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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 San Secondo holiday rentals

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 2.422.016 ₫
2.850.160 ₫ total
includes taxes & fees
18 Jan - 19 Jan 2026
Cameracaffè Centro
Exterior
L'Antica Sosta

Townhouse in Corciano

L'Antica Sosta
9.4 out of 10, Exceptional, (3)
"Molto accoglienti e gentili "
Italy
Valentina
The price is 1.830.341 ₫
2.013.375 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
L'Antica Sosta
Exterior detail
Tenuta Borgo San Michele

Aparthotel in Gubbio

Tenuta Borgo San Michele
9.2 out of 10, Wonderful, (5)
"Un posto davvero tranquillo immenso nel verde. Colazione abbondante e variegata. Gentilissimo il signore alla reception che ci ha dato consigli per vivere al meglio il nostro soggiorno."
Italy
Laura
The price is 3.490.061 ₫
3.962.322 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Tenuta Borgo San Michele
Balcony
Dolce Rosa Centro Storico

Townhouse in Sansepolcro

Dolce Rosa Centro Storico
9.6 out of 10, Exceptional, (13)
"Ottimo rapporto qualità prezzo camera carina... un unico neo mancavano i tappi di vasca e bidet..."
Italy
Sergio
Dolce Rosa Centro Storico
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 3.389.520 ₫
3.851.727 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
San Michele al Borgo
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 2.117.750 ₫
2.514.407 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
B&B 52cento
Lunch, dinner served; Italian cuisine, garden views
Locanda del Viandante

Townhouse in Anghiari

Locanda del Viandante
9.0 out of 10, Wonderful, (6)
"Smuk beliggenhed - meget autentisk på den gode måde"
Denmark
tina
The price is 3.781.780 ₫
4.159.866 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Locanda del Viandante
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
Comfort Apartment, 3 Bedrooms | View from property
Rustic Holiday Home in Citta di Castello With Swimming Pool

Holiday Home in Città di Castello

Rustic Holiday Home in Citta di Castello With Swimming Pool
The price is 4.123.449 ₫
4.535.794 ₫ total
includes taxes & fees
10 Jan - 11 Jan 2026
Rustic Holiday Home in Citta di Castello With Swimming Pool
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 San Secondo 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 5 days ago
Monastero di Cortona Hotel & Spa

Frequently asked questions

Are there holiday rentals in San Secondo?

Yes, there are holiday rentals close to the most popular sights in San Secondo, or you can select a more secluded option if you're looking for a relaxing stay.

What’s there to see and do in San Secondo?

Explore the area and family-friendly sights such as Aboca Museum, or get out into nature at a spot like Sualzo Beach. Vitelli Palace alla Cannoniera and Historic Town Montone are a couple of places you'll find in the wider area.

What’s a holiday rental in San Secondo like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in San Secondo. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.