
House holiday rentals in Castiglione dei Pepoli
Find and book unique houses on Airbnb
Top-rated house rentals in Castiglione dei Pepoli
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 Castiglione dei Pepoli
House rentals with a pool

Scenic country house with large pool near Florence
Absolute Perfection in Fiesole!** Michael’s villa in Fiesole is nothing short of spectacular. From the moment we arrived, we were mesmerized by the breathtaking views of the Tuscan countryside and Florence in the distance. The location is ideal—peaceful, romantic, and just a short drive from the heart of Florence, making it the perfect blend of serenity and convenience. The villa itself is stunning—spacious, elegantly decorated, and equipped with every amenity you could need. The outdoor terrace was our favorite spot, where we enjoyed morning coffee with panoramic views and evening wine under the stars. The lush gardens and private pool added an extra touch of luxury to our stay. Michael was an exceptional host—attentive, welcoming, and full of great local recommendations. His hospitality truly made our experience unforgettable. If you’re looking for a dreamy Tuscan escape with world-class scenery, impeccable style, and top-notch service, this is the place. We can’t wait to

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.

I Limoni Apartment in Tuscany
Incredible home, with stunning views! I hosted a group of friends here before my wedding, and we all agreed it was the most beautiful Airbnb we have ever stayed in. The hosts (Francesco and his wife Illaria) were extremely responsive and kind. They recommended a local chef to us, which turned into one of the best nights of our trip. 100% recommend and will be re-booking next time I travel to Tuscany.
Tuscan Villa Featured Conde Nast Best Villas Italy
This 500 year old house is ideally situated in Tuscany and the Chianti region. It is a perfect place for day trips to other towns, for wine, tasting excursions, and for visiting Florence. The idyllic setting gives you a sense of country life in Italy, and the views from the patio and house are stunning. There are spectacular wineries within 5 to 10 minutes of the house. We found the house very comfortable and enjoyed our stay very very much. Rose and Pier couldn’t have been more helpful in planning our stay and excursions. We found through them fabulous restaurants, and wineries that we would not have discovered on our own. They were also incredibly responsive when we had questions. Our only confusion about the house was that the listing showed three bathrooms, but one was in the laundry room in a separate building . Just something to know. Thank you to Rose for a lovely vacation ! It was the perfect place to explore Tuscany from!

Old barn The Nepitella
We had a very nice stay. We recommend this place.

[Villa San Jacopo Florence] Pool | Vineyards
We were a group of 10 staying Friday to Sunday at the villa. It is nestled in the beautiful Tuscan countryside. The rooms are spacious and the common areas perfect for a large group. It was very clean throughout. The kitchen is well designed and easy to use for a crowd. We deployed the large BBQ for a meal at home on the first evening. A cocktail, a steak and a view of the rolling hills - how charming! I would strongly recommend renting a car or cars because the village is some walk away. There is a large and well stocked Co-op about 10 minutes’ drive from the property. Giulia on behalf of the host was simply brilliant. She was very responsive and helpful, and full of good recommendations. I would not hesitate to endorse this property and its management - we had a brilliant stay and would happily come back again.

VILLA ORGANI 'the Daisy Cottage'
We had a wonderful stay. Everything was perfect. Carolina and her mother were most helpful and assisted when we had questions. We found the property so peaceful and beautiful. 10/10 stay. The breakfast was wonderful every morning. Thank you! Would recommend renting a car for this property!

Villa Laura
We had a wonderful stay at this villa! The house is super equipped for cooking, with everything you need available. The outdoor spaces are beautiful: lots of well-kept greenery, ideal for relaxing. The rooms are spacious and comfortable, and the area is very quiet, great for unwinding. The view is magnificent and the pool was perfect! Check-in was simple and communication with the host was impeccable: always available and friendly. Great value for money! Highly recommended
Weekly house rentals

Elegant ancient villa Lucca
From the moment we were greeted by Isabella, Massimo and their son, to the moment we said goodbye we felt right at home. The house is well located. It was nice to leave the hustle of the old city and retreat to the expansive peaceful terrace of the house for an “aperitivo” before dinner. The beds were comfortable and we all slept well after long days of touring. One of our favorite things was collecting water from the town spring, which was just a few doors away.

Montecatini Alto Art View
We loved staying in Carolina’s house in Montecatini Alto. It was a lovely welcoming place to wake up in and return to at the end of the day. The view from the windows and the patio is extraordinary and sitting out enjoying it was one of the best parts of the holiday. The house had all we needed. Carolina was a wonderful host; friendly, quick to reply and extremely helpful. The village is a lovely quiet place to stay and we wouldn’t look anywhere else if we return to the area.

Il Fienile, villa with garden
Due to a very complicated move I stayed alone at the property, unfortunately going back and forth to and from Bologna Working with animals and the garden, beautiful and fully fenced, it really made a difference The house is enchanting as well as the view that frames it, priceless to wake up to the view of our Apennines. So much silence to feel - especially at night - almost intimidated :-) Beautiful disconnect during which, at times, I was also able to regenerate I had some small difficulties with the TV in the room compared to the channel synchronization, while everything was fine with the one in the room Cleanliness and services offered completely in line with expectations Overall, I would absolutely recommend a stay at this charming structure if you really want to unplug and carve out a space and a moment of just relaxation and rest! Magician! Thank you for everything, Tiziana

La Loggia – Casine al Sole
Spontaneously booked. And can easily arrange everything necessary at short notice. Federico is calmly communicative and can refine the stay with good recommendations. The location is special. The place has a good effect on the body and mind. WeiläuAbout but not far for shopping or restaurants. A beautiful pool. Tasteful spaces. Wifi junckies could sometimes hate something with the net, but the overall picture is not diminished. Everything else necessary is on site or will be promptly provided by Federico. A wonderful starting point for Visit in Florence or Chianti. Lots of rustic trattorias,winemakers and olive farmers nearby.

Il Cerro Country House
Francesca warmly greeted us when we arrived at the house. She showed us around and helped out with any questions we had. The house itself is in a stunning location with beautiful views, we loved the place! It felt very homely and we had everything we needed inside. Would highly recommend!

Studio overlooking the river & garden
Lidia and her husband were perfect hosts! It felt right at home, we were warmly welcomed and they even gave us several rides, since we didn't have a car. Really kind and caring!

The Cannicciaia
Ignacio and Tamara went above and beyond in the warmth of their welcome and the dedication to their incredible home. An unforgettable experience!

Quadrifoglio House in Tuscany
We spent 6 days in a cozy, tastefully decorated place. Allessandra and Egizia were very welcoming and very concerned about our well-being. If we come back to this area, we'll be sure to get back in touch. Good compromise to visit Florence. beautiful Pistoia region.
Private house rentals

From Prato Porta Serraglio to Florence SMN Station
Many thanks to Patrizia for all the advice she provided during our stay. The apartment is very well located in the city center. We had a great time. Prato is a very pretty city and pleasant to visit. I would recommend this place without a second thought.

Casale Il Bramito
Nice house in the hills above Pistoia. It is a few degrees cooler than in the city, and you have a beautiful view. We enjoyed the chickens scratching around and the sweet cat. Also, in the evening, a lot of fireflies could be seen. Annalisa is very friendly and caring.

The Diospero
I am from California and stayed at 50 different Airbnb properties so far, mostly in the US, and most were very good, some were great, but none were like this property. this place is more than a place to stay. This was a very special and unique experience made possible by the great hospitality and generosity of the owners. I stayed for the entire Mugello MotoGP 2025 weekend and this location could not be more perfect to attend the race events every day. The views, the road to the property, the whole area and history or the area are all amazing. I got to learn a great deal about this beautiful part of the world and felt like I was an “Italian” for a few days. Highly recommended.

Villa Corte dello Zanchino, surrounded by greenery
Everything was great. The house is lovingly decorated and clean. The house has everything you need, the location is wonderful and close enough to Bologna. We can only recommend the house.

House in the Tuscan countryside
We really enjoyed our stay to explore the area. All major cities like Florence, Bologna, Lucca are in reach. Also good restaurants and the factory outlet in Barberino are in reach. Thank you for all the good advice.

Villa Porta Romana-Family CountryHouse in Florence
Our family of four loved this home. Here’s what felt extra luxurious to us: a separate wing for the 22 yr old, 3 bathrooms, high quality bed linen and towels, ability to do laundry and cook, wine and goodies on arrival, and a beautiful and serene park view. Birdsong in the morning, fireflies in the evening, pure magic.

Villa Vestra in Vinci holiday home
My husband and I had the great pleasure of spending 8 days at this beautiful Airbnb. Truly, this is the best Airbnb we've ever stayed in, and we travel a lot! With big intentions to explore the Tuscan area we essentially did nothing and stayed put. Why? It's just that beautiful. The view is spectacular, and the accommodations are very comfortable. The hosts have provided everything you need for a deep relaxing holiday. Of course if you choose to explore, there is much to see and do in the local area. We'll save all of our exploring for next time! Thank you Sylvia and Julio for a magic vacation.

Strozzi Square Amazing House
Fantastic place to stay! This was my second visit to this apartment because it’s in a perfect location, beautifully furnished, in a quiet neighborhood but five minutes from everything. The two bedrooms are very private and have a nice amount of space between them. Can’t recommend this more highly!
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
- Santa Maria Novella
- Duomo di Firenze
- Piazza del Duomo (Pisa)
- Stadio Renato Dall'Ara
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Basilica of Santa Maria Novella
- Mugello Circuit
- Ponte Vecchio
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Modena Golf & Country Club
- Giardino Bardini
- Lago di Isola Santa
- Medici Chapels
- The Boboli Gardens
- Pinocchio Park
- Teatro Verdi
- Nelson Mandela Forum