Pozzo Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Pozzo vacation rentals

Exterior
Il Poggio dell'Eremita

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (59)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is ￥27,304
￥31,168 total
includes taxes & fees
Dec 30 - Dec 31
Il Poggio dell'Eremita
Premium bedding, down comforters, minibar, in-room safe
La Locanda di San Francesco

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (131)
"Great room-great staff-great location"
United States
Richard
The price is ￥27,062
￥30,505 total
includes taxes & fees
Jan 18 - Jan 19, 2026
La Locanda di San Francesco
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 ￥12,878
￥16,926 total
includes taxes & fees
Dec 28 - Dec 29
Holiday home with panoramic terrace ideal for families and couples
Dining
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Monteaperti
10.0 out of 10, Exceptional, (2)
"We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite"
United States
Ian F.
The price is ￥26,492
￥30,908 total
includes taxes & fees
Dec 28 - Dec 29
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
1 bedroom, desk, iron/ironing board, WiFi
Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Shabby Chic House<br>(Independent & balcony)
Cortona Old Town
10.0 out of 10, Exceptional, (3)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
The price is ￥17,386
￥21,250 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Cortona Shabby Chic House<br>(Independent & balcony)
Exterior
The house in the village - Angelica apartment - Vald'Orcia

The house in the village - Angelica apartment - Vald'Orcia

The house in the village - Angelica apartment - Vald'Orcia
Monticchiello
10.0 out of 10, Exceptional, (11)
"Nice and comfortable house in a beautiful tiny village "
United States
Lana A.
The price is ￥17,386
￥21,066 total
includes taxes & fees
Jan 8 - Jan 9, 2026
The house in the village - Angelica apartment - Vald'Orcia
Property grounds
L'OLIVO Tourist Apartment CIN IT051021C2MW8M4HLF

L'OLIVO Tourist Apartment CIN IT051021C2MW8M4HLF

L'OLIVO Tourist Apartment CIN IT051021C2MW8M4HLF
Lucignano
10.0 out of 10, Exceptional, (1)
"Auch wenn der Vermieter nicht wirklich englisch spricht, war der check-in völlig problemlos, Kontakt ständig möglich, wertvolle Tipps zur Umgebung erhältlich. Ein herzensguter Vermieter, der uns sogar das Geld zurück gab für den einen Tag der früheren Abreise, die private Gründe hatte. Kleiner Mangel : im 2. Schlafraum kein Insektenschutz und Autobahn ist bei ungüstigem Wind zu hören. Aber das ist Jammer auf hohem Niveau. Wir hatten einen sehr schönen Urlaub und haben uns ins Städtchen verliebt!...
Germany
Ilka R.
The price is ￥29,436
￥33,116 total
includes taxes & fees
Dec 28 - Dec 29
L'OLIVO Tourist Apartment CIN IT051021C2MW8M4HLF
Outdoor dining
Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy

Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy

Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy
Cortona
10.0 out of 10, Exceptional, (27)
"Great location with gorgeous views over the Chiana hills, and nearby restaurants. We enjoyed discovering Cortona and several hill towns in the ares"
United States
Patricia H.
The price is ￥52,831
￥60,227 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy
Front of property - evening/night
Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
Casanova - Panoramic Rooms and Suites
Exterior detail
Cortonas Rooftop Nest

Cortonas Rooftop Nest

Cortonas Rooftop Nest
Cortona Old Town
10.0 out of 10, Exceptional, (11)
"Absolute gem of a property. Margherita is an excellent host as well!"
United States
Robin F.
The price is ￥26,375
￥30,430 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cortonas Rooftop Nest
Free daily cooked-to-order breakfast
San Michele al Borgo

San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is ￥18,618
￥21,216 total
includes taxes & fees
Jan 27 - Jan 28, 2026
San Michele al Borgo
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 ￥16,558
￥19,870 total
includes taxes & fees
Dec 28 - Dec 29
House in the Cortona countryside
Dining
Piazza Grande Boutique Apartment

Piazza Grande Boutique Apartment

Piazza Grande Boutique Apartment
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1)
"Le top ! Une localisation parfaite et un appartement comme rarement connu dans mes diverses locations, au point où nous avons souhaité y rester pour dîner avec repas traiteur. &#x1f929;Merci "
France
Gilles D.
The price is ￥67,519
￥93,644 total
includes taxes & fees
Dec 28 - Dec 29
Piazza Grande Boutique Apartment
Fridge, microwave, oven, stovetop
Apartment 'Entro le mura' with Balcony & Wi-Fi

Apartment 'Entro le mura' with Balcony & Wi-Fi

Apartment 'Entro le mura' with Balcony & Wi-Fi
Montepulciano
9.6 out of 10, Exceptional, (10)
"Lov the view, great location. Clean"
United States
David &amp; Teri B.
The price is ￥52,596
￥64,572 total
includes taxes & fees
Dec 28 - Dec 29
Apartment 'Entro le mura' with Balcony & Wi-Fi
Lobby lounge
Villa Cassia di Baccano

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ￥18,152
￥19,967 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Villa Cassia di Baccano
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Dimora del Poggio - cozy Tuscan apartment

Dimora del Poggio - cozy Tuscan apartment

Dimora del Poggio - cozy Tuscan apartment
San Quirico d'Orcia
10.0 out of 10, Exceptional, (4)
"Our hosts were fantastic, the apartment was clean, roomy, and comfortable, and the location was perfect. Easy walk to enjoy shops and dining."
United States
Joe B.
The price is ￥21,893
￥30,908 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Dimora del Poggio - cozy Tuscan apartment
Property grounds
La casa di Laura

La casa di Laura

La casa di Laura
Cortona Old Town
10.0 out of 10, Exceptional, (1)
"Best sleep I’ve had in a long time. Very quiet area. Beautiful views. Absolutely gorgeous. Water and coffee were provided. Clean. Bruno was very patient with us with the language barrier. We also had trouble getting to the place because we were not getting service on our phone till we connected to WiFi. Bruno met us and showed us where to park after showing us the way to the apartment. Very steep climb up to the apartment from the parking area, but Cortona is overall steep. You will climb up...
United States
Angie F.
The price is ￥16,558
￥31,828 total
includes taxes & fees
Jan 8 - Jan 9, 2026
La casa di Laura
1 bedroom, desk, iron/ironing board, free WiFi
Dragoncello Suite with four-poster bed

Dragoncello Suite with four-poster bed

Dragoncello Suite with four-poster bed
Montepulciano
10.0 out of 10, Exceptional, (3)
"My husband and I stayed here for our honeymoon/babymoon and had the BEST time! Francesca was so kind and helpful from start to finish. Our only regret is that we didn't stay here longer!"
United States
Katija S.
The price is ￥27,596
￥27,596 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Dragoncello Suite with four-poster bed
Suite Bernardo, Panoramica al terzo piano senza ascensore | 1 bedroom, desk, laptop workspace, iron/ironing board
PienzaLettings Suites

PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (1)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is ￥13,386
￥15,461 total
includes taxes & fees
Jan 6 - Jan 7, 2026
PienzaLettings Suites
Outdoor dining
Il Podere di Casa Rossa Pienza

Il Podere di Casa Rossa Pienza

Il Podere di Casa Rossa Pienza
Pienza
10.0 out of 10, Exceptional, (3)
"Wonderful views, accommodating hosts"
United States
Pete and Alison C.
The price is ￥34,771
￥50,593 total
includes taxes & fees
Dec 29 - Dec 30
Il Podere di Casa Rossa Pienza
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pozzo 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 9 days ago
Monastero di Cortona Hotel & Spa

Find out more about Pozzo

Search for holiday rentals in Pozzo on Expedia! You can easily find your home rentals, villas, holiday apartments in Pozzo using one of the methods below:

  • View our selection of featured holiday rentals in Pozzo
  • Use the map to find apartments and other holiday homes in the Pozzo neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pozzo while they last

Look no further and take a look at our great range of rental properties in Pozzo!

Frequently asked questions

Can I find a vacation rental in Pozzo?

Yes, there are vacation rentals near top local attractions in Pozzo, or you can choose a more secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Pozzo?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: This vacation home rental outside of Pozzo is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a terrace, a garden, and a selection of books so you can immerse yourself in your vacation.

What’s there to see and do in Pozzo?

Explore the area and family-friendly sights such as Berardenga Riding Centre, or get out into nature at a spot like Terme Antica Querciolaia. In the larger area, you’ll find Parrocchia S. Biago and Valdichiana Outlet Village.

What’s a vacation rental in Pozzo like?

Vacation rentals are privately owned properties where you can stay for a long or short time in Pozzo. Vacation rentals offer amenities like laundry facilities and kitchens so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a family getaway.