
Holiday rentals near Castello di Monsanto
We found 6,377 holiday rentals — enter your dates for availability
Choose the perfect holiday rental within close proximity to Castello di Monsanto. Holiday rentals provide the amenities that you need and want for your stay with friends, family or just your pet, such as a hot tub and garden. 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 - Castello di Monsanto
Showing deals for:3 Oct - 10 Oct
Image gallery for traditional Tuscan Villa, the perfect retreat for families and friends

9.69.6 out of 10 rating
Exceptional
(10 reviews)
traditional Tuscan Villa, the perfect retreat for families and friends
Gambassi Terme, Tuscany
5% off
Price is AU$12,767
AU$12,767
AU$1,824 per night
includes taxes & fees
Image gallery for Villa in the Heart of Chianti

1010 out of 10 rating
Exceptional
(35 reviews)
Villa in the Heart of Chianti
Greve in Chianti, Tuscany
14% off
Price is AU$6,726
AU$6,726
AU$961 per night
includes taxes & fees
Image gallery for Splendid Chianti Tuscany Villa with Panoramic Pool ,Cypress Trees-Lined Drive

9.89.8 out of 10 rating
Exceptional
(6 reviews)
Splendid Chianti Tuscany Villa with Panoramic Pool ,Cypress Trees-Lined Drive
Montespertoli, Città Metropolitana di Firenze
9% off
Price is AU$8,693
AU$8,693
AU$1,242 per night
includes taxes & fees
Image gallery for Beautifully restored farmhouse in the heart of the Chianti

1010 out of 10 rating
Exceptional
(25 reviews)
Beautifully restored farmhouse in the heart of the Chianti
Greve in Chianti, Chianti
5% off
Price is AU$7,181
AU$7,181
AU$1,026 per night
includes taxes & fees
Image gallery for Il Bracconiere, luxury in Chianti - Wifi, swimming pool, parking

8.48.4 out of 10 rating
Very good
(6 reviews)
Il Bracconiere, luxury in Chianti - Wifi, swimming pool, parking
Greve in Chianti, Tuscany
8% off
Price is AU$3,442
AU$3,442
AU$492 per night
includes taxes & fees
Image gallery for Small house with panoramic swimming pool, terrace and wi fi

1010 out of 10 rating
Exceptional
(5 reviews)
Small house with panoramic swimming pool, terrace and wi fi
Casole d'Elsa, Toscana
8% off
Price is AU$1,710
AU$1,710
AU$244 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$2,952
AU$2,952
AU$422 per night
includes taxes & fees
Image gallery for FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops

9.69.6 out of 10 rating
Exceptional
(17 reviews)
FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops
Poggibonsi, Tuscany
8% off
Price is AU$1,585
AU$1,585
AU$226 per night
includes taxes & fees
Image gallery for Exclusive and private Bio Farmhouse in the tuscani countryside

9.89.8 out of 10 rating
Exceptional
(9 reviews)
Exclusive and private Bio Farmhouse in the tuscani countryside
Castelnuovo di Val di Cecina
9% off
Price is AU$3,840
AU$3,840
AU$549 per night
includes taxes & fees
Image gallery for Charming ancient farm house in Chianti

9.69.6 out of 10 rating
Exceptional
(43 reviews)
Charming ancient farm house in Chianti
Montespertoli, Toscana
9% off
Price is AU$4,917
AU$4,917
AU$702 per night
includes taxes & fees
Image gallery for Melograno of Casale Refoli rural apartment 4 people

1010 out of 10 rating
Exceptional
(5 reviews)
Melograno of Casale Refoli rural apartment 4 people
Casole d'Elsa, Tuscany
9% off
Price is AU$2,406
AU$2,406
AU$344 per night
includes taxes & fees
Image gallery for Large Private Tuscany Villa Near Florence Pool Fireplace Superb Views Location

9.69.6 out of 10 rating
Exceptional
(18 reviews)
Large Private Tuscany Villa Near Florence Pool Fireplace Superb Views Location
San Casciano in Val di Pesa, Toscana
8% off
Price is AU$11,647
AU$11,647
AU$1,664 per night
includes taxes & fees
Image gallery for Cottage Gelsomino near Fiorenze, San Gimignano, Siena...

9.09.0 out of 10 rating
Wonderful
(15 reviews)
Cottage Gelsomino near Fiorenze, San Gimignano, Siena...
Gambassi Terme, Tuscany
9% off
Price is AU$1,460
AU$1,460
AU$209 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
(71 reviews)
House in a typical village in the heart of Chianti
Castellina in Chianti, Tuscany
9% off
Price is AU$1,679
AU$1,679
AU$240 per night
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
5% off
Price is AU$12,890
AU$12,890
AU$1,841 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
(14 reviews)
RONDINE: Peaceful farmhouse close to Tuscany 's treasures, 1mile from shops far
Poggibonsi, Tuscany
7% off
Price is AU$1,495
AU$1,495
AU$214 per night
includes taxes & fees
Image gallery for Sangiovese Country House, apartment with pool in a small village in the hills of Chianti

1010 out of 10 rating
Exceptional
(17 reviews)
Sangiovese Country House, apartment with pool in a small village in the hills of Chianti
Tavarnelle Val di Pesa, Tuscany
6% off
Price is AU$2,374
AU$2,374
AU$339 per night
includes taxes & fees
Image gallery for Breathtaking views of the Chianti hills, Tradition, Sustainability and Design

1010 out of 10 rating
Exceptional
(23 reviews)
Breathtaking views of the Chianti hills, Tradition, Sustainability and Design
Montespertoli
9% off
Price is AU$10,806
AU$10,806
AU$1,544 per night
includes taxes & fees
Image gallery for GUFO: Peaceful apartment close to Tuscany 's best treasures, 1 mile from shops

9.69.6 out of 10 rating
Exceptional
(15 reviews)
GUFO: Peaceful apartment close to Tuscany 's best treasures, 1 mile from shops
Poggibonsi, Tuscany
8% off
Price is AU$1,682
AU$1,682
AU$240 per night
includes taxes & fees
Image gallery for A luxury escape in Chianti, great landscape, stunning views, swimming pool

9.09.0 out of 10 rating
Wonderful
(19 reviews)
A luxury escape in Chianti, great landscape, stunning views, swimming pool
Greve in Chianti, Tuscany
8% off
Price is AU$3,294
AU$3,294
AU$471 per night
includes taxes & fees
Image gallery for Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property

8.48.4 out of 10 rating
Very good
(10 reviews)
Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property
Gaiole in Chianti, Toscana
8% off
Price is AU$1,769
AU$1,769
AU$253 per night
includes taxes & fees
Image gallery for Casa Acacia, an ancient tower nestled in the green hills of San Giminiano

8.88.8 out of 10 rating
Excellent
(5 reviews)
Casa Acacia, an ancient tower nestled in the green hills of San Giminiano
San Gimignano, Toscana
16% off
Price is AU$3,564
AU$3,564
AU$509 per night
includes taxes & fees
Image gallery for Arco al Poggio, Arceno Rentals Club, Spacious Chianti Apt, Pool, Concierge, WiFi

1010 out of 10 rating
Exceptional
(63 reviews)
Arco al Poggio, Arceno Rentals Club, Spacious Chianti Apt, Pool, Concierge, WiFi
Castelnuovo Berardenga, Toscana
14% off
Price is AU$3,787
AU$3,787
AU$541 per night
includes taxes & fees
Image gallery for Il Melarancio Country House

1010 out of 10 rating
Exceptional
(17 reviews)
Il Melarancio Country House
Impruneta, Toscana
9% off
Price is AU$1,887
AU$1,887
AU$270 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Castello di Monsanto
Showing deals for: 30 Sept - 3 OctAncient farm situated in the heart of the Chianti Classico Senese, Pool and View
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
90 reviews(90 reviews)
The current price is AU$951
AU$951
for 3 nights, 1 home
AU$317 per night
includes taxes & fees
CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
Sleeps 4 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
25 reviews(25 reviews)
The current price is AU$1,069
AU$1,069
for 3 nights, 1 room
AU$356 per night
includes taxes & fees
Villa Montespertoli In Castellina in Chianti, Tuscany
Sleeps 12 · 6 bedrooms · 7 bathrooms
9.89.8 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
The current price is AU$2,830
AU$2,830
for 3 nights, 1 villa
AU$943 per night
includes taxes & fees
Villa with large garden in the Chianti hills
Sleeps 5 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
70 reviews(70 reviews)
The current price is AU$653
AU$653
for 3 nights, 1 home
AU$218 per night
includes taxes & fees
classy apartment with WIFi in the historic center of Siena
Sleeps 4 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
The current price is AU$891
AU$891
for 3 nights, 1 apartment
AU$297 per night
includes taxes & fees
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Sleeps 2 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
The current price is AU$638
AU$638
for 3 nights, 1 room
AU$213 per night
includes taxes & fees
Top rated rentals - Castello di Monsanto
Stay in Florence
1010 out of 10
Exceptionalexceptional
172 reviews(172 reviews)
The host was very helpful and the location of the property was great. The apartment was also great
Sue W.
Stayed May 2025
Gorgeous tuscan villa
1010 out of 10
Exceptionalexceptional
75 reviews(75 reviews)
Amazing villa, great check in process. Rooms gorgeous, living space's very comfortable. We stayed with 2 families over Christmas, very cosy. A car is very useful to see neighbouring towns.
Yolanda C.
Stayed Dec 2024
Fantastic property
1010 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
The property itself was clean, well equipped & the amenities were great. The pool was exceptional & clean. The surrounding garden was immaculate, spacious & included a bbq which we used. A car is a must to explore beautiful Tuscany. The parents of the host live at the back of the property and they were extremely friendly & helpful. A big thank you to Paola & Giancarlo for making our stay extra special. I would definitely recommend this property.
Ange C.
Stayed Aug 2024
Beautiful farmhouse in Chianti
1010 out of 10
Exceptionalexceptional
138 reviews(138 reviews)
We had a great time staying at Castellina in Chianti. The farmhouse is well equipped, comfortable and a wonderful base to explore Tuscany. The sunsets and views were amazing. We hope to come back some day!
Lauren M.
Stayed Sept 2023
Lovely apartment
1010 out of 10
Exceptionalexceptional
94 reviews(94 reviews)
We enjoyed our stay at Antonella's apartment. It's located in a very convenient area of Florence and easy walking distance to the centre of the city and its location close by to the Boboli gardens. The apartment had everything we needed for our short stay in Florence including a supermarket a few doors down from the apartment and other surrounding shops and restaurants. On our arrival we were warmly welcomed by Antonella's assistant who helped us settle in. We highly recommend Antonella's apartment as being a great introduction to the city of Florence.
Christine R.
Stayed July 2023
Perfect apartment, location and host!
1010 out of 10
Exceptionalexceptional
84 reviews(84 reviews)
I can’t rate this apartment and host highly enough! I rented this because I needed a piano to practice during my stay, but it was all perfect! George (host) communicated with me before, sending me information about things to do while I was in Florence. My train was delayed and so I arrived late but George waited patiently for me to arrive and greeted me with a cool glass of water, showed me around, kindly leaving me with a bottle of vino to kick start my trip. The location was perfect, central to everything you want to see, cafe across the road for morning cappuccino, beautiful restaurant next door and supermarket just down the street. George is a great host, the apartment is stunning and well equipped, I would definitely book this again!
Lian M.
Stayed Aug 2022
A slice of Tuscan heaven
1010 out of 10
Exceptionalexceptional
65 reviews(65 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
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- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value