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

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Our top choices for Cortona vacation homes

1. Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is ¥11,637
¥14,962 total
includes taxes & fees
Sep 18 - Sep 19
Holiday home with panoramic terrace ideal for families and couples

2. Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2 reviews)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is ¥14,593
¥17,918 total
includes taxes & fees
Sep 1 - Sep 2
Montecchio di Cortona

3. Farmhouse with mountain views hot tub

Farmhouse with mountain views hot tub
Cortona
The price is ¥37,683
¥73,282 total
includes taxes & fees
Aug 26 - Aug 27
Farmhouse with mountain views hot tub

4. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
Cortona
The price is ¥48,665
¥56,349 total
includes taxes & fees
Aug 26 - Aug 27
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

5. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is ¥8,312
¥12,376 total
includes taxes & fees
Sep 1 - Sep 2
Happy Nest Tuscany Between Florence and Rome

6. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is ¥14,181
¥19,722 total
includes taxes & fees
Aug 23 - Aug 24
Dolce Casa 2 by Tiny Away

7. Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
The price is ¥13,207
¥26,137 total
includes taxes & fees
Aug 23 - Aug 24
Tolletta 10 e Lode - One Bedroom House, Sleeps 4

8. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is ¥15,277
¥20,818 total
includes taxes & fees
Aug 23 - Aug 24
Dolce Casa 1 by Tiny Away

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

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Foiano della Chiana
The price is ¥14,192
¥14,931 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

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

Double room with private bathroom in the countryside 5 minutes from Montepulciano
Toscana
The price is ¥19,950
¥29,740 total
includes taxes & fees
Aug 22 - Aug 23
Double room with private bathroom in the countryside 5 minutes from Montepulciano

11. Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria

Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria
Lisciano Niccone
The price is ¥648,769
¥649,138 total
includes taxes & fees
Sep 20 - Sep 21
Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria

12. Gorgeously restored tranquil farmhouse

Gorgeously restored tranquil farmhouse
Castiglione Del Lago PG
9.6 out of 10, Exceptional, (5 reviews)
"Nice relaxed location, a generous sized cottage with all the amenities, and excellent feedback from the client if we had queries. A perfect stay"
United Kingdom
Nigel G.
The price is ¥49,501
¥56,603 total
includes taxes & fees
Sep 1 - Sep 2
Gorgeously restored tranquil farmhouse

13. Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is ¥19,506
¥24,308 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Home 'La Casina All'angolo'

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

Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany
Castiglione del Lago
10.0 out of 10, Exceptional, (1 review)
"Great location in beautiful Tuscany. Very nice host and hospitallity. Would come back again!"
United States
Bin L.
The price is ¥18,289
¥26,787 total
includes taxes & fees
Sep 2 - Sep 3
Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany

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

Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi
Monte San Savino
6.0 out of 10, (2 reviews)
"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...
Canada
Anonymous traveler
The price is ¥49,880
¥66,691 total
includes taxes & fees
Sep 11 - Sep 12
Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

16. "Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (11 reviews)
"An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! "
Australia
Dan
The price is ¥18,472
¥22,536 total
includes taxes & fees
Sep 8 - Sep 9
"Il Focolare" Superior Apartment in Monticchiello

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

Charming bungalow with whirlpool in Tuscany: peace, nature and comfort
Antria
The price is ¥24,937
¥29,555 total
includes taxes & fees
Aug 25 - Aug 26
Charming bungalow with whirlpool in Tuscany: peace, nature and comfort

18. Welcome to Villa Dolce Vita - your private paradise in Tuscany

Welcome to Villa Dolce Vita - your private paradise in Tuscany
Pieve Vecchia
8.4 out of 10, Very Good, (6 reviews)
"Perfect for a couple. The villa is beautiful and on large grounds. We used the pool every day. Very close to other towns, restaurants, etc, but a car is recommended. "
Canada
Darren B.
The price is ¥66,507
¥75,559 total
includes taxes & fees
Aug 24 - Aug 25
Welcome to Villa Dolce Vita - your private paradise in Tuscany

19. Apartment "Pugnano Alto - Castagna" with Shared Pool and Wi-Fi

Apartment "Pugnano Alto - Castagna" with Shared Pool and Wi-Fi
Lisciano Niccone
10.0 out of 10, Exceptional, (1 review)
"Pros: The Quietness of the wonderful mornings, in the middle of Tuscan Woods. The clean and big pool with a view. The host, very friendly and engaged. a perfect vacation!"
United States
Anonymous traveler
The price is ¥77,503
¥77,872 total
includes taxes & fees
Sep 4 - Sep 5
Apartment "Pugnano Alto - Castagna" with Shared Pool and Wi-Fi

20. Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3 reviews)
"Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! "
United States
Rob C.
The price is ¥36,574
¥52,090 total
includes taxes & fees
Aug 23 - Aug 24
Eagle House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cortona Hotel Reviews

Find out more about Cortona

Cortona Vacation Homes information

Number of reviews
26
Accommodation
221 Vacation Homes
Lowest Price
¥12,376
Highest Price
¥649,138