Holiday rentals near Il Cassero
We found 3,915 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:14 Nov - 21 Nov
Image gallery for Winery Villa in the heart of Nobile Vineyards.
1010 out of 10 rating
Exceptional
(14 reviews)
Winery Villa in the heart of Nobile Vineyards.
Montepulciano, Toscana
9% off
Price is AU$5,826
AU$5,826
AU$832 per night
includes taxes & fees
Image gallery for Chiusarella Arceno Rentals Club Chianti Villa exclusive Pool Concierge freeWiFi
1010 out of 10 rating
Exceptional
(33 reviews)
Chiusarella Arceno Rentals Club Chianti Villa exclusive Pool Concierge freeWiFi
Castelnuovo Berardenga, Tuscany
14% off
Price is AU$14,547
AU$14,547
AU$2,078 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
(17 reviews)
Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo
Arezzo, Tuscany
14% off
Price is AU$15,123
AU$15,123
AU$2,160 per night
includes taxes & fees
Image gallery for Villa Poggio del Sole, 8-10 Pax, Private Pool, Air Conditioned
1010 out of 10 rating
Exceptional
(7 reviews)
Villa Poggio del Sole, 8-10 Pax, Private Pool, Air Conditioned
Cortona, Provincia di Arezzo
9% off
Price is AU$7,867
AU$7,867
AU$1,124 per night
includes taxes & fees
Image gallery for Apartment in Farmhouse
1010 out of 10 rating
Exceptional
(5 reviews)
Apartment in Farmhouse
Cortona, Tuscany
6% off
Price is AU$1,694
AU$1,694
AU$242 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
(12 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 AU$24,056
AU$24,056
AU$3,437 per night
includes taxes & fees
Image gallery for Apartment in renovated farmhouse in typical Chianti Tuscan village
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Apartment in renovated farmhouse in typical Chianti Tuscan village
Castelnuovo Berardenga, Toscana
7% off
Price is AU$1,753
AU$1,753
AU$250 per night
includes taxes & fees
Image gallery for FARMH. PODERE CUNINA 25 KM SUD SIENA / MONTALCINO PRENDENDO LEZIONI DI CUCINA
1010 out of 10 rating
Exceptional
(19 reviews)
FARMH. PODERE CUNINA 25 KM SUD SIENA / MONTALCINO PRENDENDO LEZIONI DI CUCINA
Buonconvento
8% off
Price is AU$2,123
AU$2,123
AU$303 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$19,673
AU$19,673
AU$2,810 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$7,072
AU$7,072
AU$1,010 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$7,990
AU$7,990
AU$1,141 per night
includes taxes & fees
Image gallery for Luxury Villa in Monticchiello, your heaven in Tuscany
1010 out of 10 rating
Exceptional
(53 reviews)
Luxury Villa in Monticchiello, your heaven in Tuscany
Pienza, Toscana
17% off
Price is AU$1,505
AU$1,505
AU$215 per night
includes taxes & fees
Image gallery for Idyllic guest house in Tuscan country house style with swimming pool
1010 out of 10 rating
Exceptional
(23 reviews)
Idyllic guest house in Tuscan country house style with swimming pool
Sinalunga, Siena
9% off
Price is AU$2,084
AU$2,084
AU$298 per night
includes taxes & fees
Image gallery for Large country apartment in Cortona 1bed1bath with shared pool & gorgeous gardens
1010 out of 10 rating
Exceptional
(12 reviews)
Large country apartment in Cortona 1bed1bath with shared pool & gorgeous gardens
Cortona, Tuscany
7% off
Price is AU$2,120
AU$2,120
AU$303 per night
includes taxes & fees
Image gallery for Agriturismo Il Salarco: Apartment
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Agriturismo Il Salarco: Apartment
Montepulciano, Tuscany
9% off
Price is AU$1,860
AU$1,860
AU$266 per night
includes taxes & fees
Image gallery for Villa Banditello, secluded, panoramic view over Montepulciano valley.
1010 out of 10 rating
Exceptional
(24 reviews)
Villa Banditello, secluded, panoramic view over Montepulciano valley.
Torrita di Siena, Tuscany
9% off
Price is AU$2,996
AU$2,996
AU$428 per night
includes taxes & fees
Image gallery for Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga
Cortona, Tuscany
18% off
Price is AU$5,222
AU$5,222
AU$746 per night
includes taxes & fees
Image gallery for Typical Tuscan Residence near the farm la Vialla
9.29.2 out of 10 rating
Wonderful
(11 reviews)
Typical Tuscan Residence near the farm la Vialla
Capolona, Toscana
8% off
Price is AU$1,230
AU$1,230
AU$176 per night
includes taxes & fees
Image gallery for "Gabolandia", a holiday home in Cortona
9.49.4 out of 10 rating
Exceptional
(6 reviews)
"Gabolandia", a holiday home in Cortona
Cortona, Tuscany
8% off
Price is AU$2,133
AU$2,133
AU$305 per night
includes taxes & fees
Image gallery for Montalcino,private villa with pool in Tuscany,stunning wiews!
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Montalcino,private villa with pool in Tuscany,stunning wiews!
Montalcino, Tuscany
22% off
Price is AU$7,932
AU$7,932
AU$1,133 per night
includes taxes & fees
Image gallery for Tuscan Villa private infinity pool, exclusive location, AC, extra services
1010 out of 10 rating
Exceptional
(61 reviews)
Tuscan Villa private infinity pool, exclusive location, AC, extra services
Cortona, ar
9% off
Price is AU$4,950
AU$4,950
AU$707 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 AU$4,440
AU$4,440
AU$634 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$2,436
AU$2,436
AU$348 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Il Cassero
Farmhouse in the hills with panoramic view and swimming pool
Sleeps 10 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
71 reviews(71 reviews)
Tuscany as it once was
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Sleeps 5 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
69 reviews(69 reviews)
Luxury Peaceful Villa With Vine Covered Pergola Enjoying Panoramic Views.
Sleeps 14 · 6 bedrooms · 5+ bathrooms
1010 out of 10
Exceptionalexceptional
38 reviews(38 reviews)
17th century farmhouse with private pool and Wi-Fi and air conditioning
Sleeps 10 · 4 bedrooms · 4 bathrooms
9.49.4 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
Luxury Cortona view hilltop Villa
Sleeps 12 · 6 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
Top rated rentals - Il Cassero
What a Villa in Tuscany is all about.
1010 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
Perfect location for day trips covering so many of the hilltop towns. Perfect accommodation for a group of 12 friends as each bedroom has it’s own bathroom.Perfect Villa for relaxing at home coffee every morning, lying by the pool and dinner watching the incredible sunsets.Perfect hosts. Denise takes care of everything while you are at the villa including cooking us a wonderful dinner. Mieke answered all our questions prior to our arrival very promptly. She has set the villa up perfectly and send out an excellent guide book to answer nearly all your questions.
Belinda P.
Stayed May 2025
Beautiful stay
1010 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
We received a warm welcome from the family and a thorough explanation of the facilities, the surrounding area and places of interest. Fabrizio communicated easily with us using the translation phone app. The apartment is very clean, well equipped and offers a genuine Italian experience. Simply wonderful.
Murray H.
Stayed Oct 2024
Hilltop magic
1010 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
Sadly my husband and I were not able to join our adult children for our family holiday. But so glad our children continued on and had a wonderful time with their partners. The host was incredibly understanding and regularly communicated. We plan to go next year!
Serena L.
Stayed Aug 2023
Rustic Charm
1010 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
The property was homely, rustic and welcoming.
The owners did everything to make us comfortable with their own produce and wine.
Liz and Martyn R.
Stayed July 2023
Fabulous in every way
1010 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
Just divine location, magnificent view...friendly hosts and lovely Tuscan house. We loved our stay with our 8 month old baby!
Stephanie B.
Stayed May 2019
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