Holiday Rentals Penna from £60: Find Short-Term Rentals & Holiday Accommodations

Q: What are some of the best holiday rentals that Penna has to offer?

Borgo Argiano : This holiday home rental outside of Penna is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. You can relax into your holiday with a garden and a library.

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Our top choices for Penna holiday rentals

Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

Mona

includes taxes & fees

29 Jul - 30 Jul

Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

includes taxes & fees

17 Aug - 18 Aug

Little cozy house

Loro Ciuffenna

includes taxes & fees

23 Jul - 24 Jul

Coffee/tea maker, fridge, microwave, oven

Cennano Suite - enter apartment

Montevarchi

Judith T.

includes taxes & fees

23 Jul - 24 Jul

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

Borgo di Erboli

Cavriglia

includes taxes & fees

1 Aug - 2 Aug

Frem SGV between Chianti Florence and Arezzo

San Giovanni Valdarno

"The property is of new and modern construction with all the amenities you would want. The grounds are landscaped, with beautiful trees and plants and the front deck is perfect for evening wine and snacks overlooking countryside hills in the distance. We would definitely stay here again while visiting this region of Tuscany. Centrally located to be able to reach northern and southern Tuscany by car or train."

John K.

includes taxes & fees

23 Jul - 24 Jul

Hu Norcenni Girasole Village

Figline e Incisa Valdarno

Kalinka

includes taxes & fees

24 Jul - 25 Jul

Room 'Ricasoli' with Wi-Fi

Montevarchi

includes taxes & fees

23 Jul - 24 Jul

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Top Penna Hotel Reviews

La Certosa di Pontignano

10/10 Excellent

"Everything was perfect!"

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"Borgo refers to something like little village and that’s what this property is. A cluster of beautiful stone buildings and gravel drives surrounded by acres of olive and lavender. Beautifully appointed common and areas in rooms. Excellent restaurant with elevated cuisine. Beautiful pool. Distance skyline view of Sienna, Really no negatives. Would definitely come back."

Hotel Le Fontanelle

10/10 Excellent

"The photos might hint at the quality of the property but don’t really do it justice. The sweeping easterly, vineyard views across to Monti-in-Chianti and up to Brolio are really mesmerizing. Grounds were well kept. Breakfast had the usual Italian selection of good fruits, grains, meats, breads, and sweets. Coupled with a limited menu of ala carte items and rich cappuccinos! Our suite was located about .25mi south of the main building. We enjoyed the walk multiple times per day but grandma might not. The room was nicely appointed with a living room, large bedroom, closet space and two sink bathroom. Stocked mini-fridge and cof/tea selections. Each room had its own outdoor area with a table/chaise to enjoy with coffee or after the pool. The out door pool is not heated (indoor pool is) but very comfortable on the 90 degree days we spent there. Pool service isn’t quite the same as some resorts, as you would go to the bar to order food/beverage and they’d bring it out to your chair setup. A good selection of menu items are available to choose from. Restaurants on site were excellent. Had the Bistecca at Tuscanio and it was perfection while LaColonna’s carpaccio and fusilli dish were both a treat. Staff was friendly though a bit harried. Seemed like they just needed a few more bodies around to smooth out the place. Ilaria at the front desk was really outstanding with her command and knowledge. While Marcella really made the pool with her wry smile and daily daiquiri selection."

Hotel Continentale

8/10 Good

"The most prominent feature of this hotel is the terrace, what a fabulous view! The staff were very helpful and friendly, showing the Gym which is slightly hidden away behind the bar and the large relaxing public lounge. There is a wide offer for breakfast in a large room which I think is underused. It would for instance be a great place for a reception or other formal gathering."

Dievole Wine Resort

10/10 Excellent

"Our stay at this Tuscan wine resort was nothing short of magical. Surrounded by stunning vineyards and ancient olive groves, the property is impeccably maintained and exudes refined, quiet elegance. The rooms and dining areas are spotless and sophisticated, providing the perfect backdrop for the truly elevated, delicious meals we enjoyed. The service was exceptional throughout, with a special thank you to Veronica and Gianluca, whose warmth and impeccable care made our experience unforgettable. This is the ultimate Tuscan escape— we cannot wait to return!"

Find out more about Penna

Everything you need to know about Penna 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 Penna holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Penna holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Penna holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Penna. 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 Penna 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 Penna holiday rentals we have selected for you start as low as £60 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Penna rentals

At Expedia, we put the best Penna 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 Penna 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 Penna 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 Penna. 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

Are there holiday rentals in Penna?

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

Borgo Argiano: This holiday home rental outside of Penna is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Penna?

Choose from 3 Expedia holiday rentals in Penna for a memorable holiday.

What can I see and do in Penna?

While exploring the area, visit family-friendly sights like Borgo di Vescine - Tenute di Castelvecchi, or get outside and enjoy nature at Piazza Guido Monaco. San Pietro a Gropina and Croce del Pratomagno are a couple of places you'll find in the wider area.

What are holiday rentals like in Penna?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Penna. Holiday rentals feature extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.

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Our top choices for Penna holiday rentals