
Vacation rentals near Il Cassero
We found 4,320 vacation rentals — enter your dates for availability
Discover a selection of private vacation rentals near Il Cassero that are perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the amenities you need and want for your stay, which might include a garden and hot tub. You'll be sure to find a rental for everyone's needs, including places that are non-smoking or accessible.
Vacation rentals with weekly discounts - Il Cassero
Showing deals for:Nov 14 - Nov 21
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
10% off
Price is CA $2,598
CA $2,598
CA $19,346 total
CA $19,346 total
includes taxes & fees
Image gallery for Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl

1010 out of 10 rating
Exceptional
(40 reviews)
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl
Greve in Chianti, Toscana
10% off
Price is CA $1,152
CA $1,152
CA $11,179 total
CA $11,179 total
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
21% off
Price is CA $507
CA $507
CA $5,290 total
CA $5,290 total
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
10% off
Price is CA $870
CA $870
CA $7,109 total
CA $7,109 total
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
15% off
Price is CA $1,700
CA $1,700
CA $13,333 total
CA $13,333 total
includes taxes & fees
Image gallery for Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.

1010 out of 10 rating
Exceptional
(10 reviews)
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Radda in Chianti, Provincia di Siena
5% off
Price is CA $2,128
CA $2,128
CA $15,955 total
CA $15,955 total
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
10% off
Price is CA $432
CA $432
CA $3,712 total
CA $3,712 total
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
15% off
Price is CA $2,353
CA $2,353
CA $17,459 total
CA $17,459 total
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
15% off
Price is CA $1,088
CA $1,088
CA $8,294 total
CA $8,294 total
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
7% off
Price is CA $253
CA $253
CA $2,086 total
CA $2,086 total
includes taxes & fees
Image gallery for AGRITURISMO in FLORENTINE HILLS-CHIANTI. 100% Travelers Recommend.

1010 out of 10 rating
Exceptional
(11 reviews)
AGRITURISMO in FLORENTINE HILLS-CHIANTI. 100% Travelers Recommend.
Rignano sull'Arno, Tuscany
10% off
Price is CA $360
CA $360
CA $2,967 total
CA $2,967 total
includes taxes & fees
Image gallery for BEAUTIFUL VILLA with private Pool in the heart of Chianti

1010 out of 10 rating
Exceptional
(25 reviews)
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Castelnuovo Berardenga
7% off
Price is CA $1,339
CA $1,339
CA $10,147 total
CA $10,147 total
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
10% off
Price is CA $391
CA $391
CA $3,334 total
CA $3,334 total
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
10% off
Price is CA $125
CA $125
CA $1,093 total
CA $1,093 total
includes taxes & fees
Image gallery for Beautiful Private & Luxurious Tuscan Villa Near Siena/Scenic Views/Crete Senesi

1010 out of 10 rating
Exceptional
(86 reviews)
Beautiful Private & Luxurious Tuscan Villa Near Siena/Scenic Views/Crete Senesi
Castelnuovo Berardenga
5% off
Price is CA $608
CA $608
CA $4,713 total
CA $4,713 total
includes taxes & fees
Image gallery for Tuscan village in SIena. farmhouse surrounded by garden,pool and panoramic view

1010 out of 10 rating
Exceptional
(43 reviews)
Tuscan village in SIena. farmhouse surrounded by garden,pool and panoramic view
Asciano, Toscana
5% off
Price is CA $380
CA $380
CA $3,063 total
CA $3,063 total
includes taxes & fees
Image gallery for Agriturismo San Silvestro - Your home with pool in the hills of Chianti

9.49.4 out of 10 rating
Exceptional
(25 reviews)
Agriturismo San Silvestro - Your home with pool in the hills of Chianti
Barberino Val d'Elsa, Tuscany
10% off
Price is CA $245
CA $245
CA $2,034 total
CA $2,034 total
includes taxes & fees
Image gallery for Luxury Suite in Renaissance Villa

9.49.4 out of 10 rating
Exceptional
(15 reviews)
Luxury Suite in Renaissance Villa
Bagno a Ripoli, Toscana
7% off
Price is CA $201
CA $201
CA $2,030 total
CA $2,030 total
includes taxes & fees
Image gallery for Charming Farmhouse with Private Pool among Vineyards

9.49.4 out of 10 rating
Exceptional
(50 reviews)
Charming Farmhouse with Private Pool among Vineyards
Greve in Chianti, Firenze
10% off
Price is CA $1,022
CA $1,022
CA $8,523 total
CA $8,523 total
includes taxes & fees
Image gallery for STONE HOUSE IN THE HEART OF TUSCANY WITH LARGE GARDEN AND SWIMMING POOL

1010 out of 10 rating
Exceptional
(17 reviews)
STONE HOUSE IN THE HEART OF TUSCANY WITH LARGE GARDEN AND SWIMMING POOL
Loro Ciuffenna, Tuscany
12% off
Price is CA $309
CA $309
CA $2,420 total
CA $2,420 total
includes taxes & fees
Image gallery for A Panoramic Tuscan Luxury - Villa Maria in Fronzano

1010 out of 10 rating
Exceptional
(74 reviews)
A Panoramic Tuscan Luxury - Villa Maria in Fronzano
Reggello, Toscana
5% off
Price is CA $1,946
CA $1,946
CA $14,489 total
CA $14,489 total
includes taxes & fees
Image gallery for Serena al Casalone, Design apartment in Private Chianti Estate, pool WIFI A/C

9.69.6 out of 10 rating
Exceptional
(5 reviews)
Serena al Casalone, Design apartment in Private Chianti Estate, pool WIFI A/C
Castelnuovo Berardenga, Toscana
15% off
Price is CA $564
CA $564
CA $4,333 total
CA $4,333 total
includes taxes & fees
Image gallery for Beautifully restored farmhouse in Greve, heart of Chianti

9.89.8 out of 10 rating
Exceptional
(26 reviews)
Beautifully restored farmhouse in Greve, heart of Chianti
Greve in Chianti, Chianti
5% off
Price is CA $836
CA $836
CA $6,490 total
CA $6,490 total
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
15% off
Price is CA $221
CA $221
CA $1,778 total
CA $1,778 total
includes taxes & fees
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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)
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)
Traditional Tuscan farmhouse with stunning views
Sleeps 8 · 3 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
97 reviews(97 reviews)
Beautiful house on Chianti hilltop with exceptional views.
Sleeps 8 · 4 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
68 reviews(68 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)
Top rated rentals - Il Cassero
Exceptional stay
1010 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
We spent a week at Valter and his lovely wife's apartment for a week in June/25. It was perfect in every respect. It was the nicest accommodation we have ever had. Valter is a wonderful host. Available when you need him but he respects your privacy. We were welcomed with a beautiful cake and some of his homemade wine(delicious). The apartment was spotless, very well equipped and the pool was a lifesaver when it was so hot. We highly recommend this apartment and would not hesitate to stay there again. Many thanks Valter for a great stay.
Barbara D.
Stayed Jun 2025
Definitely works for me.
1010 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Third time staying.
Grant R.
Stayed May 2025
quick surprise getaway
1010 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
With a last minute decision to surprise a friend for his birthday, this was a perfect place to land. Peaceful, spotless, great location and more than comfortable!
Dana W.
Stayed Sep 2024
Fantastic stay for 4 weeks
1010 out of 10
Exceptionalexceptional
140 reviews(140 reviews)
We spent 4 weeks in this house .The owner was very helpfull the house was top notch If You want to ear the silence it is one of the best place
House was what were expected and more
I recommand this house for people need to relax in peace and calm A special Thanks to the MAMMA
Pierre B.
Stayed Jun 2024
Quiet, Relaxing Villa in a Beautiful Village!
1010 out of 10
Exceptionalexceptional
107 reviews(107 reviews)
When we arrived the owner met us at the appartment and showed us around. His communication with us was great leading upto our arrival.
The setting of this place is absolutely amazing. So quiet and beautiful. The views from both sides of the house are wonderful. We played tennis on the court with such an outstanding view. The pool looks great too, but it was out of season for us.
Well located to visiting various hill top towns. We also did a wine tour at one of the many wineries in the area which I highly recomend (We did Monsanto, but there are lots of options in the area).
The kitchen was very well equiped and everything was in good working order in the house. We cooked here every day. The rooms are large and we were very comfortable for our 5 day stay in April.
It's essential you have a car. If you are looking to get away from the bustle of the city and have a relaxing and quiet setting close to midevil towns and wineries, this place is a terrific option.
Travis P.
Stayed Apr 2024
Great Tuscany Experience
1010 out of 10
Exceptionalexceptional
65 reviews(65 reviews)
Jane and her wonderful husband were so accommodating. They were a wealth of information of places to go & see and where to eat. Their place is in a beautiful location which gives you the true Tuscan experience. Jane arranged for us us to have the most wonderful wine tasting at the Frescobaldi winery. Because Jane knew we were arriving from a long flight from Canada she offered to get us supplies beforehand so that we would have something to eat and not have to go grocery shopping upon arrival. Their home is surrounded by gardens which they grow their own herbs which they told us to help ourselves to.
Everything in their listing was as stated and even more. If we could give more than a five star rating we would.
When we visit Tuscany again we will definitely stay here again.
Thank you so much for making our Tuscany experience one of the best.
Don & Carol Axent
Carol A.
Stayed Sep 2023
2 weeks in Paradise
1010 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
We were a group of 12 family members in an age range from 1 to 71… We were all in heaven for the 14 days of our stay.
The villa is simply magnificent and the pictures posted don’t do justice to the reality of the place. We were all able to have private moments or be all together without feeling that there was a lack of privacy…
We all enjoyed immensely this villa. My older grandsons could play soccer in the park as much as they wanted while the 3 year old could try to play with the ball. As for the 1 year old, she was able to see her brother and cousins playing together in a safe way !
Andrea was an extremely attentive host always able to answer all our questions and arrange for reservations for dinner at a restaurant or to visit local winery. He was always very discreet and would come on a daily basis to make sure that everything was going well. He was never intrusive and always respectful of us.
If you rent this villa, make sure to reserve in advance for the wonderful meals that are catered by Andrea and his lovely wife, Francesca. We had them for 3 nights and we enjoyed 3 very different menus…they were all so extremely good and well prepared. When they leave, the kitchen is immaculate !
The villa is extremely clean and lovingly tended…you can feel that a lot of love went into its changes over the years. All the beds are extremely confortable and the linens and towels are very high quality as well ! If you need anything, you can always ask Andrea.
I wish to be back!
Suzanne H.
Stayed Jul 2023
Beautiful Apartment, Great Location
1010 out of 10
Exceptionalexceptional
71 reviews(71 reviews)
This lovely well-appointed apartment is in a great location - short walks to Campo and Duomo, but on a quiet part of a main street. Our host left a very detailed booklet with wonderful suggestions for first-time visitors to Siena. This included some exellent places to eat just steps from the door. The hosts were always very resposive to our messages, which helped us enjoy the city. We would not hesitate to return to this property.
Alan M.
Stayed May 2023
- 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, yards and more
- More for lessMore space, more privacy, more amenities — more value