
House holiday rentals in Pennabilli
Find and book unique houses on Airbnb
Top-rated house rentals in Pennabilli
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Pennabilli
House rentals with a pool

Villa Podere Cerretino
Fabulous place in amazing surroundings. The pool area is wonderful and the garden beautiful. We had an amazing time and enjoyed the entire place - especially the outdoor pizza oven. Nicola was very helpful and fast in his responses.

Loggetta: farmhouse with garden and pool
We greatly enjoyed our stay at this beautiful home in Tuscany. The location is truly idyllic – quietly located on the top of a hill, overlooking the beautiful Tuscan landscape. The house fully met our expectations: comfortable, tidy and with everything we needed for a relaxing holiday. Upon arrival we were warmly welcomed by Giovanna, who immediately put us at ease. She took plenty of time to welcome us and also gave us valuable tips for visiting Arezzo and the surrounding area. In short: a wonderful place for those looking for peace, nature and authentic Tuscan charm. We'd love to come back!

Colonial house immersed in a natural park.
We spent two weeks at Rolando and Patrizia's with our two one-year-old and three-year-old children. The place is absolutely beautiful with a sublime view. They had a lot of little touches for our children throughout the stay. It was always a pleasure to chat with them. Accommodating, very considerate. The kids were always happy to see them. As for the house, it is very nice and easy to live in. The two terraces are a real plus. And again the views filled us throughout our stay.

Podere Bocci residence in Casentino - Entire Villa
We spent a few days ( 2-8.06.2025) at Podere Bocci with our family, and it was an absolutely exceptional time. The villa is even more beautiful than in the photos – very clean, spacious, and with a wonderful view of the Tuscan hills. The pool was perfect, discreetly cleaned every morning by the owner – everything was cared for down to the smallest detail. What impressed us the most, however, was the hospitality of the hosts – incredibly kind, helpful, and warm. They answered every question, brought us cake and prosecco for Grzesiek’s birthday, and surprised us with a delicious aperitivo at the end of our stay. We had never experienced such a warm welcome before – we truly felt exceptionally well taken care of. We wholeheartedly recommend this place to anyone looking for peace, the charm of Tuscany, and genuine kindness. We will definitely be back! Luciana, ti mandiamo un caro saluto e ti auguriamo tanta salute e ospiti simpatici! Monia&Greg and family

Il Monte
Great stay in beautiful house in beautiful house.

Il Casone - Country house with pool & wide garden
My friends & I spent 5 days at Il Casone in May, and what a delight it was. The Villa is both isolated and a short drive to various levels of towns and shops, cafes, and restaurants as needed. And of course a well equipped kitchen to cater for yourself. We were met by Roberta, the hosts father, and had a wonderful introduction and tour of the garden, the history and stories of the house and area, eventually we were allowed inside! It was a great welcome and Roberto was a good help to us many times we had questions the Villa is nicely renovated, farmhouse style and has everything you need it is very clean and good for people, like me, who might have mobility issues as it is all on one level and has wall in showers. While there we did a full day tour of the Chianti region which was great. They picked us up at the Villa and we visited two places to taste and also had lunch - do this! We loved our rural Idyll and would recommend Matteo’s Villa enthusiastically! Thanks Matteo & Robert

Casa dei Vasi
Our stay in Tuscany at Lorenzo’s estate was magical! Close to the gorgeous Anghiari, fresh pastry gifts from Lorenzo’s lovely mother every other day and magical firefly displays at night, the pool and wood fired hot tub were an especially nice touch, recommend and would stay again :)

Calbertone family and bike holidays Urbino
We stayed in 13 at Angelo's house, for the weekend of June 2. The house is very nice, in a quiet area, it is very spacious both inside and outside, with a patio and a garden that offer a beautiful view. The pool, being above ground, is not very large but absolutely functional for cooling off while enjoying the garden, and was very much used by the 5 girls of the group who had a great time! Angelo was always available and kind to us, a great host!
Weekly house rentals

welcome ca' ad scarplen
Excellent stay, Vanessa is a very kind, welcoming and warm person. She even made the effort to answer our questions in French. The house is very beautiful, well located, well-equipped, tastefully decorated, very pleasant to stay in. Rental advised friends for a pleasant stay. No unpleasant comments to be made.

The small tower
Franco is very welcoming, the apartment is a beautiful renovation equipped with every comfort. Highly recommended! Luca and Noélie

Terrace overlooking the park (La Legnaia)
Delightful people. Incredibly kind and helpful. I'm so pleased I chose to stay with Mauro. Very accomodating.

historical townhome in Poppi
This is hands-down the best AirBnB in the best little town in Italy. It’s the first time I’ve ever driven into a literal castle to park my car. Hopefully it won’t be my last. Joana was incredibly kind, responsive, and helpful. And she gave very clear instructions for arriving at and entering her apartment—not an easy feat in Italy. My favorite part of my stay was opening my windows in the morning and being greeted by an adorable nonna in the apartment across the street—“Buongiorno!” If you’re looking for a bona fide, non-touristy Italy experience, this is the spot for you.

Casa Il Melograno in the Romagna hills
We were in Mondaino for the Misono World Championship, we had a great time with the house, clean, efficient and with a magnificent view. I congratulate the hosts for their help and quick answers to our questions. We hope to be back soon! Highly recommended ☺️

The little house on the garden
A quiet neighborhood with wonderful hosts who make you feel at home from day one. A perfect place for real relaxation. Our dog appreciated the daily company of sweet Memole in the garden. Clean, comfortable, the surroundings of the house are a feast for the senses!Matteo, Marusca and Eva were very friendly and helpful in every matter. I hope we will strengthen this contact in the future!Highly recommended! Monika and Bernd

Oleandro, cozy studio in Val di Nima
Nicola bnb was amazing! Perfect to relax and such a lovely bnb. Nicola is the perfect host. Highly recommend. So very beautiful with surrounding huge mountains. A great base to explore surrounding areas. And a bonus, the cats are geougous. Thank you

Casa Carla
The experience in Carla's villa is by far the best I've ever had with Airbnb. The house is close to other villas but with a large well-kept garden of roses and medicinal plants and with deck chairs in which to spend moments of absolute calm. Carla waited for us in person to offer us a very welcome tart and explain every detail of the apartment, equipped with TV, wifi and all the kitchen equipment (very, very nice), including a kettle, coffee machine and pods and a nice and welcoming decor. The bed is the best on Airbnb. Absolute peace. The only regret: we only stayed two nights.
Private house rentals

"Tuscany Villa with PRIVATE pool"
We had a fantastic week The house is nice and well equipped The pool is so nice, big and clean We can strongly recommend this house to others.

Casa Guardiano - Tuscan countryside house
Such great accommodation on a lovely farm. Very well kept gardens and an excellent pool. The hosts are very friendly and will make you feel at home

Sant'Eufemia 13 - Farmhouse 4 km from Urbino
Beautiful, peaceful location A few minutes from Urbino Well equiped kitchen A place where you can cook, relax and get away from everything. Highly recommended

Tuscan Rustic
We loved our stay, the villa is beautifully done, has all of the amenities needed, was spotlessly clean and our hosts were so welcoming and provided lots of recommendations on places to visit and even made us a delicious pizza and shared a local wine. The view from the villa is breathtaking, watching the clouds roll through in the distance every morning whilst eating breakfast was amazing. Highly recommend.

La Fonte Casentino Guest House
We had a great time in the middle of nature, tranquility, clean air and with a great view. Eleonora was always kind and helpful, very warm welcome.

[PORTO CANALE] MODERN APARTMENT IN THE CENTER
Outstanding cosy apartment, really nice, right on the Porto canale - outstanding location. No kitchen, but you would be crazy cooling at home with such great restaurants around ! Valerio recommended the perfect parking spot. Always reactive. A lady living right in front of the apartment helps him out, she also provided some excellent local recommendations. Outstanding experience, we will be back !

Casa Ciappi
We loved staying at Michela's place! It is situated in such a beautiful and peaceful area. Michela was very accommodating and friendly. The family set up a tramp at the end for my kid's, and they absolutely loved it. They had some fun toys we played with as well. The home is pretty far from any main sites, and we drove a little more than we were planning, but if you're looking for a beautiful retreat away from it all, this is the place!

La Bella Signora Holiday Home
The place was absolutely perfect for us, a beautiful house and a house with soul. Very nice terrace (very nice with the small pool on hot days) and garden, cozy living rooms. We felt at home from the first day. The house is located in a nice old town, with a short distance to many beautiful Italian cities, and to many good restaurants, but you are completely dependent on a car. We also found great opportunities for hiking. Manuela and Massimo were very helpful and nice, gave us daily tips on things to do and places to visit, and were very flexible when we had visitors from Norway. Manuela came by with cakes and wine, and had made delicious food for us when we arrived, since all the shops were closed at Easter. We enjoyed Laterina and the house very much, and we will be happy to return.
Destinations to explore
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Lake Trasimeno
- Fiera Di Rimini
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Malatestiano Temple
- Mirabilandia
- Misano World Circuit
- Frasassi Caves
- Miramare Beach
- Italia in Miniatura
- Palacongressi Della Riviera Di Rimini
- Riminiterme
- Stadio Artemio Franchi
- Avignonesi Winery Fattoria Le Capezzine
- Oltremare
- Papeete Beach
- Teatro Tuscanyhall
- Basilica di Sant'Apollinare in Classe
- Nelson Mandela Forum
- Portoverde
- Villa delle Rose
- Fiabilandia
- Chiesa San Giuliano Martire
- Bagno Egisto