Holiday Homes in Cortona

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Check prices for these dates

Next weekend
9 Jan - 11 Jan
In two weeks
16 Jan - 18 Jan
In one month
30 Jan - 1 Feb
In two months
27 Feb - 1 Mar

Our top choices for Cortona holiday homes

Property grounds
Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is NZ$186
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday home with panoramic terrace ideal for families and couples
Fridge, stovetop, electric kettle, cookware/dishes/utensils
Apartment "Papà Giuseppe La Colombaia" with Shared Pool & Wi-Fi

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

Apartment "Papà Giuseppe La Colombaia" with Shared Pool & Wi-Fi
Cortona
10.0 out of 10, Exceptional, (1)
"Pros: Es war ganz toll. Das Klima mit 34 Grad sehr heiß aber durch den Pool geht auch das sehr gut. Der Gastgeber ist super freundlich... wir sprechen null italienisch aber das war nur ein kleines Hinderniss."
Germany
Anonymous traveller
The price is NZ$253
includes taxes & fees
8 Jan - 9 Jan 2026
Apartment "Papà Giuseppe La Colombaia" with Shared Pool & Wi-Fi
Dining
Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi
Cortona
9.0 out of 10, Wonderful, (2)
"Pros: Il camino è stato come tornare bambini.Atmosfera Natalizia e tanto di più. Cons: Il Bidè non funzionava."
Italy
Anonymous traveller
The price is NZ$204
includes taxes & fees
5 Jan - 6 Jan 2026
Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi
Smart TV, books, computer monitors
Netik Apartment Cortona- Garden & Vineyard in Tuscany

Netik Apartment Cortona- Garden & Vineyard in Tuscany

Netik Apartment Cortona- Garden & Vineyard in Tuscany
Vallone Pip
The price is NZ$207
includes taxes & fees
7 Jan - 8 Jan 2026
Netik Apartment Cortona- Garden & Vineyard in Tuscany
1 bedroom, iron/ironing board, free WiFi, bed sheets
House in the Cortona countryside

House in the Cortona countryside

House in the Cortona countryside
Fratticciola
10.0 out of 10, Exceptional, (1)
"Host was extremely welcoming. Met us when we arrived and explained usage of all the amenities, including the clothes washer. Cottage was quintessential Rural Italian home. The hostess even provided us with some local wine and homemade biscotti. "
United States
Nancy F.
The price is NZ$219
includes taxes & fees
1 Jan - 2 Jan 2026
House in the Cortona countryside
Exterior
Montecchio di Cortona

Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
Montecchio di Cortona
Property grounds
Apartment "La Vecchia Fornace Casa Gialla" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace Casa Gialla" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace Casa Gialla" with Shared Pool & Wi-Fi
Cortona
The price is NZ$212
includes taxes & fees
17 Jan - 18 Jan 2026
Apartment "La Vecchia Fornace Casa Gialla" with Shared Pool & Wi-Fi
Fridge, oven, stovetop, dishwasher
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Cortona
8.0 out of 10, Very good, (1)
"Pros: Authentiek Toscaanse boerderij ( wij hadden de bovenste etage) met prachtige tuin en lekker zwembad met mooi uitzicht. De gastheer Angelo was top en de Toscaanse diners waren onvergetelijk. Bedankt dat ik mijn verjaardag zo heb mogen vieren. Hele mooie herinnering. Pizza’s bakken was ook een feest. Ook heel fijn dat er een airco was. Onze 4 puber jongens hebben zich prima vermaakt en leuk dat er nog andere gasten zijn uit andere appartementen die je dan ziet op hetToscaanse diner. Top...
Netherlands
Anonymous traveller
The price is NZ$231
includes taxes & fees
1 Jan - 2 Jan 2026
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Exterior
Apartment "La Vecchia Fornace Casa Rossa" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace Casa Rossa" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace Casa Rossa" with Shared Pool & Wi-Fi
Cortona
The price is NZ$253
includes taxes & fees
1 Jan - 2 Jan 2026
Apartment "La Vecchia Fornace Casa Rossa" with Shared Pool & Wi-Fi
Interior entrance
Poggio del Sole

Poggio del Sole

Poggio del Sole
Castiglione del Lago
8.0 out of 10, Very good, (4)
"El hotel no alcanzó el agua caliente y no se pudo bañar parte de la familia no contaba con suficientes amenidades "
Mexico
RAUL
Poggio del Sole
Property grounds
LANDLORD ALBACHIARA

LANDLORD ALBACHIARA

LANDLORD ALBACHIARA
Ramazzano - Le Pulci
10.0 out of 10, Exceptional, (1)
"Ottimo appartamento, molto pulito e confortevole"
Italy
Fabio
The price is NZ$274
includes taxes & fees
1 Jan - 2 Jan 2026
LANDLORD ALBACHIARA
Interior
Holiday Home "Palazzetto Bovini" with Wi-Fi and Private Pool

Holiday Home "Palazzetto Bovini" with Wi-Fi and Private Pool

Holiday Home "Palazzetto Bovini" with Wi-Fi and Private Pool
perugia
10.0 out of 10, Exceptional, (1)
"Pros: Great hosts, who were super helpful and responsive. Beautiful house and gardens. Cons: Nothing - it was great!"
United States
Anonymous traveller
The price is NZ$6,180
includes taxes & fees
7 Jan - 8 Jan 2026
Holiday Home "Palazzetto Bovini" with Wi-Fi and Private Pool
1 bedroom, iron/ironing board, free WiFi, bed sheets
Tolletta 10 e Lode - One Bedroom House, Sleeps 4

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)
" 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 NZ$309
includes taxes & fees
12 Jan - 13 Jan 2026
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Pool
Eagle House

Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3)
"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 NZ$699
includes taxes & fees
1 Jan - 2 Jan 2026
Eagle House
Property grounds
Dolce Casa 2 Summary:

Dolce Casa 2 Summary:

Dolce Casa 2 Summary:
Arezzo
The price is NZ$226
includes taxes & fees
8 Jan - 9 Jan 2026
Dolce Casa 2 Summary:
Exterior detail
Independent house in the historic center

Independent house in the historic center

Independent house in the historic center
CASTIGLIONE D'ORCIA
9.4 out of 10, Exceptional, (9)
"Stayed here during the Tuscany Trail and was perfect for 4 of us. Centre of town and a great restaurant recommendation too! "
United Kingdom
Graham S.
The price is NZ$341
includes taxes & fees
2 Jan - 3 Jan 2026
Independent house in the historic center
Outdoor dining
Ermione seen on the Val d'Orcia

Ermione seen on the Val d'Orcia

Ermione seen on the Val d'Orcia
Castiglione d'Orcia
8.8 out of 10, Excellent, (3)
"Alles top"
Germany
ANDREAS ALEXANDER
The price is NZ$354
includes taxes & fees
11 Jan - 12 Jan 2026
Ermione seen on the Val d'Orcia
Comfort Apartment, 3 Bedrooms | View from property
Rustic Holiday Home in Citta di Castello With Swimming Pool

Rustic Holiday Home in Citta di Castello With Swimming Pool

Rustic Holiday Home in Citta di Castello With Swimming Pool
Città di Castello
The price is NZ$284
includes taxes & fees
10 Jan - 11 Jan 2026
Rustic Holiday Home in Citta di Castello With Swimming Pool
Outdoor dining
Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!

Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!

Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!
Castel Rigone
10.0 out of 10, Exceptional, (3)
"The only thing this place could have that it doesn't is an infinity pool! We loved it here. It was a last minute booking and the host was super helpful. STUNNING views from the patio, and the lake is a short drive down the hill. Also, a very cool little town with restaurants just a two minute drive.Our favorite stays in Italy we're in these little remote towns. Soooo nice. "
United States
Adam H.
The price is NZ$227
includes taxes & fees
11 Jan - 12 Jan 2026
Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!
Interior
"Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (8)
"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 NZ$247
includes taxes & fees
5 Jan - 6 Jan 2026
"Il Focolare" Superior Apartment in Monticchiello
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Everything was perfect! Would like to give this Property a 6 Star rating. The staff made you feel like royalty!!"
Sabrina 4-night trip
Posted 12 days ago
Monastero di Cortona Hotel & Spa

Find out more about Cortona

Cortona Holiday Homes information

Number of reviews
27
Accommodation
222 Holiday Homes
Lowest Price
NZ$186
Highest Price
NZ$6,180

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