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San Secondo Vacation Rentals

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for San Secondo vacation rentals

Pool

1. 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 $88
Nov 18 - Nov 19
Total with taxes and fees
iConic Wellness Resort
A courtyard with a stone pathway, potted plants, and a building with multiple windows and a door.

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

Rustic Holiday Home in Citta di Castello With Swimming Pool
Città di Castello
$262 nightly
The price is $283
Oct 29 - Oct 30
Total with taxes and fees
Rustic Holiday Home in Citta di Castello With Swimming Pool
A narrow street with historic buildings, a balcony with potted plants, and a no parking sign.

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
$55 nightly
The price is $61
Nov 16 - Nov 17
Total with taxes and fees
Dolce Rosa Centro Storico
A hotel room with a bed, a desk with a chair, a wardrobe, a television, and a window with curtains.

4. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
9.0 out of 10, Wonderful, (4 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
$84 nightly
The price is $99
Nov 2 - Nov 3
Total with taxes and fees
Limehome Arezzo Duomo
A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.

5. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.4 out of 10, Exceptional, (26 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
$142 nightly
The price is $158
Nov 7 - Nov 8
Total with taxes and fees
B&B Piccolo Hotel
A breakfast setting with a fireplace, a table with plates, glasses, and a croissant.

6. 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
$131 nightly
The price is $148
Oct 28 - Oct 29
Total with taxes and fees
San Michele al Borgo
A stone building with a balcony and a small garden area with plants.

7. L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
$57 nightly
The price is $62
Oct 29 - Oct 30
Total with taxes and fees
L'Antica Sosta
A stone building with a tiled roof, surrounded by lush green fields and mountains in the background.

8. 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 29 - Oct 30
Total with taxes and fees
Locanda del Viandante
A modern hotel room with large windows, a bed, a desk, and a chair.

9. B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.2 out of 10, Very good, (84 reviews)
"Very accessible and easy accommodation. Very pleasant room and reasonable breakfast. Within walking distance of train station and city centre."
Australia
Tina
$69 nightly
The price is $83
Nov 3 - Nov 4
Total with taxes and fees
B&B 52cento
A balcony with potted plants and a view of a cityscape.

10. Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (195 reviews)
"Pros: Nice staff. Good breakfast with a nice view. Cons: Old bed and can feel the metal springs in your back so poor sleep. Lots of beggars and vagrants at the entrance of building."
United States
Steven
$88 nightly
The price is $103
Nov 1 - Nov 2
Total with taxes and fees
Cameracaffè Centro
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

11. CASA AMBRA

CASA AMBRA
Cortona Old Town
$217 nightly
The price is $241
Nov 6 - Nov 7
Total with taxes and fees
CASA AMBRA
A sectional sofa with a chaise, positioned against a plain wall, on a wooden floor.

12. La Corte dei Servi - Locazione Turistica

La Corte dei Servi - Locazione Turistica
Sansepolcro
$181 nightly
The price is $199
Nov 3 - Nov 4
Total with taxes and fees
La Corte dei Servi - Locazione Turistica
Room

13. Bibi Boutique

Bibi Boutique
Arezzo Centro Storico
$77 nightly
The price is $91
Nov 3 - Nov 4
Total with taxes and fees
Bibi Boutique
A building entrance with a number '10' sign, a potted plant with flowers, and a staircase leading to the entrance.

14. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
$104 nightly
The price is $116
Nov 3 - Nov 4
Total with taxes and fees
Vicolo Della Scala Rooms - Il Sole
A narrow stone-walled room with a wooden table and blue upholstered chairs.

15. Allegra Toscana - Affittacamere & Guest House Arezzo

Allegra Toscana - Affittacamere & Guest House Arezzo
Arezzo Centro Storico
7.0 out of 10, Good, (17 reviews)
"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
$89 nightly
The price is $109
Nov 2 - Nov 3
Total with taxes and fees
Allegra Toscana - Affittacamere & Guest House Arezzo
A hotel room with a bed, two bedside tables, a painting on the wall, and a vase with flowers on one of the tables.

16. Room-two-room Apartment

Room-two-room Apartment
Saione
10.0 out of 10, Exceptional, (1 review)
"A little tricky to locate but friendly staff and very walkable to see the sites."
Canada
Thelma
$117 nightly
The price is $136
Nov 3 - Nov 4
Total with taxes and fees
Room-two-room Apartment
Room

17. Two-room Apartment for 3 People With Kitchen and Private Bathroom

Two-room Apartment for 3 People With Kitchen and Private Bathroom
Saione
8.0 out of 10, Very good, (1 review)
"The property is in a great location in Arezzo and the owner communicated clearly, thoroughly with us and this was much appreciated since we are still novice VRBO users. Not having a designated parking spot caused some frustration when we ended up finding an open spot a block away. "
United States
Robert
$134 nightly
The price is $154
Nov 1 - Nov 2
Total with taxes and fees
Two-room Apartment for 3 People With Kitchen and Private Bathroom
A building entrance with a number '10' sign, a potted plant with flowers, and a staircase leading to the entrance.

18. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
$96 nightly
The price is $108
Nov 3 - Nov 4
Total with taxes and fees
Vicolo Della Scala Rooms - La Luna
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
"Beautiful historic property well located with just enough to do. Very relaxing ."
Peter 4-night trip
Posted 1 day ago
Monastero di Cortona Hotel & Spa

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 $223 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.