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 AU$45,886
AU$45,886
AU$6,555 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 AU$21,621
AU$21,621
AU$3,089 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 AU$12,415
AU$12,415
AU$1,774 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
14% off
Price is AU$17,478
AU$17,478
AU$2,497 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 AU$4,085
AU$4,085
AU$584 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 AU$17,990
AU$17,990
AU$2,570 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 AU$5,632
AU$5,632
AU$805 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
14% off
Price is AU$9,461
AU$9,461
AU$1,352 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 AU$19,577
AU$19,577
AU$2,797 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 AU$5,978
AU$5,978
AU$854 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$14,476
AU$14,476
AU$2,068 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 AU$7,951
AU$7,951
AU$1,136 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 AU$2,033
AU$2,033
AU$290 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 AU$6,806
AU$6,806
AU$972 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 AU$2,959
AU$2,959
AU$423 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 AU$1,307
AU$1,307
AU$187 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 AU$11,618
AU$11,618
AU$1,660 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 AU$1,727
AU$1,727
AU$247 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 AU$1,224
AU$1,224
AU$175 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 AU$1,601
AU$1,601
AU$229 per night
includes taxes & fees
Image gallery for Typical Tuscan Countryside Cottage near Florence
1010 out of 10 rating
Exceptional
(28 reviews)
Typical Tuscan Countryside Cottage near Florence
Bagno a Ripoli, Tuscany
6% off
Price is AU$2,367
AU$2,367
AU$338 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 AU$3,734
AU$3,734
AU$533 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
14% off
Price is AU$1,958
AU$1,958
AU$280 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 AU$1,092
AU$1,092
AU$156 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
Showing deals for: 31 Oct - 3 Nov
Ancient farm situated in the heart of the Chianti Classico Senese, Pool and View
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
90 reviews(90 reviews)
The current price is AU$874
AU$874
for 3 nights, 1 home
AU$291 per night
includes taxes & fees
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
49 reviews(49 reviews)
The current price is AU$800
AU$800
for 3 nights, 1 apartment
AU$267 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
8.88.8 out of 10
Excellentexcellent
20 reviews(20 reviews)
The current price is AU$965
AU$965
for 3 nights, 1 home
AU$322 per night
includes taxes & fees
CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
Sleeps 4 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
26 reviews(26 reviews)
The current price is AU$1,186
AU$1,186
for 3 nights, 1 room
AU$395 per night
includes taxes & fees
Villa with large garden in the Chianti hills
Sleeps 5 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
70 reviews(70 reviews)
The current price is AU$638
AU$638
for 3 nights, 1 home
AU$213 per night
includes taxes & fees
Family apartment with magical view on the old city, balcony, wifi & parking
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
56 reviews(56 reviews)
The current price is AU$1,065
AU$1,065
for 3 nights, 1 apartment
AU$355 per night
includes taxes & fees
Top rated rentals - Il Cassero
Amazing
1010 out of 10
Exceptionalexceptional
140 reviews(140 reviews)
A slice of Tuscan heaven
1010 out of 10
Exceptionalexceptional
66 reviews(66 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