
Castiglion Fiorentino Station vacation rentals
We found 3,940 vacation rentals — enter your dates for availability
Select the perfect vacation rental that's close to Castiglion Fiorentino Station. Vacation rentals provide the amenities you need and want for your stay with friends, family, or just your pet, such as air conditioning and a pool. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.
Vacation rentals with weekly discounts - Castiglion Fiorentino Station
Showing deals for:Nov 14 - Nov 21
Image gallery for Beautiful Tuscan farmhouse in the countryside with swimming pool

1010 out of 10 rating
Exceptional
(7 reviews)
Beautiful Tuscan farmhouse in the countryside with swimming pool
Cortona, Tuscany
5% off
Price is CA $826
CA $826
CA $6,430 total
CA $6,430 total
includes taxes & fees
Image gallery for Villa & Charme id 1702 , ideal large Families, A/C , large Pool

9.49.4 out of 10 rating
Exceptional
(16 reviews)
Villa & Charme id 1702 , ideal large Families, A/C , large Pool
Castiglione del Lago, Toscana
5% off
Price is CA $917
CA $917
CA $8,189 total
CA $8,189 total
includes taxes & fees
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
10% off
Price is CA $659
CA $659
CA $5,284 total
CA $5,284 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 $875
CA $875
CA $7,150 total
CA $7,150 total
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
10% off
Price is CA $912
CA $912
CA $7,045 total
CA $7,045 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 $1,710
CA $1,710
CA $13,410 total
CA $13,410 total
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
10% off
Price is CA $797
CA $797
CA $6,345 total
CA $6,345 total
includes taxes & fees
Image gallery for Beautiful farmhouse + pool, a glorious setting in hills behind Lake Trasimeno

1010 out of 10 rating
Exceptional
(6 reviews)
Beautiful farmhouse + pool, a glorious setting in hills behind Lake Trasimeno
Lisciano Niccone, Province of Perugia
5% off
Price is CA $417
CA $417
CA $3,240 total
CA $3,240 total
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
10% off
Price is CA $224
CA $224
CA $1,864 total
CA $1,864 total
includes taxes & fees
Image gallery for Scenic Stay in Restored Retreat

1010 out of 10 rating
Exceptional
(5 reviews)
Scenic Stay in Restored Retreat
Monterchi
28% off
Price is CA $156
CA $156
CA $1,448 total
CA $1,448 total
includes taxes & fees
Image gallery for Stunning Villa, gardens, large pool + toddlers pool. In countryside near town.

1010 out of 10 rating
Exceptional
(7 reviews)
Stunning Villa, gardens, large pool + toddlers pool. In countryside near town.
Città di Castello
10% off
Price is CA $505
CA $505
CA $4,006 total
CA $4,006 total
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
15% off
Price is CA $934
CA $934
CA $7,716 total
CA $7,716 total
includes taxes & fees
Image gallery for Villino Cortona - Holiday home with private pool, wifi, a/c - Tuscany

1010 out of 10 rating
Exceptional
(22 reviews)
Villino Cortona - Holiday home with private pool, wifi, a/c - Tuscany
Cortona, AR
28% off
Price is CA $151
CA $151
CA $1,410 total
CA $1,410 total
includes taxes & fees
Image gallery for Large Tuscan villa: Pool, fenced garden, A.C. WI.FI family friendlys 14 Guests

1010 out of 10 rating
Exceptional
(15 reviews)
Large Tuscan villa: Pool, fenced garden, A.C. WI.FI family friendlys 14 Guests
Citerna, PG
19% off
Price is CA $417
CA $417
CA $3,333 total
CA $3,333 total
includes taxes & fees
Image gallery for Luxury Historic Tuscan Farmhouse with swimming pool overlooking the Tiber Valley

9.29.2 out of 10 rating
Wonderful
(11 reviews)
Luxury Historic Tuscan Farmhouse with swimming pool overlooking the Tiber Valley
Caprese Michelangelo, Tuscany
50% off
Price is CA $372
CA $372
CA $3,019 total
CA $3,019 total
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
26% off
Price is CA $834
CA $834
CA $7,103 total
CA $7,103 total
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
10% off
Price is CA $230
CA $230
CA $1,770 total
CA $1,770 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 $126
CA $126
CA $1,099 total
CA $1,099 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 $393
CA $393
CA $3,354 total
CA $3,354 total
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
15% off
Price is CA $137
CA $137
CA $1,168 total
CA $1,168 total
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
10% off
Price is CA $579
CA $579
CA $4,448 total
CA $4,448 total
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
8% off
Price is CA $520
CA $520
CA $3,988 total
CA $3,988 total
includes taxes & fees
Image gallery for Lovely Tuscan Villa: Pool,AC WI.FI 14 guests 7 bedrooms 7bath, Families/friends

9.89.8 out of 10 rating
Exceptional
(16 reviews)
Lovely Tuscan Villa: Pool,AC WI.FI 14 guests 7 bedrooms 7bath, Families/friends
Anghiari, Toscana
10% off
Price is CA $434
CA $434
CA $3,524 total
CA $3,524 total
includes taxes & fees
Image gallery for Apartment in Farmhouse

1010 out of 10 rating
Exceptional
(6 reviews)
Apartment in Farmhouse
Montepulciano, Tuscany
10% off
Price is CA $130
CA $130
CA $1,136 total
CA $1,136 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Castiglion Fiorentino Station
Secluded position,villa with private pool,ideal for families, close to Cortona.
Sleeps 15 · 7 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
57 reviews(57 reviews)
Vacation home Volpe by Interhome
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Beautiful farmhouse with pool
Sleeps 4 · 1 bedroom · 1+ bathroom
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Residenza di Lucia in city center with private terrace
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Top rated rentals - Castiglion Fiorentino Station
Outstanding property and such a helpful host!
1010 out of 10
Exceptionalexceptional
100 reviews(100 reviews)
We had a lovely stay at this beautiful and very comfortable property, that had all of the facilities we needed (and more!) given we were traveling with two small children. The pool was so beautiful it was tempting to just spend the whole week there. The host was so helpful, both before and during our stay, always reachable and provided us with great recommendations of things to do/where to go in the area.
Amélie P.
Stayed Jul 2025
Perfect Location in Montepulciano
1010 out of 10
Exceptionalexceptional
49 reviews(49 reviews)
We spent 12 days in Montepulciano on a cycling trip and the location was perfect. Located just a few steps from the main street in the Old City you have quick access to the shops, restaurants, and historic sites - not to mention a spectacular view of the Val D’Orcia valley to the east. Royce (owner) was attentive to all questions and requests.
Paul E.
Stayed Jun 2025
Fantastic time, Central location
1010 out of 10
Exceptionalexceptional
82 reviews(82 reviews)
We were a group of 4 couples and found there was plenty of room for all of us. The property as better in person than we had expected. We had a car so it was really easy to get around and see all the towns nearby. Very beautiful property with great vistas. So relaxing to hang out at the pool or the deck.
Elfrieda S.
Stayed Sep 2024
Incredible Property
1010 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
I cannot rate this property highly enough!
Everything was gorgeous and impeccable. Magnificent views of Cortona and the valley below from the sprawling front lawn and the beautiful pool, a well equipped kitchen, loads of space, beautiful bathrooms and super gracious hosts . Luigi was always available, accommodating and ready to offer suggestions and recommendations for dining, day trips and wineries. This is a beautiful, special place. Thank you for hosting us!
Carol G.
Stayed Jul 2024
Tuscan retreat
1010 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
We had a group of 11 stay and could not have loved our time more. The location was a great central spot to drive to different towns. We loved relaxing by the pools in the afternoons and our dinners al fresco. An incredible place to spend your vacation.
Shannon H.
Stayed Jul 2024
Heart warming hospitality
1010 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Anna Maria & her daughter Lorella met us on arrival. They both were warm & welcoming. They ensured we were very comfortable with the property & surrounding amenities before they left. The property was better than described on VRBO’s site. The charm of the stone farm house can’t be appreciated in pictures. Living the experience is the only way to truly get a feeling of Tuscan living. Although the property was 9 kms from Cortona it was an easy country drive to town. We appreciated leaving the busyness of the surrounding tourist attractions and going back to the quiet farmhouse at the end of the day! Fratticciola is a small community but the local people were accepting & friendly! The hosts were exceptional. Anna Maria’s wine, vin Santa & cantucci was a nice welcoming gift. During our visit she ensured we had everything we needed & dropped off goodies from time to time. Lorella was only a text message away. She was very helpful with information on the surrounding area. This review cannot do justice in describing how exceptional Anna Maria & her family were as hosts. We will return!
Wade B.
Stayed Apr 2024
Perfect stay in a perfect villa with a perfect host.
1010 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
Fabrizio was very welcoming, helpful when needed. The house is simply incredible, well located and well furnished. Awesome view, could not wish for more.
Simon L.
Stayed Sep 2023
Tuscan Villa on the mountain
1010 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
Vacationed in this villa for one week with another family. We were 9 people living in the villa and it was enough space for all! The Villa lies on a mountain making the driving up a bit of a challenge however once you arrived at villa Caprile it is worth it! In addition to its picturesque views, the landscaping was very well maintained, the pool was cleaned every morning, and Denise welcomed us with pleasure. The outside eating area was perfect for the nice breeze. There was fan air conditioning in every room which was a plus. Loved all the accommodations such as the speakers, TV. Very ideal location also!
Joe A.
Stayed Aug 2022
- 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