Penna Holiday Rentals

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Our top choices for Penna holiday rentals

Townhouse in Arezzo

THE MONNA LISA RESORT
9.2 out of 10, Wonderful, (9 reviews)
"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 MONNA LISA RESORT

Townhouse in Loro Ciuffenna

Villa Cassia di Baccano
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is NZ$334
includes taxes & fees
4 Feb - 5 Feb
Villa Cassia di Baccano

Townhouse in Barberino Tavarnelle

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

Townhouse in Monte San Savino

DormiVeglia B&B
10.0 out of 10, Exceptional, (27 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
DormiVeglia B&B

Townhouse in Greve in Chianti

Terre di Baccio
9.8 out of 10, Exceptional, (71 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
Terre di Baccio

Townhouse in Arezzo Centro Storico

B&B 52cento
8.0 out of 10, Very good, (73 reviews)
"Stayed in the top floor room with the terrace and seating area. Definitely a great decision. Arrezo was the starting point of our Tuscany tour and glad we spent an extra night and day. Great room super convenient to town and the train station. "
United States
Edward
The price is NZ$141
includes taxes & fees
4 Feb - 5 Feb
B&B 52cento

Townhouse in Arezzo Centro Storico

Allegra Toscana - Affittacamere Guest house
7.0 out of 10, Good, (16 reviews)
"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
The price is NZ$138
includes taxes & fees
8 Feb - 9 Feb
Allegra Toscana - Affittacamere Guest house

Holiday Home in Castiglion fibocchi

Casa Da Vinci for two
8.0 out of 10, Very good, (1 review)
"Sauber gemütlich, nette Atmosphäre Einrichtung ist ausreichend."
Germany
Perdita I.
The price is NZ$135
includes taxes & fees
2 Feb - 3 Feb
Casa Da Vinci for two

Holiday Home in Castellina in Chianti

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

Townhouse in Pratovecchio Stia

B&B da Ronald...a Pian del Papa
8.0 out of 10, Very good, (11 reviews)
"Venlig betjening Primitivt Ingen varmt vand Meget koldt værelse"
Denmark
Mikael
B&B da Ronald...a Pian del Papa

Townhouse in Gaiole in Chianti

L' Eroico
10.0 out of 10, Exceptional, (12 reviews)
"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
10.0 out of 10, Exceptional, (3 reviews)
"Pros: Tutto molto pulito, il proprietario si è rivelata una persona gentilissima e molto disponibile"
Italy
Anonymous traveller
The price is NZ$170
includes taxes & fees
2 Feb - 3 Feb
Apartment "La Finestra sul Fiume" with Private Terrace

Apartment in Arezzo Centro Storico

Living suite Verdeconiglio in the heart of Arezzo
10.0 out of 10, Exceptional, (1 review)
"It was a beautiful and quiet part of town and was very close to everything. The property manager spoke pretty good English which made everything much easier. It is a beautiful comforting and clean stay in the heart of Arezzo. Thank you. Era una zona bellissima e tranquilla della città, vicinissima a tutto. Il gestore parlava un ottimo inglese, il che ha reso tutto molto più semplice. È stato un soggiorno splendido, confortevole e pulito nel cuore di Arezzo. Grazie."
United States
Andrew T.
The price is NZ$177
includes taxes & fees
22 Feb - 23 Feb
Living suite Verdeconiglio in the heart of Arezzo

Aparthotel in Rapolano Terme

Podere La Chiusella
9.4 out of 10, Exceptional, (30 reviews)
"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

Aparthotel in Rapolano Terme

La Murata
9.0 out of 10, Wonderful, (11 reviews)
"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$267
includes taxes & fees
2 Feb - 3 Feb
La Murata

Apartment in San Giovanni Valdarno

Zero Point
8.0 out of 10, Very good, (3 reviews)
"Sehr freundliche Vermieter, hat alles super funktioniert."
Germany
Familie K.
The price is NZ$290
includes taxes & fees
1 Feb - 2 Feb
Zero Point

Townhouse in Subbiano

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

Aparthotel in Figline e Incisa Valdarno

Relais Villa Belvedere
9.2 out of 10, Wonderful, (70 reviews)
"Very nice place"
United States
Maria
Relais Villa Belvedere

Townhouse in Arezzo Centro Storico

Cameracaffè Centro
8.6 out of 10, Excellent, (179 reviews)
"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$165
includes taxes & fees
6 Feb - 7 Feb
Cameracaffè Centro

Apartment in Montevarchi

Cennano Suite - enter apartment
10.0 out of 10, Exceptional, (3 reviews)
"After and before the tourist rushes of Florence. I enjoyed a few very quiet and relaxing days in a beautiful and spacious place. "
Germany
Judith T.
The price is NZ$224
includes taxes & fees
26 Jan - 27 Jan
Cennano Suite - enter apartment
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 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 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.