San Secondo Vacation Rentals

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

Vacation Rentals in San Secondo

Tenuta Borgo San Michele
Exterior detail

Tenuta Borgo San Michele

9.0 out of 10, Wonderful, (4)
"Breakfast was great. The rain brought to many insects. "
$87 nightly
The price is $101
Oct 8 - Oct 9
Total with taxes and fees
Tenuta Borgo San Michele
Farmhouse in the hills with panoramic view and swimming pool
Pool

Farmhouse in the hills with panoramic view and swimming pool

9.6 out of 10, Exceptional, (74)
"We‘ve spent two wonderful weeks with our two year old daughter and our dog. The house is beautifully located in the hills with no direct neighbours. The view is fantastic and we felt immediately at home in this beautiful house. We had a wonderful time and our hosts were just lovely. (We cannot say anything about the pool - except that it is huge - because we were there out of season in March when the pool was closed.)"
Farmhouse in the hills with panoramic view and swimming pool
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Outdoor dining

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

9.6 out of 10, Exceptional, (71)
"My husband and I loved our stay here! It was so close to town and the terrace was absolutely stunning. Would definitely stay here again! "
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Agriturismo Borgo Spagnoli
Romantic Suite, 1 Queen Bed, Kitchen, Courtyard View (Torchio) | Private kitchen | Fridge, oven, stovetop, coffee/tea maker

Agriturismo Borgo Spagnoli

8.8 out of 10, Excellent, (11)
"Hostess very kind and engaging. Had nice map of the area with suggested places to visit."
Agriturismo Borgo Spagnoli
Camping Villaggio Cerquestra
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas

Camping Villaggio Cerquestra

3.0 star property
9.0 out of 10, Wonderful, (21)
"Staff molto cordiale e disponibile. "
$56 nightly
The price is $65
Oct 2 - Oct 3
Total with taxes and fees
Camping Villaggio Cerquestra
17th century farmhouse with private pool and Wi-Fi and air conditioning
Outdoor pool

17th century farmhouse with private pool and Wi-Fi and air conditioning

9.2 out of 10, Wonderful, (39)
"Our host Maurizio, added quite a few extra layers of enjoyment to our stay. A brilliant host who went above and beyond to make our holiday truely memorable! We have invited him to come stay with us when he visits Australia. As for the farm house it’s self, an amazing experience to live like a true Italian. If you want to experience country life, I recommend La Rustica! Thank you Maurizio and Simonetta. ❤️"
17th century farmhouse with private pool and Wi-Fi and air conditioning
Luxury Cortona view hilltop Villa
Outdoor dining

Luxury Cortona view hilltop Villa

10.0 out of 10, Exceptional, (48)
"Perfect location for day trips covering so many of the hilltop towns. Perfect accommodation for a group of 12 friends as each bedroom has it’s own bathroom.Perfect Villa for relaxing at home coffee every morning, lying by the pool and dinner watching the incredible sunsets.Perfect hosts. Denise takes care of everything while you are at the villa including cooking us a wonderful dinner. Mieke answered all our questions prior to our arrival very promptly. She has set the villa up perfectly and...
Luxury Cortona view hilltop Villa
Villa Graziella, Romantic Perugia
Outdoor pool

Villa Graziella, Romantic Perugia

9.6 out of 10, Exceptional, (7)
"Great place. Would stay here again."
$197 nightly
The price is $197
Oct 2 - Oct 3
Total with taxes and fees
Villa Graziella, Romantic Perugia
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Fridge, microwave, oven, stovetop

Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)

10.0 out of 10, Exceptional, (132)
"This was the absolute best part of our time in Italy. This house is just amazing, and Stefano is the most generous and charming host. The house is clean, well provisioned, and has historic significance with modern comforts. What a treat to stay in this wonderful house that is close to everything. "
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv
Property grounds

Beautiful renovated stone villa - private pool,park,air conditioning,smart tv

9.8 out of 10, Exceptional, (35)
"We love our stay st Ca de Santi. Everything was great and the property is really amazing. You feel the Tuscany atmosphere."
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Dining

Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.

9.4 out of 10, Exceptional, (12)
"Surrounding very nice and quiet. Accomodation very comfortable and huge garden. Large Shilling pool. Everything compiled to have a very nice stay."
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Villa with swimming pool and garden- San Feliciano, Trasimeno lake
Pool

Villa with swimming pool and garden- San Feliciano, Trasimeno lake

8.4 out of 10, Very Good, (46)
"We had a great Family Holiday there. We enjoyed the pool so much and the nice terrasse, where we had all our meals and sat in the evenings to watch the Sunset on the lake. We liked the dogs visiting us and Massimo was always helpful."
Villa with swimming pool and garden- San Feliciano, Trasimeno lake
Agriturismo Nestore
Seasonal outdoor pool

Agriturismo Nestore

9.8 out of 10, Exceptional, (6)
"Foi tudo bem. Lugar simples mas muito agradável. "
Agriturismo Nestore
ancient villa with pool and park in total privacy
Outdoor pool

ancient villa with pool and park in total privacy

9.6 out of 10, Exceptional, (30)
"We had a great stay and enjoyed the historical house, the lovely and mystic garden with fireflies at night and the highlight is the pool, surrounded by trees giving privacy.We have booked our next stay for 2026 already.The house is secured by a fence, to the dogs could stay in the garden all day."
ancient villa with pool and park in total privacy
House with garden and panoramic view over Lake Trasimeno
Pool

House with garden and panoramic view over Lake Trasimeno

9.8 out of 10, Exceptional, (47)
"Beautiful location, very handy for the lake (swimming, pedelos etc) and with some lovely restaurants and gelatos in the local town! Views from the property are amazing, it is very quiet and peaceful"
House with garden and panoramic view over Lake Trasimeno
Exclusive hideaway nestled in woods with stunning lakeview Tuscany/Umbria border
Outdoor pool

Exclusive hideaway nestled in woods with stunning lakeview Tuscany/Umbria border

10.0 out of 10, Exceptional, (101)
"Lovely location, character property, well equipped, good pool and barbecue area. Excellent local restaurant recommendations. Hosts helped ensure we had everything we needed for relaxing, lazy stay."
Exclusive hideaway nestled in woods with stunning lakeview Tuscany/Umbria border
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Outdoor dining

Casa Bacco - private house with a remarkable garden in the centre of Cortona

10.0 out of 10, Exceptional, (8)
"This is a lovely property. Plenty of room. Well equipped with everything you need. The courtyard is a beautiful place for breakfast in the morning and wine in the evening. The flowers planted in the courtyard are beautiful. Please be aware that you must be able to walk up steep hills to get to this property. Of course, pretty much anywhere you go in Cortona is a hill."
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Beautiful Tuscan Villa with large garden and ample outside space
Outdoor pool, a heated pool

Beautiful Tuscan Villa with large garden and ample outside space

10.0 out of 10, Exceptional, (57)
"Our stay was really nice. The house is wonderful, the pool and the garden also. The kitchen is huge Just right for 8 people. The sight from the pool over the hills is great"
Beautiful Tuscan Villa with large garden and ample outside space
houses / villas - 6 rooms - 7/11 persons
Outdoor pool

houses / villas - 6 rooms - 7/11 persons

9.8 out of 10, Exceptional, (47)
"A lovely property, with lots of charm. We had a great stay and the hosts were very helpful. "
houses / villas - 6 rooms - 7/11 persons
Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo
Outdoor pool

Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo

10.0 out of 10, Exceptional, (18)
"This worked out really well for our extended family across 3 generations. Lots of space, great amenities, and we loved Arezzo. Liliana is a brilliant host"
$2,877 nightly
The price is $2,884
Oct 31 - Nov 1
Total with taxes and fees
Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo
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, unique property! Stunning views of the countryside. The staff were all very helpful and friendly. We will definitely recommend!"
Brian 3-night trip
Posted 3 days ago
Monastero di Cortona Hotel & Spa

Find out more about San Secondo

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 $65 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Agriturismo Borgo Spagnoli: This vacation home rental near San Secondo is located in a regional park and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. Kick off your shoes and enjoy yourself with a rooftop terrace and a private yard.

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 Monte Tezio. Historic Town Montone and Civitella Ranieri Castle 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.