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San Secondo Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for San Secondo vacation rentals

A building with a balcony, multiple windows, and a door.

1. 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
$51 nightly
The price is $56
Nov 16 - Nov 17
Total with taxes and fees
Dolce Rosa Centro Storico
Pool

2. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (41 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
$74 nightly
The price is $89
Nov 16 - Nov 17
Total with taxes and fees
iConic Wellness Resort
A stone building with a balcony and a small garden area with plants.

3. L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
$60 nightly
The price is $66
Oct 21 - Oct 22
Total with taxes and fees
L'Antica Sosta
A courtyard with a stone pathway, potted plants, and a building with multiple windows and a door.

4. 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 traveler
$285 nightly
The price is $285
Oct 21 - Oct 22
Total with taxes and fees
Elegant Countryside Retreat
A grassy courtyard with a stone wall, a wooden bench, and a building with a tower in the background.

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

Apartment 'Sotto Le Mura' with Wi-Fi
Anghiari
$107 nightly
The price is $107
Oct 21 - Oct 22
Total with taxes and fees
Apartment 'Sotto Le Mura' with Wi-Fi
A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

6. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
$71 nightly
The price is $75
Oct 18 - Oct 19
Total with taxes and fees
Happy Nest Tuscany Between Florence and Rome
A modern kitchen with a central island, built-in appliances, and a dining area with a table and chairs.

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

The Cyclist. Pedal your way to your ideal stay!
Parlesca
$109 nightly
The price is $109
Oct 23 - Oct 24
Total with taxes and fees
The Cyclist. Pedal your way to your ideal stay!
A modern kitchen with wooden cabinets, a microwave, and a black countertop.

8. 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
$68 nightly
The price is $81
Oct 18 - Oct 19
Total with taxes and fees
Limehome Arezzo Duomo
Holiday Home Exterior [summer]

9. 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)
"Good value overall considering included pool use and garden space. The location offered beautiful views that enhanced our relaxation throughout the stay."
United States
Anonymous traveler
$256 nightly
The price is $256
Oct 21 - Oct 22
Total with taxes and fees
Holiday Home in Umbria near Renaissance Castle
A rustic outdoor dining area with wooden tables and chairs, hanging birdcages, and a view of greenery.

10. 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.
$116 nightly
The price is $120
Oct 23 - Oct 24
Total with taxes and fees
Beb 1416 Room with Shared Terrace, Shared Garden, and Wi-Fi
A stone fireplace with a rustic mantel, a large vase, and a heart-shaped decoration on the wall.

11. The Garden Above the clouds

The Garden Above the clouds
Nuvole
$345 nightly
The price is $349
Nov 1 - Nov 2
Total with taxes and fees
The Garden Above the clouds
A courtyard with a stone pathway, potted plants, and a building with multiple windows and a door.

12. Rustic Holiday Home in Citta di Castello With Swimming Pool

Rustic Holiday Home in Citta di Castello With Swimming Pool
Città di Castello
$230 nightly
The price is $253
Oct 21 - Oct 22
Total with taxes and fees
Rustic Holiday Home in Citta di Castello With Swimming Pool
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

13. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
$95 nightly
The price is $107
Nov 6 - Nov 7
Total with taxes and fees
Vicolo Della Scala Rooms - La Luna
A stone building with a pool, surrounded by trees and outdoor seating.

14. -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)
8.4 out of 10, Very good, (5 reviews)
"Het uitzicht was prima, het bed lag ook wel goed, maar ventilatie was niks, waardoor het S’nachts bloedheet was. Het was een verouderde garage, ik zou niemand aanraden dit te boeken. Van park en spa heb ik ook niks gezien."
Netherlands
Sjoukje
$186 nightly
The price is $186
Oct 18 - Oct 19
Total with taxes and fees
-2 / 3-seater garage with private garden, swimming pool, park and spa
A room with a stone archway, wooden ceiling beams, a bed, a chair, a table, and a window with curtains.

15. Cozy apartment: Your oasis of paradise in the countryside

Cozy apartment: Your oasis of paradise in the countryside
Anghiari
$139 nightly
The price is $139
Oct 20 - Oct 21
Total with taxes and fees
Cozy apartment: Your oasis of paradise in the countryside
A cozy living room with a wooden ceiling, a sofa, a dining table with chairs, a bookshelf, and a view through a window.

16. La Perla del Lago Vacation Home - All the comforts of home with a view of the lake!

La Perla del Lago Vacation Home - All the comforts of home with a view of the lake!
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.
$142 nightly
The price is $146
Oct 29 - Oct 30
Total with taxes and fees
La Perla del Lago Vacation Home - All the comforts of home with a view of the lake!
A stone building with a sloped roof, a covered porch, and a small garden area with potted plants.

17. Apartment 'Lavanda ad Antico Casale '700' with Shared Pool & Wi-Fi

Apartment 'Lavanda ad Antico Casale '700' with Shared Pool & Wi-Fi
Umbertide
8.0 out of 10, Very good, (1 review)
"Pros: Location in the mountains is superb, very friendly& supportive staff, fair price Cons: Only very small windows in the appartment, thus dark and nearly no chance for fresh cold air in the night. Due to the size of the location the pool was overcrowded and too less sun chairs. Photos better than reality."
United States
Anonymous traveler
$345 nightly
The price is $345
Oct 18 - Oct 19
Total with taxes and fees
Apartment 'Lavanda ad Antico Casale '700' with Shared Pool & Wi-Fi
A table set outdoors with a view of mountains, including a basket of pastries, cups of coffee, and a bottle of water.

18. Locanda del Viandante

Locanda del Viandante
Anghiari
9.2 out of 10, Wonderful, (7 reviews)
"This is really one of those Dinner destinations that has rooms to stay too! 🙂 Beautiful location, and great food, I would have liked to have stayed longer!"
United States
Kenneth
$127 nightly
The price is $140
Oct 20 - Oct 21
Total with taxes and fees
Locanda del Viandante
An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

19. 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
$140 nightly
The price is $158
Oct 27 - Oct 28
Total with taxes and fees
B&B Piccolo Hotel
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

20. 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
$121 nightly
The price is $138
Nov 13 - Nov 14
Total with taxes and fees
San Michele al Borgo
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

Relais Villa Baldelli

Relais Villa Baldelli

10/10 Excellent
"Beautiful property and amazing service!"
Michael 7-night trip
Posted 2 days ago
Relais Villa Baldelli

Find out more about San Secondo

Everything you need to know about San Secondo vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the San Secondo vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect San Secondo vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

San Secondo vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in San Secondo. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit San Secondo in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $226 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on San Secondo rentals

At Expedia, we put the best San Secondo vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top San Secondo rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream San Secondo vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around San Secondo. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in San Secondo?

Yes, there are vacation rentals close to popular local attractions in San Secondo, or you can choose a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in San Secondo?

Holiday Home in Umbria with Pool: This vacation home rental near San Secondo offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection 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 larger area.

What’s a vacation rental in San Secondo like?

Vacation rentals are private properties you can book for a few weeks or just a few days in San Secondo. Vacation rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for families.