Holiday rentals near Il Cassero
We found 3,838 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:8 Aug - 15 Aug
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$15,440
NZ$15,440
NZ$2,206 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$22,648
NZ$22,648
NZ$3,235 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$9,190
NZ$9,190
NZ$1,313 per night
includes taxes & fees
Image gallery for Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.
1010 out of 10 rating
Exceptional
(10 reviews)
Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.
San Giovanni d'Asso, Provincia di Siena
9% off
Price is NZ$26,461
NZ$26,461
NZ$3,780 per night
includes taxes & fees
Image gallery for Il Saragio open space in the Tuscan countryside
1010 out of 10 rating
Exceptional
(4 reviews)
Il Saragio open space in the Tuscan countryside
Montepulciano, Toscana
9% off
Price is NZ$1,395
NZ$1,395
NZ$199 per night
includes taxes & fees
Image gallery for SIGNORELLI HOUSE soundproofed apartment in the historic center
1010 out of 10 rating
Exceptional
(8 reviews)
SIGNORELLI HOUSE soundproofed apartment in the historic center
Cortona, Tuscany
28% off
Price is NZ$5,749
NZ$5,749
NZ$821 per night
includes taxes & fees
Image gallery for Appartamento Stefy, Cortona, in the old town typical Tuscan
1010 out of 10 rating
Exceptional
(17 reviews)
Appartamento Stefy, Cortona, in the old town typical Tuscan
Cortona, Toscana
14% off
Price is NZ$1,556
NZ$1,556
NZ$222 per night
includes taxes & fees
Image gallery for The Old Fashion House
1010 out of 10 rating
Exceptional
(5 reviews)
The Old Fashion House
Cortona, Provincia di Arezzo
8% off
Price is NZ$2,004
NZ$2,004
NZ$286 per night
includes taxes & fees
Image gallery for Cozy renovated rustic house nestled in the Tuscan countryside
1010 out of 10 rating
Exceptional
(18 reviews)
Cozy renovated rustic house nestled in the Tuscan countryside
Lucignano, Arezzo
9% off
Price is NZ$1,723
NZ$1,723
NZ$246 per night
includes taxes & fees
Image gallery for WI FI FIBER Cozy Studio with "Trunk"
1010 out of 10 rating
Exceptional
(24 reviews)
WI FI FIBER Cozy Studio with "Trunk"
Montepulciano, Provincia di Siena
20% off
Price is NZ$873
NZ$873
NZ$125 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$1,633
NZ$1,633
NZ$233 per night
includes taxes & fees
Image gallery for Agriturismo Il Palazzo Casa Florence
1010 out of 10 rating
Exceptional
(5 reviews)
Agriturismo Il Palazzo Casa Florence
Pergine Valdarno, Tuscany
13% off
Price is NZ$1,942
NZ$1,942
NZ$277 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
10% off
Price is NZ$1,988
NZ$1,988
NZ$284 per night
includes taxes & fees
Image gallery for La Vecchia Posta | Tuscan Charm between Chianti and Art Cities
1010 out of 10 rating
Exceptional
(10 reviews)
La Vecchia Posta | Tuscan Charm between Chianti and Art Cities
Cavriglia, Toscana
8% off
Price is NZ$2,395
NZ$2,395
NZ$342 per night
includes taxes & fees
Image gallery for Apartment in a medieval village
9.09.0 out of 10 rating
Wonderful
(9 reviews)
Apartment in a medieval village
San Giovanni d'Asso, Toscana
8% off
Price is NZ$1,188
NZ$1,188
NZ$170 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$1,439
NZ$1,439
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$1,475
NZ$1,475
NZ$211 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$1,433
NZ$1,433
NZ$205 per night
includes taxes & fees
Image gallery for Classic Stunning 3 Bedroom Apartment in Montepulciano with Air Conditioning,
1010 out of 10 rating
Exceptional
(33 reviews)
Classic Stunning 3 Bedroom Apartment in Montepulciano with Air Conditioning,
Montepulciano, Toscana
23% off
Price is NZ$5,113
NZ$5,113
NZ$730 per night
includes taxes & fees
Image gallery for LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center
9.69.6 out of 10 rating
Exceptional
(40 reviews)
LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center
Montepulciano, Tuscany
8% off
Price is NZ$1,364
NZ$1,364
NZ$195 per night
includes taxes & fees
Image gallery for Residence Le Chiuse -Casa Marrone
1010 out of 10 rating
Exceptional
(15 reviews)
Residence Le Chiuse -Casa Marrone
Montevarchi
13% off
Price is NZ$2,201
NZ$2,201
NZ$314 per night
includes taxes & fees
Image gallery for Residence Il Palazzo_Casa Siena
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Residence Il Palazzo_Casa Siena
Pergine Valdarno, Tuscany
13% off
Price is NZ$1,942
NZ$1,942
NZ$277 per night
includes taxes & fees
Image gallery for HillsideVilla overlooking the Tuscan landscape between Florence Arezzo and Siena
1010 out of 10 rating
Exceptional
(27 reviews)
HillsideVilla overlooking the Tuscan landscape between Florence Arezzo and Siena
Loro Ciuffenna, Tuscany
8% off
Price is NZ$2,701
NZ$2,701
NZ$386 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)
Farmhouse in the hills with panoramic view and swimming pool
Sleeps 10 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
68 reviews(68 reviews)
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Sleeps 7 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
116 reviews(116 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)
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)
Tuscany as it once was
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
Top rated rentals - Il Cassero
Fabulous Experience
1010 out of 10
Exceptionalexceptional
47 reviews(47 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