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San Secondo Holiday Rentals

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Our top choices for San Secondo holiday rentals

1. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (40 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is NZ$158
includes taxes & fees
25 Oct - 26 Oct
iConic Wellness Resort

2. Elegant Countryside Retreat

Elegant Countryside Retreat
Città di Castello
9.4 out of 10, Exceptional, (29 reviews)
"Enjoyed evenings near that fireplace, really nice ambiance when winding down after excursions into town. Garden’s a good spot to chill if you want some fresh air as well."
United States
Anonymous traveller
The price is NZ$504
includes taxes & fees
10 Oct - 11 Oct
Elegant Countryside Retreat

3. Dolce Rosa Centro Storico

Dolce Rosa Centro Storico
Sansepolcro
9.6 out of 10, Exceptional, (13 reviews)
"Ottimo rapporto qualità prezzo camera carina... un unico neo mancavano i tappi di vasca e bidet..."
Italy
Sergio
The price is NZ$106
includes taxes & fees
4 Nov - 5 Nov
Dolce Rosa Centro Storico

4. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is NZ$283
includes taxes & fees
2 Nov - 3 Nov
B&B Piccolo Hotel

5. 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$428
includes taxes & fees
21 Oct - 22 Oct
Rustic Holiday Home in Citta di Castello With Swimming Pool

6. Holiday Home in Umbria near Renaissance Castle

Holiday Home in Umbria near Renaissance Castle
Città di Castello
9.6 out of 10, Exceptional, (12 reviews)
"Slept well each night with minimal fuss checking in or out. The rooms were tidy and welcoming for quick resets before heading out."
United States
Anonymous traveller
The price is NZ$431
includes taxes & fees
8 Oct - 9 Oct
Holiday Home in Umbria near Renaissance Castle

7. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
10.0 out of 10, Exceptional, (3 reviews)
"I really liked the brand new room. Nice design and super comfy bed. Plus free coffee is a nice addition to the experience there. Loved it. Plus my personal highlight were the nice views into the historical center of Arezzo."
Germany
Florian
The price is NZ$147
includes taxes & fees
11 Oct - 12 Oct
Limehome Arezzo Duomo

8. Apartment 'Glicine ad Antico Casale '700' with Shared Pool & Wi-Fi

Apartment 'Glicine ad Antico Casale '700' with Shared Pool & Wi-Fi
Umbertide
The price is NZ$732
includes taxes & fees
30 Oct - 31 Oct
Apartment 'Glicine ad Antico Casale '700' with Shared Pool & Wi-Fi

9. San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is NZ$268
includes taxes & fees
9 Oct - 10 Oct
San Michele al Borgo

10. L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
The price is NZ$110
includes taxes & fees
28 Oct - 29 Oct
L'Antica Sosta

11. -2 / 3-seater garage with private garden, swimming pool, park and spa

-2 / 3-seater garage with private garden, swimming pool, park and spa
sansepolcro (arezzo)
9.6 out of 10, Exceptional, (4 reviews)
"Es waren traumhafte Tage. So extrem ruhig ..... Richtig entspannend. Alles da zur Selbstversorgung an Küchenutensilien. Alles sehr sauber. Der Besitzer sehr freundlich und bemüht. Wir fahren nächstes Jahr wieder hin ..... Aber länger. Sehr empfehlenswert"
Austria
Margit H.
The price is NZ$326
includes taxes & fees
8 Oct - 9 Oct
-2 / 3-seater garage with private garden, swimming pool, park and spa

12. Beb 1416 Room with Shared Terrace, Shared Garden, and Wi-Fi

Beb 1416 Room with Shared Terrace, Shared Garden, and Wi-Fi
ANGHIARI
10.0 out of 10, Exceptional, (1 review)
"I greatly enjoyed my stay at this beautiful and unique apartment. It was captivatingly decorated with antiques and appointed with all needed amenities. the hosts were charming and helpful, and made every effort to make me feel at home and my stay comfortable. If I had the time, I believe a longer stay would have been quite pleasant."
United States
Andrew P.
The price is NZ$213
includes taxes & fees
8 Oct - 9 Oct
Beb 1416 Room with Shared Terrace, Shared Garden, and Wi-Fi

13. Apartment 'Sotto Le Mura' with Wi-Fi

Apartment 'Sotto Le Mura' with Wi-Fi
Anghiari
The price is NZ$190
includes taxes & fees
8 Oct - 9 Oct
Apartment 'Sotto Le Mura' with Wi-Fi

14. Wohnung la Mimosa by Interhome

Wohnung la Mimosa by Interhome
Cortona
The price is NZ$418
includes taxes & fees
14 Oct - 15 Oct
Wohnung la Mimosa by Interhome

15. 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, (4 reviews)
"The place was amazing and as advertised! We enjoyed the area very much, the views are amazing! We shopped at the local market and enjoyed dinner in both nights we were there. If we are back in the area, we will stay here again! Saverio was very attentive and gracious. Check in and out couldn’t have been easier! "
United States
John L.
The price is NZ$261
includes taxes & fees
13 Oct - 14 Oct
Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!

16. The Cyclist. Pedal your way to your ideal stay!

The Cyclist. Pedal your way to your ideal stay!
Parlesca
The price is NZ$195
includes taxes & fees
10 Oct - 11 Oct
The Cyclist. Pedal your way to your ideal stay!

17. Apartment 'Magnolia Antico Casale '700' with Shared Pool and Wi-Fi

Apartment 'Magnolia Antico Casale '700' with Shared Pool and Wi-Fi
Umbertide
The price is NZ$1,026
includes taxes & fees
30 Oct - 31 Oct
Apartment 'Magnolia Antico Casale '700' with Shared Pool and Wi-Fi

18. Locanda del Viandante

Locanda del Viandante
Anghiari
9.0 out of 10, Wonderful, (6 reviews)
"客室は清潔で、とても可愛いかったです。宿泊場所からの眺望は感動します。 朝食が人生でベスト朝食でした!"
Japan
Tatsuya
The price is NZ$240
includes taxes & fees
8 Oct - 9 Oct
Locanda del Viandante

19. The Garden Above the clouds

The Garden Above the clouds
Nuvole
The price is NZ$616
includes taxes & fees
4 Nov - 5 Nov
The Garden Above the clouds

20. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful location. Can't wait to go back."
United States
Dawn H.
The price is NZ$195
includes taxes & fees
13 Oct - 14 Oct
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
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

Find out more about San Secondo

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our San Secondo holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up San Secondo. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in San Secondo. Seeing all the best attractions is bound to make you fall in love with San Secondo. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in San Secondo short-term rentals, that won’t be hard to do.

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 are some of the best holiday rentals that San Secondo has to offer?

Holiday Home in Umbria with Pool: This holiday home rental outside of San Secondo offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

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 Battle of Lake Trasimene Monument. Historic Town Montone and Madonna del Parto Museum 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.