Penna Holiday Rentals

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Our top choices for Penna holiday rentals

iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (36 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is NZ$177
includes taxes & fees
4 May - 5 May
iConic Wellness Resort

The Florence Hills Resort & Wellness

The Florence Hills Resort & Wellness
Pelago
8.8 out of 10, Excellent, (177 reviews)
"Enjoyed our stay and breakfast was great. "
Canada
Linda
The price is NZ$141
includes taxes & fees
27 Apr - 28 Apr
The Florence Hills Resort & Wellness

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is NZ$188
includes taxes & fees
30 Apr - 1 May
DormiVeglia B&B

Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is NZ$199
includes taxes & fees
25 May - 26 May
Mariani Bed & Breakfast

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

B&B da Ronald...a Pian del Papa
Pratovecchio Stia
8.0 out of 10, Very good, (11 reviews)
"Venlig betjening Primitivt Ingen varmt vand Meget koldt værelse"
Denmark
Mikael
The price is NZ$156
includes taxes & fees
1 May - 2 May
B&B da Ronald...a Pian del Papa

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (181 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$201
includes taxes & fees
16 May - 17 May
Cameracaffè Centro

Deluxe room Cartazucchero in the heart of Arezzo

Deluxe room Cartazucchero in the heart of Arezzo
Arezzo Centro Storico
10.0 out of 10, Exceptional, (2 reviews)
"From all the places we stayed during our 13-day trip to Italy, this was by far our favorite. Fabio was incredibly communicative and friendly right from the start, sending us clear instructions on how to get there. He greeted us at the door with such warmth that it truly felt like we were staying with family. The room was spotless, beautifully decorated, and generously stocked with water, cookies, pastries, and other treats. It had the comfort and attention to detail of a hotel, yet the warmth of...
United States
Hector
The price is NZ$184
includes taxes & fees
4 May - 5 May
Deluxe room Cartazucchero in the heart of Arezzo

Podere La Chiusella

Podere La Chiusella
Rapolano Terme
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
The price is NZ$212
includes taxes & fees
3 May - 4 May
Podere La Chiusella

Dolce Casa 2 Summary:

Dolce Casa 2 Summary:
Arezzo
The price is NZ$213
includes taxes & fees
28 Apr - 29 Apr
Dolce Casa 2 Summary:

Villa Cristina

Villa Cristina
Castellina in Chianti
7.8 out of 10, Good, (39 reviews)
"Arnaque absolue par rapport aux photos. Sdb salle moisi partout, wc jaune de calcaire. Aucune isolation phonique. Photos ne correspondent pas Chambre dans garage hauteur sous planfond nulle obligé de se baisser."
France
pascal
The price is NZ$178
includes taxes & fees
16 May - 17 May
Villa Cristina

Gallo Nero apartment 2/4 people close to the center of Greve in Chianti

Gallo Nero apartment 2/4 people close to the center of Greve in Chianti
Greve in Chianti
The price is NZ$293
includes taxes & fees
27 Apr - 28 Apr
Gallo Nero apartment 2/4 people close to the center of Greve in Chianti

Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
The price is NZ$304
includes taxes & fees
27 Apr - 28 Apr
Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Cennano Suite - enter apartment

Cennano Suite - enter apartment
Montevarchi
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$205
includes taxes & fees
27 Apr - 28 Apr
Cennano Suite - enter apartment

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is NZ$303
includes taxes & fees
18 May - 19 May
Villa Cassia di Baccano

Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (20 reviews)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
The price is NZ$218
includes taxes & fees
27 Apr - 28 Apr
Locanda Antico Borgo

B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.0 out of 10, Very good, (76 reviews)
"Exactly how it is described and very near the train station. Walkable distance to all the things to do around there. I really enjoyed my stay there. "
United States
Maria de Lourdes
The price is NZ$184
includes taxes & fees
4 May - 5 May
B&B 52cento

ALESSANDRO HOLIDAY HOUSE - Merlot house with mini-pool in the center of Greve

ALESSANDRO HOLIDAY HOUSE - Merlot house with mini-pool in the center of Greve
Greve in Chianti
The price is NZ$313
includes taxes & fees
27 Apr - 28 Apr
ALESSANDRO HOLIDAY HOUSE - Merlot house with mini-pool in the center of Greve

Camping Village Il Poggetto.

Camping Village Il Poggetto.
3.0 star property
Rignano sull'Arno
8.0 out of 10, Very good, (68 reviews)
"Pet friendly and clean"
United Kingdom
Nancy
The price is NZ$128
includes taxes & fees
27 Apr - 28 Apr
Camping Village Il Poggetto.

Allegra Toscana - Affittacamere Guest house

Allegra Toscana - Affittacamere Guest house
Arezzo Centro Storico
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$221
includes taxes & fees
27 Apr - 28 Apr
Allegra Toscana - Affittacamere Guest house

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (13 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
The price is NZ$311
includes taxes & fees
27 Apr - 28 Apr
L' Eroico
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$128 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 espresso 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.