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Check prices for these dates

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

Our top choices for Pescaia holiday rentals

Lobby lounge
Villa Cassia di Baccano

Townhouse in Loro Ciuffenna

Villa Cassia di Baccano
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ฿4,529
฿4,982 total
includes taxes & fees
7 Jan - 8 Jan 2026
Villa Cassia di Baccano
View from room
Abbadia Sicille Relais

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ฿2,527
฿2,890 total
includes taxes & fees
6 Jan - 7 Jan 2026
Abbadia Sicille Relais
Lobby
Residenza Fabroni

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is ฿2,744
฿3,165 total
includes taxes & fees
13 Jan - 14 Jan 2026
Residenza Fabroni
Suite Bernardo, Panoramica al terzo piano senza ascensore | 1 bedroom, desk, laptop workspace, iron/ironing board
PienzaLettings Suites

Townhouse in Pienza

PienzaLettings Suites
10.0 out of 10, Exceptional, (1)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is ฿2,640
฿3,052 total
includes taxes & fees
23 Dec - 24 Dec
PienzaLettings Suites
Deluxe Double Room | View from room
Affitacamere Maria Gabriella

Townhouse in Pienza

Affitacamere Maria Gabriella
9.8 out of 10, Exceptional, (51)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella
Balcony
Cameracaffè Centro

Townhouse in Arezzo Centro Storico

Cameracaffè Centro
8.6 out of 10, Excellent, (179)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
The price is ฿3,043
฿3,567 total
includes taxes & fees
11 Jan - 12 Jan 2026
Cameracaffè Centro
Exterior
Meublé Il Riccio

Townhouse in Montepulciano

Meublé Il Riccio
9.8 out of 10, Exceptional, (86)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
Meublé Il Riccio
Breakfast, lunch, dinner served; local cuisine
Hotel San Gregorio

Residence in Pienza

Hotel San Gregorio
3.0 star property
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is ฿6,302
฿7,152 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio
Luxury Room, Jetted Tub, City View | Free WiFi, bed sheets
B&B 52cento

Townhouse in Arezzo Centro Storico

B&B 52cento
8.0 out of 10, Very good, (73)
"Exactly how it is described and very near the train station. Walkable distance to all the things to do around there. I really enjoyed my stay there. "
United States
Maria de Lourdes
The price is ฿2,528
฿3,001 total
includes taxes & fees
8 Jan - 9 Jan 2026
B&B 52cento
Exterior
Bed & Breakfast Vicolo dell'Oste

Townhouse in Montepulciano

Bed & Breakfast Vicolo dell'Oste
9.6 out of 10, Exceptional, (128)
"Great hosts, central location "
United States
Alexander
The price is ฿3,911
฿4,449 total
includes taxes & fees
23 Dec - 24 Dec
Bed & Breakfast Vicolo dell'Oste
Classic Double or Twin Room, 1 Double Bed | Premium bedding, down duvets, pillow-top beds, minibar
THE MONNA LISA RESORT

Townhouse in Arezzo

THE MONNA LISA RESORT
9.6 out of 10, Exceptional, (8)
"Massimiliano was a great host, but we were the only guests and the restaurant was closed. The hotel was basically unmanaged. It should not have been listed as a hotel. "
United States
Bart
The price is ฿4,664
฿5,351 total
includes taxes & fees
1 Jan - 2 Jan 2026
THE MONNA LISA RESORT
Free daily cooked-to-order breakfast
San Michele al Borgo

Townhouse in Castiglion Fiorentino

San Michele al Borgo
9.8 out of 10, Exceptional, (9)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is ฿4,046
฿4,597 total
includes taxes & fees
7 Jan - 8 Jan 2026
San Michele al Borgo
Camera Superior, vista città, primo piano senza ascensore | Laptop workspace, iron/ironing board, free WiFi
TuscanyLettings Studio&Room

Townhouse in Pienza

TuscanyLettings Studio&Room
10.0 out of 10, Exceptional, (1)
"メイン通りの好立地。 客室は豪華でエレガント。 ウェルカムキットも良く、アメニティも良好。 次回も必ず利用したい。 スタッフの方、いろいろありがとうございました。"
Japan
keita
The price is ฿2,973
฿3,417 total
includes taxes & fees
6 Jan - 7 Jan 2026
TuscanyLettings Studio&Room
Daily buffet breakfast (EUR 10 per person)
DormiVeglia B&B

Townhouse in Monte San Savino

DormiVeglia B&B
10.0 out of 10, Exceptional, (27)
"This was our favourite B&B. The owner Simona was absolutely wonderful. The hot tub in our room was out of this world. If you have the chance to visite this gem…DO IT!!"
Canada
Claude
DormiVeglia B&B
Premium bedding, down duvets, minibar, in-room safe
La Locanda di San Francesco

Townhouse in Montepulciano

La Locanda di San Francesco
9.8 out of 10, Exceptional, (131)
"Great room-great staff-great location"
United States
Richard
The price is ฿5,617
฿6,326 total
includes taxes & fees
18 Jan - 19 Jan 2026
La Locanda di San Francesco
Property entrance
Il Tosco

Residence in Montepulciano

Il Tosco
10.0 out of 10, Exceptional, (115)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is ฿8,305
฿9,283 total
includes taxes & fees
23 Dec - 24 Dec
Il Tosco
Business centre
Allegra Toscana - Affittacamere Guest house

Townhouse in Arezzo Centro Storico

Allegra Toscana - Affittacamere Guest house
7.0 out of 10, Good, (16)
"Great location in Arezzo, easy and simple to find and access. Everything was exactly as we needed although we did not need to stay long."
United Kingdom
Justin
Allegra Toscana - Affittacamere Guest house
Exterior
Podere La Chiusella

Aparthotel in Rapolano Terme

Podere La Chiusella
9.4 out of 10, Exceptional, (30)
"Et sjarmerende lite B&B. Har nok vært utrolig vakkert i sine glansdager, men områdene rundt bærer preg av lite vedlikehold. Leiligheten var helt grei for en overnatting. Gulvet på badet var ikke rent. Når vi tørket opp etter oss ble håndkleet møkkete. Men overnattingen var helt grei alt i alt. Når vi skulle sjekke ut var det ikke et menneske å se, resepsjonen var stengt. Endte med å sette nøklene i døra og dra da alt var betalt ved bestilling."
Norway
Elisabeth
Podere La Chiusella
Property grounds
Artisti del Cavallo Tourism

Villa in Foiano della Chiana

Artisti del Cavallo Tourism
8.4 out of 10, Very good, (24)
"Good house for one night. "
Germany
Heiner
The price is ฿2,668
฿3,008 total
includes taxes & fees
23 Dec - 24 Dec
Artisti del Cavallo Tourism
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 Pescaia 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 4 days ago
Monastero di Cortona Hotel & Spa

Find out more about Pescaia

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

  • View our selection of featured holiday rentals in Pescaia
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  • Enter your travel dates to view the best deals on holiday rentals in Pescaia while they last

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

Frequently asked questions

Are there holiday rentals in Pescaia?

Yes, there are holiday rentals close to the most popular sights in Pescaia, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Pescaia speak positively about the countryside and wineries in this destination. While you're here, grab a bite or have a drink at the local cheese shops.

What can I see and do in Pescaia?

Explore the area and cultural attractions such as Signorelli Theatre, or visit one of the family-friendly sights such as Berardenga Riding Centre. Valdichiana Outlet Village and Arezzo Equestrian Centre are a couple of places you'll find in the wider area.

What are holiday rentals like in Pescaia?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pescaia. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family trips.