnuovo Berardenga, Tuscany
14% off
Price is NZ$3,251
NZ$3,251
NZ$464 per night
includes taxes & fees
Image gallery for Special offer Newly renovated fine detached villa with fireplace.
8.68.6 out of 10 rating
Excellent
(11 reviews)
Special offer Newly renovated fine detached villa with fireplace.
Castelnuovo Berardenga, Tuscany
8% off
Price is NZ$1,447
NZ$1,447
NZ$207 per night
includes taxes & fees
Image gallery for BEAUTIFUL VILLA with private Pool in the heart of Chianti
1010 out of 10 rating
Exceptional
(24 reviews)
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Castelnuovo Berardenga
6% off
Price is NZ$12,997
NZ$12,997
NZ$1,857 per night
includes taxes & fees
Image gallery for Purgatorio house, a typical Tuscan structure with pool, surrounded by nature.
1010 out of 10 rating
Exceptional
(9 reviews)
Purgatorio house, a typical Tuscan structure with pool, surrounded by nature.
Ortignano Raggiolo, Tuscany
8% off
Price is NZ$1,898
NZ$1,898
NZ$271 per night
includes taxes & fees
Image gallery for Typical Tuscan Residence near the farm la Vialla
9.09.0 out of 10 rating
Wonderful
(10 reviews)
Typical Tuscan Residence near the farm la Vialla
Capolona, Toscana
8% off
Price is NZ$1,356
NZ$1,356
NZ$194 per night
includes taxes & fees
Image gallery for Enjoy peace in the heart of the Chianti Classico
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Enjoy peace in the heart of the Chianti Classico
Greve in Chianti, Toscana
6% off
Price is NZ$1,760
NZ$1,760
NZ$251 per night
includes taxes & fees
Image gallery for Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment
9.29.2 out of 10 rating
Wonderful
(25 reviews)
Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment
Civitella in Val di Chiana, Province of Arezzo
8% off
Price is NZ$4,100
NZ$4,100
NZ$586 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 NZ$2,150
NZ$2,150
NZ$307 per night
includes taxes & fees
Image gallery for Majestic Farmhouse with Pool
1010 out of 10 rating
Exceptional
(5 reviews)
Majestic Farmhouse with Pool
Loro Ciuffenna
8% off
Price is NZ$1,194
NZ$1,194
NZ$171 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$4,049
NZ$4,049
NZ$578 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
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
140 reviews(140 reviews)
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Sleeps 23 · 11 bedrooms · 11+ bathrooms
1010 out of 10
Exceptionalexceptional
60 reviews(60 reviews)
Traditional Tuscan farmhouse with stunning views
Sleeps 8 · 3 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
97 reviews(97 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
66 reviews(66 reviews)
Beautiful stone house with garden and private pool.
Sleeps 5 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
63 reviews(63 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