Cortona Vacation Homes

A hillside town with historic buildings, a church, and vineyards.

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Our top choices for Cortona holiday homes

Holiday home with panoramic terrace ideal for families and couples

Cortona

HK$722 total

includes taxes & fees

27 Jul - 28 Jul

Montecchio di Cortona

Montecchio

Monica S.

HK$910 total

includes taxes & fees

27 Jul - 28 Jul

Apartment "Papà Giuseppe Il Fienile" with Shared Pool and Wi-Fi

Cortona

Farmhouse with mountain views hot tub

Cortona

HK$3,538 total

includes taxes & fees

2 Aug - 3 Aug

Apartment "Papà Giuseppe La Colombaia" with Shared Pool and Wi-Fi

Cortona

Amanda C.

HK$1,435 total

includes taxes & fees

28 Jul - 29 Jul

Happy Nest Tuscany Between Florence and Rome

Castiglion Fiorentino

HK$918 total

includes taxes & fees

27 Jul - 28 Jul

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

Foiano della Chiana

HK$721 total

includes taxes & fees

27 Jul - 28 Jul

Dolce Casa 2 by Tiny Away

Rigutino

HK$952 total

includes taxes & fees

27 Jul - 28 Jul

Dolce Casa 1 by Tiny Away

Rigutino

HK$1,007 total

includes taxes & fees

27 Jul - 28 Jul

Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Arezzo Centro Storico

Maria Gemma

HK$1,262 total

includes taxes & fees

9 Aug - 10 Aug

Double room with private bathroom in the countryside 5 minutes from Montepulciano

Toscana

HK$1,436 total

includes taxes & fees

27 Jul - 28 Jul

mini house with park, in the province of Siena, btw Valdichiana and Val d'Orcia

Sinalunga

Robert R.

Poggio del Sole

Castiglione del Lago

RAUL

HK$2,526 total

includes taxes & fees

29 Jul - 30 Jul

Gorgeously restored tranquil farmhouse

Castiglione Del Lago PG

John C.

HK$2,989 total

includes taxes & fees

28 Jul - 29 Jul

Holiday Home 'La Casina All'angolo'

Civitella in Val di Chiana

Charming bungalow with whirlpool in Tuscany: peace, nature and comfort

Antria

HK$1,436 total

includes taxes & fees

27 Jul - 28 Jul

Holiday Home in Villa Pandolfina near Montepulciano

Acquaviva

HK$2,301 total

includes taxes & fees

2 Aug - 3 Aug

Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

Monte San Savino

"My husband and I booked this place and were unable to stay due to lack of communication regarding check-in procedure. The listing states the host will make contact 3 days before which didn’t happen. We sent several messages the day of check-in and didn’t hear from the host until well after the check-in time (4pm). Given the remote location and time of day, we were worried we wouldn’t have anywhere to stay for the night so we booked a hotel in Arezzo which we were lucky to get on a holiday...

Anonymous traveller

HK$2,015 total

includes taxes & fees

31 Jul - 1 Aug

Romantic farm in the Sienese hills

Trequanda, Siena

"Zum positiven: Kommunikation mit dem Gastgeber war sehr gut und informativ. Check in war gut, Antonio der die Übergabe der Schlüssel und die Erläuterung zum Appartement machte sprach leider nur italienisch, aber er war sehr freundlich und mit Händen und Füßen funktionierte es gut. Das Apartment war wirklich sehr schön und mit Liebe zum Detail eingerichtet. Die Location war wirklich sehr schön.Nun zum negativen: An allen Fenstern der Unterkunft waren keine Fliegengitter angebracht was es...

Harald B.

HK$1,775 total

includes taxes & fees

6 Aug - 7 Aug

Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany

Castiglione del Lago

HK$1,534 total

includes taxes & fees

27 Jul - 28 Jul

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Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Beautiful oasis in a beautiful town"

"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona

10/10 Excellent

"Lovely villa in great location. Bedrooms were all good size, good kitchen and indoor/outdoor eating areas. Excellent air conditioning. Beautiful grounds with olive trees and lovely pool area. Beautiful view of Cortona."

A small cottage in authentic Tuscany. Serves 4

10/10 Excellent

"We absolutely loved our stay at Anna Maria's property in Fratticciola. The bedrooms are roomy, warmly decorated. We had fun cooking in the galley kitchen--the cooktop range was easy to operate and included a small burner just for the mocha. We didn't use the oven, but one is available. There are plenty of plates, bowls, silverware along with a few cooking supplies including their own delicious olive oil. Our stay was also greeted with some delicious homemade Cantucci and vin santo, a plate of bruschetta, and Panzanella. The futon in the living/dining area is just enough comfort but does seat low to the ground. The cottage has a wonderful homey feeling and is slightly tucked away from the road with small inviting gardens for lounging, reading, or sipping espresso. There is also a table and chairs for outdoor dining below the stairs. If you do not want to sit in the garden, a small table with two chairs are folded at the top of the stairs on the platform. Casa di Bini is a rustic, charming place with its own sense of home and romance. The surrounding area is gorgeous, quiet, and you are short drives from many beautiful places. Highly recommended!"

Cortona Resort Spa

10/10 Excellent

"Pro: gorgeous and spacious property, we were upgraded to a junior suite that was lovely, attentive staff, and incredible amenities. Pool was wonderful for tired bodies. Con: very few. The restaurant on site has pretty limited menu, toilet in room kept running all night long- informed staff on checkout (as it was troublesome to flush, and wasting water), fridge in room- housed in a cabinet that I feel caused it to overheat… and therefore was not very powerful enough to keep drinks cold. Loved this place and the attentive staff. Super friendly and wonderful hospitality."

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