Holiday houses in San Leo

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in San Leo

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Prato, Italy

4.98 out of 5 average rating, 111 reviews

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our purple or turquoise apartment, there might still be availability. Purple: https://www.airbnb.com/rooms/plus/6867164 Turquoise: https://www.airbnb.com/rooms/plus/9430389 When we moved to Italy in 2008, we bought a couple of old country houses, and renovated them into spacious (90 m2, 900 sqft) luxurious gems. As we enjoy a nice house with a good atmosphere we ensured that the house is built with materials that represent Italy as it was, with: travertine floors, large beams from chestnut wood, exposed stone work, sinks crafted from local quarried stone ('pietra serena') etc.. During our travels through Italy we could not find modern, fresh, all comfort included houses and a good atmosphere for rent. Therefore, we decided to build it ourselves and we are ready to share our place with our guests. Our property has 3 similar sized houses that can of course be rented for a group of people. In total we can accommodate 6 persons. When you want to share meals there is ample room to seat everyone around the big table in one of the apartments or of course in the garden. You will find us in a small hamlet called Prato in the comune of Monte S.Maria Tiberina, 2 km from the border with Tuscany in the North of Umbria, in an area very close to the Marche. We value easy access. Our house is in a little village and as there is an asphalt road to the village, there is no need to drive for kilometers on a white (gravel) road to reach us. The next town, Città di Castello, is an easy 20 minutes drive. Here you can find everything you need from shops to food to restaurants and museums. Every apartment is built to be a separate unit, you have complete privacy with a private terrace and private entrance. The house is equipped with everything you may want on a holiday; Netflix, (free) wireless Internet throughout the whole house, a washer/dryer, air-conditioning in the bedrooms and mosquito nets on all windows and doors to give you a good night rest. For guests that are coming in autumn, winter or early spring we have a nice fireplace in the living room that also heats the radiators throughout the whole house. A plunge pool (3x7 m) is available for the guests from half May till half September. Your private terrace gives you all the privacy you'd want. There are no hidden costs. All costs are included in the price: end cleaning, electricity, heating (gas and/or firewood), bed linen (towels for every day should you want that) etc. We can help you make your stay as relaxed as possible. We know the area, speak Italian, provide recomendations and make bookings if needed. Umbria is renowned for its wine and food alike. Indulge in the picturesque surroundings and the wonderful gastronomy of the region. The area is a great place for outdoor activities including walking, cycling, playing golf, or horseback riding. Public transport does not come to our location. You will need a car; you can rent one from any of the agencies at the airports you can use to fly in. The Perugia airport is the closest by at 50 min, but also Firenze, Bologna, Pisa or Rome are all close by, with the furthest a 2,5 hour drive. When you want to dine out we offer a taxi service (for a small fee) where we bring you to the restaurant and pick you up again (in the villages surrounding our place). This way you can enjoy the food, wine (maybe a little grappa) etc. without having to worry about drinking and driving. In case you don't want to go out at all, we can prepare a gourmet dinner served in your own apartment for you as well. Naturally, breakfast or lunch won't be a problem either. On the day of your arrival, the first necessities will be waiting for you and if you want, we will get you the groceries you may need up front (just let us know what).

13–20 Nov

$433 NZD per night

Guest favourite

Home in Pietrarubbia, Italy

4.97 out of 5 average rating, 31 reviews

Galasterna; at the foot of the mountain

Recently renovated farmhouse that maintains original architectural features. The farmhouse is located in the Municipality of Pietrarubbia in the heart of Montefeltro and is surrounded by meadows and woods of evocative and pristine beauty. Recently renovated farmhouse that maintains all the architectural features of a rural agricultural building. Located in the Municipality of Pietrarubbia in the heart of Montefeltro on the north side with respect to the centre of the capital, in a wonderful panoramic position 700 m above sea level, it enjoys a cool and ideal climate to escape the summer aphids. From this position it is possible to see the most beautiful mountains of the Apennine ridge towards the south until you reach Monte Conero, and some typical towns of Montefeltro such as Sassocorvaro and Urbino. To the northwest is Mount Carpegna with its picturesque Ripa known as the "coast of jumps" that highlights the sandstone stratification of Mount Carpegna. It is possible to reach in a few kilometres small and important ancient villages such as San Leo, Montecerignone, Cavoleto, Frontino and many others that offer, especially in the summer, local festivals and medieval revisions for a dip in the past. The house is surrounded by meadows and woods of evocative beauty and a still unspoilt environment, inhabited in every corner by nature, a privileged guest and always present, offers an ideal place to rest your mind and body. Guests can access the entire structure using all the services provided Guests will be assisted by the staff of the structure for any eventuality or need. In addition, the staff will be happy to illustrate nature trails and itineraries and suggest popular events in the surrounding area. Pietrarubbia is a hilly town of medieval origins. The town is dominated by the majestic summit of Mount Carpegna, which shows steep slopes on this side, with thick beeches alternating with bare rock; allaround there is a varied mosaic of crops, forests and, here and there, sharp rocky spurs dominated by ancient fortresses. The ancient village is just steps away and deserves your attention. The vast territory around the house is magnificent to visit on horseback or with a beautiful walk. A horse ride to the green lands of Montefeltro! Enjoy the wonderful views of the area on a horse ride along the itineraries proposed by us.

18–25 Feb

$99 NZD per night

Guest favourite

Farm stay in Ruscello, Italy

4.99 out of 5 average rating, 323 reviews

Agriturismo Fattoria La Parita

Provençal-style apartment nestled between the vineyard and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 from the highway. The singing of the acorn and cuckoo will be the soundtrack to the living room while the roe deer burn among the olive trees. It includes a basic Italian breakfast (coffee, tea, milk, cookies, etc.) that you can prepare on your own, if you want to try one of the famous breakfasts prepared and served by Sandra, the cost is €10 per person (6€ 5 to 15 years)

1–8 Sep

$266 NZD per night

Guest favourite

Villa in Castiglion Fiorentino, Italy

4.93 out of 5 average rating, 181 reviews

Tuscan charm of villa - countryside

Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

10–17 Mar

$710 NZD per night

Guest favourite

Home in Città di San Marino, San Marino

4.95 out of 5 average rating, 102 reviews

RESIDENCE RICCARDI deluxe *****

Appartamento in zona tranquilla a 10 minuti di camminata panoramica dal centro storico di San Marino il comprensorio offre parchi zone pedonali e campi da tennis in poco tempo si può raggiungere anche borgo maggiore tramite le gallerie del treno oggi adibite a zona perdonabile. Il comprensorio anche per escursioni in mtb. L'appartamento rustico con pavimenti in mattoni antichi e muri in pietra è stato da poco ristrutturato ed offre tutti i confort aria condizionata e riscaldamento autonomo.

25 Dec – 1 Jan

$205 NZD per night

Guest favourite

Tiny home in Anghiari, Italy

4.93 out of 5 average rating, 174 reviews

Anghiari. Living room in the room with a view

The small village of Tortigliano, 5 km from Anghiari, has medieval origins, surrounded by hills where Etruscans have put their roots for the first great Italian civilization. The yellow stones of the walls breathe among centuries-old cypress trees and the bell tower of a small church of the 600, you will be the only guests of an enchanted place. The village, abandoned after the war, was entirely recovered in its original system. Starting point to discover the taste of Tuscany at the table.

3–10 Oct

$153 NZD per night

Guest favourite

Condo in Teodorano , Italy

4.96 out of 5 average rating, 178 reviews

The ruin Teodorano, in the relaxing nature.

It is a typical Romagna farmhouse of the early 1900s, nestled in the Romagna hills between Forlì and Cesena. A few kilometers from the Romagna Riviera, you are immersed in the middle of the green and sunny hills where in addition to relaxing in the pool available(seasonal summer opening),you can practice several outdoor activities, including hiking, bike rides and much more. BBQ area and shaded area are available for guests to provide guests with a shaded area for outdoor dining.

27 Dec – 3 Jan

$151 NZD per night

Guest favourite

Tiny home in Novafeltria, Italy

5.0 out of 5 average rating, 64 reviews

A house with every comfort surrounded by greenery

Ideal house for those looking for privacy and relaxation. Just one!Well-kept environment equipped with every comfort . It hosts two people and a child up to 3 years old. An English bathtub in the master bedroom. Perfect home for bikers with bike garage. Outside there is a large, fully fenced garden and an exclusive patio where breakfast is served. BBQ grill available. Adjacent to the Marecchia River bike route from the garden. Ideal accommodation to explore Valmarecchia.

25 Apr – 2 May

$146 NZD per night

Guest favourite

Apartment in Montesoffio, Italy

5.0 out of 5 average rating, 172 reviews

A Casa di Adria

Newly renovated apartment, located 7 km from the center of Urbino, overlooking the Montefeltro countryside, ideal for those who want to spend a relaxing time walking in the greenery. The accommodation consists of a kitchen, living room and a bathroom on the ground floor, and a double bedroom, a bedroom with two single beds and a bathroom on the first floor. Also, a toddler bed is also available upon request. The apartment has a private entrance and parking.

9–16 Oct

$128 NZD per night

Guest favourite

Home in Città di San Marino, San Marino

5.0 out of 5 average rating, 91 reviews

B&B Balsimelli12

Entire ancient house, historic residence with two double bedrooms on two levels with internal staircase, one bedroom on the first floor with terrace and one on the ground floor, both with en-suite bathrooms. The beds are 160x200 cm. My accommodation offers splendid panoramic views, and is in the historical center close to all the monuments of the city. It is suitable for couples or families, solitary adventurers or business travellers. welcome pets.

13–20 Jan

$168 NZD per night

Guest favourite

Home in Anghiari, Italy

4.99 out of 5 average rating, 197 reviews

Casa Rosmarino Eco-Wellness Country Home

Price Includes: - WELLNESS HOT TUB w/Jacuzzi Infrared SAUNA - FOOD & DRINKS 1 Welcome Aperitivo 1 Wine 1 Nespresso w/Capsules - COMFORT Heater 2 Night Included, Extra Night 25 Euro Shower Gel / Shampoo / Hair Dryers Bathrobes / Flips Flops Wood for the HotTub and Fireplace - EXTRA (not included) MASSAGES PASTA Making Class, Oil/Truffle/Wine TASTING Please INQUIRE for price & availability

27 Feb – 6 Mar

$732 NZD per night

Guest favourite

Home in San Leo, Italy

5.0 out of 5 average rating, 13 reviews

Stone house of the 18th century in the historic centre

Enjoy a stylish experience at this centrally-located place. Step out of time to experience the exciting medieval village of San Leo. Wonderful apartment entirely in stone in a perfectly renovated eighteenth-century building just a few steps from the famous fortress and the cathedral. Large double bedroom, very comfortable double sofa bed, kitchenette and bathroom. You're just gonna want to come back.

13–20 Aug

$270 NZD per night