
Holiday rentals near Castellina Fortress
We found 1,460 holiday rentals — enter your dates for availability
Choose the perfect holiday rental within close proximity to Castellina Fortress. Holiday rentals offer the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Castellina Fortress
Showing deals for:5 Dec - 12 Dec
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$4,078
AU$4,078
for 7 nights, 1 villa
AU$583 per night
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
9% off
Price is AU$16,870
AU$16,870
for 7 nights, 1 villa
AU$2,410 per night
includes taxes & fees
Image gallery for Beautifully restored farmhouse in Greve, heart of Chianti

9.89.8 out of 10 rating
Exceptional
(28 reviews)
Beautifully restored farmhouse in Greve, heart of Chianti
Greve in Chianti, Chianti
5% off
Price is AU$7,190
AU$7,190
for 7 nights, 1 room
AU$1,027 per night
includes taxes & fees
Image gallery for BEAUTIFUL VILLA with private Pool in the heart of Chianti

1010 out of 10 rating
Exceptional
(26 reviews)
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Castelnuovo Berardenga
6% off
Price is AU$11,365
AU$11,365
for 7 nights, 1 villa
AU$1,624 per night
includes taxes & fees
Image gallery for FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops

9.49.4 out of 10 rating
Exceptional
(18 reviews)
FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops
Poggibonsi, Tuscany
8% off
Price is AU$1,932
AU$1,932
for 7 nights, 1 cottage
AU$276 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$2,955
AU$2,955
for 7 nights, 1 villa
AU$422 per night
includes taxes & fees
Image gallery for House in a typical village in the heart of Chianti

9.69.6 out of 10 rating
Exceptional
(73 reviews)
House in a typical village in the heart of Chianti
Castellina in Chianti, Tuscany
9% off
Price is AU$1,148
AU$1,148
for 7 nights, 1 home
AU$164 per night
includes taxes & fees
Image gallery for Farmhouse 15th century in Chianti with private garden and lake

1010 out of 10 rating
Exceptional
(13 reviews)
Farmhouse 15th century in Chianti with private garden and lake
Radda in Chianti, Tuscany
8% off
Price is AU$2,062
AU$2,062
for 7 nights, 1 room
AU$295 per night
includes taxes & fees
Image gallery for RONDINE: Peaceful farmhouse close to Tuscany 's treasures, 1mile from shops far

1010 out of 10 rating
Exceptional
(15 reviews)
RONDINE: Peaceful farmhouse close to Tuscany 's treasures, 1mile from shops far
Poggibonsi, Tuscany
8% off
Price is AU$1,647
AU$1,647
for 7 nights, 1 apartment
AU$235 per night
includes taxes & fees
Image gallery for GUFO: Peaceful apartment close to Tuscany 's best treasures, 1 mile from shops

9.49.4 out of 10 rating
Exceptional
(16 reviews)
GUFO: Peaceful apartment close to Tuscany 's best treasures, 1 mile from shops
Poggibonsi, Tuscany
8% off
Price is AU$1,647
AU$1,647
for 7 nights, 1 apartment
AU$235 per night
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
9% off
Price is AU$2,271
AU$2,271
for 7 nights, 1 home
AU$324 per night
includes taxes & fees
Image gallery for Ancient stone farmhouse on a top of Chianti Hill with private garden and lake

9.69.6 out of 10 rating
Exceptional
(5 reviews)
Ancient stone farmhouse on a top of Chianti Hill with private garden and lake
Radda in Chianti, Tuscany
8% off
Price is AU$1,575
AU$1,575
for 7 nights, 1 room
AU$225 per night
includes taxes & fees
Image gallery for Ancient house in Chianti Hills with private lake and garden

1010 out of 10 rating
Exceptional
(5 reviews)
Ancient house in Chianti Hills with private lake and garden
Radda in Chianti, Tuscany
8% off
Price is AU$1,739
AU$1,739
for 7 nights, 1 room
AU$248 per night
includes taxes & fees
Image gallery for "TERRACE BELL"

1010 out of 10 rating
Exceptional
(27 reviews)
"TERRACE BELL"
Greve in Chianti, Tuscany
9% off
Price is AU$1,454
AU$1,454
for 7 nights, 1 apartment
AU$208 per night
includes taxes & fees
Image gallery for Casa Grazia, quiet nest near the center. free parking all over the street.

1010 out of 10 rating
Exceptional
(11 reviews)
Casa Grazia, quiet nest near the center. free parking all over the street.
Greve in Chianti, Toscana
10% off
Price is AU$1,278
AU$1,278
for 7 nights, 1 apartment
AU$183 per night
includes taxes & fees
Image gallery for Stone Farmhouse in Chianti Hill between Florence, Siena private veranda and lake

1010 out of 10 rating
Exceptional
(34 reviews)
Stone Farmhouse in Chianti Hill between Florence, Siena private veranda and lake
Radda in Chianti, Tuscany
8% off
Price is AU$2,258
AU$2,258
for 7 nights, 1 room
AU$323 per night
includes taxes & fees
Image gallery for 15th century barn fully renovated in a stylish style with gorgeous swimming pool

9.29.2 out of 10 rating
Wonderful
(10 reviews)
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Monteriggioni, Provincia di Siena
9% off
Price is AU$8,846
AU$8,846
for 7 nights, 1 villa
AU$1,264 per night
includes taxes & fees
Image gallery for PETIROSSO: Peaceful apt close to Tuscany 's best treasures, 1 mile from shops

9.09.0 out of 10 rating
Wonderful
(10 reviews)
PETIROSSO: Peaceful apt close to Tuscany 's best treasures, 1 mile from shops
Poggibonsi, Tuscany
8% off
Price is AU$1,707
AU$1,707
for 7 nights, 1 apartment
AU$244 per night
includes taxes & fees
Image gallery for PASSERO:Peaceful farmhouse close to Tuscany 's best treasures, 1 mile from shops

9.29.2 out of 10 rating
Wonderful
(20 reviews)
PASSERO:Peaceful farmhouse close to Tuscany 's best treasures, 1 mile from shops
Poggibonsi, Tuscany
7% off
Price is AU$2,317
AU$2,317
for 7 nights, 1 apartment
AU$331 per night
includes taxes & fees
Image gallery for The Photographer's House

1010 out of 10 rating
Exceptional
(11 reviews)
The Photographer's House
Colle di Val d'Elsa, Toscana
14% off
Price is AU$1,175
AU$1,175
for 7 nights, 1 home
AU$168 per night
includes taxes & fees
Image gallery for Villa il Castellaccio #1 Chianti, Tuscany apartment with swimming pools

1010 out of 10 rating
Exceptional
(14 reviews)
Villa il Castellaccio #1 Chianti, Tuscany apartment with swimming pools
Greve in Chianti, Toscana
11% off
Price is AU$1,630
AU$1,630
for 7 nights, 1 apartment
AU$233 per night
includes taxes & fees
Image gallery for Chianti: farm 4 forest with swimming pool

8.88.8 out of 10 rating
Excellent
(6 reviews)
Chianti: farm 4 forest with swimming pool
Castellina in Chianti, Toscana
11% off
Price is AU$1,574
AU$1,574
for 7 nights, 1 room
AU$225 per night
includes taxes & fees
Image gallery for PRIVATE VILLA IN THE HEART OF CHIANTI with pools and stunning views

1010 out of 10 rating
Exceptional
(40 reviews)
PRIVATE VILLA IN THE HEART OF CHIANTI with pools and stunning views
Castelnuovo Berardenga, Tuscany
9% off
Price is AU$9,110
AU$9,110
for 7 nights, 1 villa
AU$1,301 per night
includes taxes & fees
Image gallery for Farmhouse in old mill nestled in the beautiful Chianti hills

8.68.6 out of 10 rating
Excellent
(17 reviews)
Farmhouse in old mill nestled in the beautiful Chianti hills
Monteriggioni, Toscana
5% off
Price is AU$1,681
AU$1,681
for 7 nights, 1 home
AU$240 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Castellina Fortress
Authentic Stone House with Pool & Scenic Views – Perfect for Nature Lovers
Sleeps 6 · 3 bedrooms · 2+ bathrooms
SPECIAL PRIVE !! Exclusive Villa with Pool near San Gimignano + FREE WIFI
Sleeps 18 · 8 bedrooms · 9 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Carraretto In Castellina in Chianti, Tuscany
Sleeps 6 · 3 bedrooms · 2 bathrooms
8.08.0 out of 10
Very goodvery good
1 review(1 review)
Beautiful house on Chianti hilltop with exceptional views.
Sleeps 8 · 4 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
68 reviews(68 reviews)
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Sleeps 8 · 4 bedrooms · 3 bathrooms
8.08.0 out of 10
Very goodvery good
1 review(1 review)
Chianti House
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Top rated rentals - Castellina Fortress
Amazing
1010 out of 10
Exceptionalexceptional
140 reviews(140 reviews)
We loved our stay! The Farmhouse is really lovely and the view out the back is exceptional. We enjoyed a lot of home cooked meals with the most stunning view. Daniele was amazing to communicate with as well. Definitely hope to be back one day!
Rebekah T.
Stayed July 2025
A very special experience
1010 out of 10
Exceptionalexceptional
44 reviews(44 reviews)
We loved our time here. Views were amazing, house comfortable and close to beautiful towns. You need a car to experience the most amazing food and scenery A very memorable holiday indeed
Marietta R.
Stayed May 2025
Relaxing and scenic authentic Chianti experience
1010 out of 10
Exceptionalexceptional
91 reviews(91 reviews)
This is one of those conflicted reviews. I’d like to keep Le Bagnaie secret so we can book in future but I can’t resist posting about the experience. I can’t fault anything about the stay. The check in instructions were easy, property is well appointed and spotless, spectacular views, great pool and beautiful district. We drove around the surrounding towns and wineries. The meal from Serena was a real highlight. We didn’t want to leave
Damian H.
Stayed Sept 2024
A true Tuscan Villa
1010 out of 10
Exceptionalexceptional
20 reviews(20 reviews)
The property views are even better in real life. The villa, grounds and pool are well looked after. Amazing stay.
Just a note for those that may need to know…all the bedrooms are upstairs. There is one bathroom downstairs and 2 upstairs.
Alessio was a fantastic host.
We loved our stay! Thank you
Michelle L.
Stayed June 2024
A little life in Chianti
1010 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
Our stay was a delight. The apartment is in a great location for easy access to restaurants, shops, car parking and facilities. We used it as a base to tour around Chianti. Cara, the owner, is very responsive and friendly. Carlotta welcomed us to Greve and was a great source of local information.
Maria & Peter C.
Stayed Apr 2023
A slice of Tuscan heaven
1010 out of 10
Exceptionalexceptional
68 reviews(68 reviews)
My family, including my parents and children, spent the most wonderful week at this beautiful property! The house and private outdoor terrace is huge, with lots of different spaces to spend eating and drinking and relaxing. The pool was incredible - the kids loved the diving board and making friends with other children who were also staying in the hamlet.
It was the perfect house for us to spend a week relaxing in Tuscany!
Amanda O.
Stayed Aug 2019
Fantastic location right in the heart of chianti
1010 out of 10
Exceptionalexceptional
66 reviews(66 reviews)
I stayed here during april, when the weather can be cold and can Ben marvelous, not matter what the weather is doing Tuscany and chianti are always beautiful. This was our home base for trips to Florence, montepulciano and other short drives around the chianti region. Rada was my personal favorite, exactly what I was looking for in a Tuscan holiday. Lis was wonderful, accommodating and extremely friendly, I could not recommend this property for a chianti stay more !
Nicholas M.
Stayed Apr 2017
- 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