Sestino Holiday Rentals

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Our top choices for Sestino holiday rentals

Locanda Guidi

Locanda Guidi
Sansepolcro
9.0 out of 10, Wonderful, (2)
"No one in reception on arrival or departure. Only one small bottle of water in the room. ID cards left in the entry hall with no supervision. Very nice room, excellent location, very clean but totally lacking in "accoglienza"."
Ireland
Michael
Locanda Guidi

Dolce Rosa Centro Storico

Dolce Rosa Centro Storico
Sansepolcro
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

Locanda del Viandante

Locanda del Viandante
Anghiari
9.0 out of 10, Wonderful, (6)
"Smuk beliggenhed - meget autentisk på den gode måde"
Denmark
tina
The price is NZ$272
includes taxes & fees
3 Jan - 4 Jan 2026
Locanda del Viandante

Elegant Countryside Retreat

Elegant Countryside Retreat
Città di Castello
The price is NZ$339
includes taxes & fees
12 Jan - 13 Jan 2026
Elegant Countryside Retreat

Residence Città Ideale

Residence Città Ideale
Urbino
7.4 out of 10, Good, (6)
The price is NZ$132
includes taxes & fees
13 Jan - 14 Jan 2026
Residence Città Ideale

Camera con Vista

Camera con Vista
Cagli
The price is NZ$147
includes taxes & fees
31 Dec - 1 Jan 2026
Camera con Vista

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$294
includes taxes & fees
10 Jan - 11 Jan 2026
Rustic Holiday Home in Citta di Castello With Swimming Pool

Casa Singola Esclusiva

Casa Singola Esclusiva
Mercato Saraceno
Casa Singola Esclusiva

Cottage La Fagianaia

Cottage La Fagianaia
Anghiari
The price is NZ$299
includes taxes & fees
31 Dec - 1 Jan 2026
Cottage La Fagianaia

Teo's house is the ideal home for relaxation, centrally located in Anghiari

Teo's house is the ideal home for relaxation, centrally located in Anghiari
Anghiari
10.0 out of 10, Exceptional, (1)
"The apartment was clean and cozy. I thoroughly enjoyed my stay. It is located on Corso Giacomo Matteotti and directly across from the main town square. Although not in the walled, traditional historic center, its in a very convenient and central location for exploring the entire town. The host Francesca was extremely helpful and checked in often."
United States
Danna J.
The price is NZ$470
includes taxes & fees
4 Jan - 5 Jan 2026
Teo's house is the ideal home for relaxation, centrally located in Anghiari

House "Joy" within walking distance of San Marino

House "Joy" within walking distance of San Marino
Emilia-Romagna
10.0 out of 10, Exceptional, (1)
"Tolle Wohnung mit perfekter Ausstattung. Balkon und Terrasse. Und hat es an nichts gefehlt. Lage ist ok, ca 30 min zu den Stränden und 20 Minuten nach San Marino Altstadt. Gastgeberin sehr freundlich und immer erreichbar. "
Germany
Sandra S.
The price is NZ$259
includes taxes & fees
29 Dec - 30 Dec
House "Joy" within walking distance of San Marino

Holiday Home in Umbria near Renaissance Castle

Holiday Home in Umbria near Renaissance Castle
Città di Castello
The price is NZ$290
includes taxes & fees
10 Jan - 11 Jan 2026
Holiday Home in Umbria near Renaissance Castle

Detached house for relaxation in the center of Anghiari

Detached house for relaxation in the center of Anghiari
Anghiari
The price is NZ$393
includes taxes & fees
1 Jan - 2 Jan 2026
Detached house for relaxation in the center of Anghiari

Villa Santarsa, 31 people, magnificent views and private pool, no neighbors

Villa Santarsa, 31 people, magnificent views and private pool, no neighbors
Sansepolcro
10.0 out of 10, Exceptional, (16)
"We had a great time, despite the heat. It's a bit of a drive up the mountain to Santarsa specifically, so make sure you have enough cars!"
United States
Donnacha F.
The price is NZ$2,949
includes taxes & fees
29 Dec - 30 Dec
Villa Santarsa, 31 people, magnificent views and private pool, no neighbors

lovely panorama, pool and valley view, equipped with kitchenette.

lovely panorama, pool and valley view, equipped with kitchenette.
Cagli
The price is NZ$311
includes taxes & fees
23 Jan - 24 Jan 2026
lovely panorama, pool and valley view, equipped with kitchenette.

Elegance and relaxation in an exclusive ground floor apartment flooded with light.

Elegance and relaxation in an exclusive ground floor apartment flooded with light.
Carpegna
The price is NZ$258
includes taxes & fees
2 Jan - 3 Jan 2026
Elegance and relaxation in an exclusive ground floor apartment flooded with light.

Villa Cantone with view, private pool and private SPA, perfect for groups!

Villa Cantone with view, private pool and private SPA, perfect for groups!
Sansepolcro
10.0 out of 10, Exceptional, (15)
"Villa Cantone was perfect for our family group of 22 people. It meet all our needs and provided us with the holiday of a lifetime. The hosts were very attentive and nothing seemed too much for them."
Australia
Geoffrey P.
The price is NZ$3,257
includes taxes & fees
28 Dec - 29 Dec
Villa Cantone with view, private pool and private SPA, perfect for groups!

1 Bedroom Apartment in Citerna

1 Bedroom Apartment in Citerna
Citerna
The price is NZ$238
includes taxes & fees
25 Jan - 26 Jan 2026
1 Bedroom Apartment in Citerna

"Fano" Studio 2 - Pool, home restaurant, Holidays, Truffles

"Fano" Studio 2 - Pool, home restaurant, Holidays, Truffles
CAGLI
The price is NZ$329
includes taxes & fees
26 Dec - 27 Dec
"Fano" Studio 2 - Pool, home restaurant, Holidays, Truffles
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 Sestino Hotel Reviews

Find out more about Sestino

Everything you need to know about Sestino holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sestino holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Sestino holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sestino holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sestino holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sestino holiday rentals we have selected for you start as low as NZ$132 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sestino rentals

At Expedia, we put the best Sestino holiday 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 Sestino 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 Sestino holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sestino. 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

Can I find holiday rentals in Sestino?

Yes, there are holiday rentals close to the most popular sights in Sestino, 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 Sestino has to offer?

Old Tuscan farmhouse with salt pool, soccer/volleyball field, barbecue: This holiday home rental outside of Sestino is located in the mountains, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Sestino?

Choose from 6 Expedia holiday rentals in Sestino for a memorable holiday.

What’s there to see and do in Sestino?

While exploring the area, visit family-friendly sights like Aboca Museum, or get outside and enjoy nature at Sasso di Simone. Eremo Monte Carpegna and Lago di Mercatale - Sassocorvaro are a couple of places you'll find in the wider area.

What’s a holiday rental in Sestino like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sestino. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for families.