
Holiday rentals near Torre Il Cassero
We found 4,188 holiday rentals — enter your dates for availability
If you are looking to stay near Torre Il Cassero, scroll through and discover private holiday rentals to find the perfect home base for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and garden. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Torre Il Cassero
Showing deals for:7 Nov - 14 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 £2,917
£2,917
£417 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 £1,071
£1,071
£153 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
8% off
Price is £4,012
£4,012
£573 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 £3,952
£3,952
£565 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
13% off
Price is £7,741
£7,741
£1,106 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 £3,560
£3,560
£509 per night
includes taxes & fees
Image gallery for WP RELAIS BORGO VIGNALUNGA, 46 HECTARES OF LAND IN THE HEART OF VAL D'ORCIA

1010 out of 10 rating
Exceptional
(36 reviews)
WP RELAIS BORGO VIGNALUNGA, 46 HECTARES OF LAND IN THE HEART OF VAL D'ORCIA
Castiglione d'Orcia, Provincia di Siena
13% off
Price is £4,588
£4,588
£655 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 £12,154
£12,154
£1,736 per night
includes taxes & fees
Image gallery for Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena

1010 out of 10 rating
Exceptional
(17 reviews)
Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena
Montepulciano
9% off
Price is £3,177
£3,177
£454 per night
includes taxes & fees
Image gallery for Chianti Villa mx10 secluded hilltopTuscan farmhouse sunset views very large pool

9.49.4 out of 10 rating
Exceptional
(16 reviews)
Chianti Villa mx10 secluded hilltopTuscan farmhouse sunset views very large pool
Gaiole in Chianti, Tuscany
8% off
Price is £2,686
£2,686
£384 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
(22 reviews)
Idyllic guest house in Tuscan country house style with swimming pool
Sinalunga, Siena
8% off
Price is £1,052
£1,052
£150 per night
includes taxes & fees
Image gallery for Luxury Villa With Private Infinity Pool,exclusive Wellness, Cortona 0.25 Miles

1010 out of 10 rating
Exceptional
(8 reviews)
Luxury Villa With Private Infinity Pool,exclusive Wellness, Cortona 0.25 Miles
Cortona, Italy/Tuscany
12% off
Price is £4,383
£4,383
£626 per night
includes taxes & fees
Image gallery for Casa di Sotto, Podere Ampella: a beautiful holiday house in the heart of Tuscany

1010 out of 10 rating
Exceptional
(8 reviews)
Casa di Sotto, Podere Ampella: a beautiful holiday house in the heart of Tuscany
Montalcino, Siena
9% off
Price is £1,562
£1,562
£223 per night
includes taxes & fees
Image gallery for Lake House, Farm in the hills between Arezzo Florence Siena, Garden, Pool

9.49.4 out of 10 rating
Exceptional
(9 reviews)
Lake House, Farm in the hills between Arezzo Florence Siena, Garden, Pool
Pergine Valdarno, Tuscany
12% off
Price is £649
£649
£93 per night
includes taxes & fees
Image gallery for Attractive Renovated Stone Mill House, Lovely Private Pool, Sleeps Max 5 People.

9.29.2 out of 10 rating
Wonderful
(22 reviews)
Attractive Renovated Stone Mill House, Lovely Private Pool, Sleeps Max 5 People.
Cortona, Tuscany
9% off
Price is £992
£992
£142 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 £1,883
£1,883
£269 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 £3,983
£3,983
£569 per night
includes taxes & fees
Image gallery for Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia

1010 out of 10 rating
Exceptional
(38 reviews)
Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia
Pienza, Siena
9% off
Price is £3,046
£3,046
£435 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 £2,209
£2,209
£316 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 £5,749
£5,749
£821 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 £2,474
£2,474
£353 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 £843
£843
£120 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 £1,068
£1,068
£153 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 £936
£936
£134 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Torre 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
37 reviews(37 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
36 reviews(36 reviews)
Luxury Cortona view hilltop Villa
Sleeps 12 · 6 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
Top rated rentals - Torre Il Cassero
Tuscan Haven
1010 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
Fantastic stay in beautiful property . Best villa we’ve stayed in and we’ve stayed in many. Good bathrooms and good kitchen equipment here .These two things have let other properties down. Nice quality glassware and cutlery , not the usual mismatch.
Villa is in peaceful location , yet handy for the lovely town of Montepulciano and its restaurants and supermarket .
Excellent, easy communication with Mariecristina .
Highly recommended
Melanie B.
Stayed Sept 2024
A lovely villa in a great location
1010 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
The villa is lovely and quiet just up the hill from the centre of Cortona, the walk literally takes 8-10 minutes. Plenty of parking, nice pool (a slight wasp infestation issue aside) and all the amenities you need. Supermarket is a 5 minute drive away. Rooms are all nice and upstairs has air conditioning (the master room aircon wasn’t cooling below 27 degrees but the other two bedrooms cooled nicely - it does get very hot). Luigi pops round most days to keep things ship shape. Would recommend for families or friends 4-6 people. It’s probably a challenging walk for families with young children to walk to town. .
Simon D.
Stayed Aug 2024
Perfect for us!
1010 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Possibly best equipped holiday rental we've been to! Great location in countryside with wonderful views , yet very easy access to civilisation , Autostrada and railway station - Florence 40 mins by train!
Sara is a great host helpful when needed and a mine of local information. In all we would heartily recommend it as a Tuscan base.
Paul H.
Stayed May 2024
Unique and Authentic Tuscany
1010 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Beautiful country house. Lovely
rural location with food shop and vineyard within 100metres. Very friendly and informative hosts, we learnt a bit more Italian than when we arrived! Stunning towns of Cortona and Montepulchiano close by to explore. Unique experience, cannot recommend enough! We loved it. Thank you.
Julie L.
Stayed Aug 2023
Very relaxing
1010 out of 10
Exceptionalexceptional
52 reviews(52 reviews)
Beautiful hillside location and welcoming, friendly host. The property was beautifully presented and spotlessly clean and comfortable. The gardens were gorgeous with always a place to relax in sun or shade. Loved the roof- top terrace with the view. Fabrizio, the host, was most helpful and has a good stock of wine and other essentials if needed. Highly recommended.
Sandra S.
Stayed Jun 2023
Perfect Holiday
1010 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
Casa Sant'Angelo is such a drealy place we found it very difficult to leave, one of the nicest places we have ever stayed. 3 double bedrooms all with huge beds, fine linen and aircon. We didn't use the annex, but what a lovely self contained apartment with its own kitchen and sitting room.
The pool was also perfect, and the cleanest we've had thanks to the robot cleaner and the local guy who popped in now and then when we weren't around.
You will need a car and Cortona is just a short drive away, but not really walkable for an evening meal as its on the top of a big hill!!
If you want to ditch the car, the mini market is a short walk away and it serves the best meats and cheese in the area, plus home made local dishes.
As an extra bonus we found a delightful local restaurant called Barbabi (not on Tripadvior, but they are on instagram). This was literally a short walk across a farmers field or slightly longer via the road. Feels a bit like someones back garden, but you can either splash out and fine dine or have a Pizza for 10 euros.
Thanks for having us at your beautiful farm house, I feel sure we will be back,
jamie b.
Stayed Aug 2022
Beautiful, comfortable, relaxing, and Italian countryside
1010 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
What a beautiful home full of comfort and authenticity. We thoroughly enjoyed our two week stay at Villa Caprile. The property, the house, the pool, all the accommodations met or exceeded our expectations. Our children teenagers and younger felt so at home, and we all enjoyed our stay. It was so wonderful to have this home to return to after short or long day trips to some of the most amazing places and towns that are all around. The location could not have been more perfect for the trip we planned. Thank you Dianne and Antonella and all the caretakers of the property for all your care and recommendations.
Jennifer S.
Stayed Jun 2017
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- All the privacy of homeEnjoy full kitchens, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value