Penna Holiday Rentals

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Holiday Rentals in Penna

Villa Cassia di Baccano

Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is NZ$268
includes taxes & fees
9 Dec - 10 Dec
Villa Cassia di Baccano

DormiVeglia B&B

Monte San Savino
10.0 out of 10, Exceptional, (27)
"This was our favourite B&B. The owner Simona was absolutely wonderful. The hot tub in our room was out of this world. If you have the chance to visite this gem…DO IT!!"
Canada
Claude
DormiVeglia B&B

THE MONNA LISA RESORT

Arezzo
9.6 out of 10, Exceptional, (8)
"Massimiliano was a great host, but we were the only guests and the restaurant was closed. The hotel was basically unmanaged. It should not have been listed as a hotel. "
United States
Bart
The price is NZ$248
includes taxes & fees
19 Dec - 20 Dec
THE MONNA LISA RESORT

La Locanda di Pietracupa

Barberino Tavarnelle
9.4 out of 10, Exceptional, (35)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa

Cameracaffè Centro

Arezzo Centro Storico
8.6 out of 10, Excellent, (179)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
The price is NZ$167
includes taxes & fees
15 Dec - 16 Dec
Cameracaffè Centro

L' Eroico

Gaiole in Chianti
10.0 out of 10, Exceptional, (12)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
L' Eroico

Terre di Baccio

Greve in Chianti
9.8 out of 10, Exceptional, (71)
"Great hotel in a beautiful location with fantastic staff. "
United Kingdom
Mark
Terre di Baccio

Relais Villa Belvedere

Figline e Incisa Valdarno
9.0 out of 10, Wonderful, (71)
"Very nice place"
United States
Maria
The price is NZ$185
includes taxes & fees
14 Dec - 15 Dec
Relais Villa Belvedere

Podere La Chiusella

Rapolano Terme
9.4 out of 10, Exceptional, (30)
"Et sjarmerende lite B&B. Har nok vært utrolig vakkert i sine glansdager, men områdene rundt bærer preg av lite vedlikehold. Leiligheten var helt grei for en overnatting. Gulvet på badet var ikke rent. Når vi tørket opp etter oss ble håndkleet møkkete. Men overnattingen var helt grei alt i alt. Når vi skulle sjekke ut var det ikke et menneske å se, resepsjonen var stengt. Endte med å sette nøklene i døra og dra da alt var betalt ved bestilling."
Norway
Elisabeth
Podere La Chiusella

Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna
9.8 out of 10, Exceptional, (35)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is NZ$312
includes taxes & fees
9 Dec - 10 Dec
Relais Villa Belpoggio - Residenza d'Epoca

The Florence Hills Resort & Wellness

Pelago
8.8 out of 10, Excellent, (175)
"Great stay would recommend "
United Kingdom
Luan
The Florence Hills Resort & Wellness

B&B da Ronald...a Pian del Papa

Pratovecchio Stia
8.0 out of 10, Very good, (11)
"La struttura è facilmente raggiungibile. Supersilenziosa e in una zona tranquilla, con un fantastico panorama. Proprietari gentilissimi!"
Italy
Tatiana
B&B da Ronald...a Pian del Papa

Allegra Toscana - Affittacamere Guest house

Arezzo Centro Storico
7.0 out of 10, Good, (16)
"Great location in Arezzo, easy and simple to find and access. Everything was exactly as we needed although we did not need to stay long."
United Kingdom
Justin
Allegra Toscana - Affittacamere Guest house

Castello di Gargonza

3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (39)
"All of the hotel staff did an outstanding job. Our room had everything we needed and the restaurant was great. Breakfast was exceptional. Special shoutout to Neri, the owner, for taking such good care of us. "
United States
Diane
Castello di Gargonza

Villa La Ginestra

Subbiano
9.6 out of 10, Exceptional, (5)
"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."
Canada
Philippe
Villa La Ginestra

Residenzia del Sogno

Castellina in Chianti
9.8 out of 10, Exceptional, (14)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is NZ$270
includes taxes & fees
2 Jan - 3 Jan 2026
Residenzia del Sogno

Antella Residence

Bagno a Ripoli
8.8 out of 10, Excellent, (6)
"Appartamento grande e pulito. Comodo. Fornito di ogni confort. La titolare è gentile e disponibile (al checkout però abbiamo provato a chiamarla per consegnare le chiavi ma non ha risposto nessuno è abbiamo dovuto lasciarle sul bancone della reception chiusa). Struttura silenziosa. Un po' di rumore dalla caldaia e dai termosifoni ma niente di insopportabile. La mattina abbiamo sentito un po' di rumori dovuti ad altri ospiti poco civili. Ad ogni modo, è un ottimo posto per alloggiare e girare nei...
Italy
Nunzia
The price is NZ$254
includes taxes & fees
9 Dec - 10 Dec
Antella Residence

La Murata

Rapolano Terme
9.0 out of 10, Wonderful, (11)
"Amazingly beautiful place! Wish i could have stayed longer to enjoy the view but was just passing through. The apartment was so cute and clean. Any family would enjoy staying here. I would stay here again if i were in the area."
United States
Elizabeth
The price is NZ$271
includes taxes & fees
8 Jan - 9 Jan 2026
La Murata

Agriturismo La Ferrozzola

Castellina in Chianti
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola

Rocca di Castagnoli

Gaiole in Chianti
9.2 out of 10, Wonderful, (28)
"It was wonderful to stay in a castle in Tuscany no less Every person we met was attentive and kind We were staying near friends and didn’t hang around the grounds much or use the pool but everything seemed well kept It’s really a place to retreat to eat at and sleep at which served our purpose well "
Canada
Shingo
The price is NZ$470
includes taxes & fees
1 Jan - 2 Jan 2026
Rocca di Castagnoli
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 Penna Hotel Reviews

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, 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 NZ$185 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 a coffee maker. 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. Mulino Ad Acqua 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.