Penna Holiday Rentals

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Our top choices for Penna holiday rentals

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 AU$247
includes taxes & fees
28 Apr - 29 Apr
Villa Cassia di Baccano

Villa La Ginestra

Villa La Ginestra
Subbiano
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
The price is AU$211
includes taxes & fees
29 Mar - 30 Mar
Villa La Ginestra

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
The price is AU$377
includes taxes & fees
4 Apr - 5 Apr
Castello di Gargonza

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (22 reviews)
"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "
United States
Massimo
The price is AU$293
includes taxes & fees
31 Mar - 1 Apr
Borgo Argenina

Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
9.8 out of 10, Exceptional, (10 reviews)
"Great food in the area. Beautiful church tour and a fantastic host for our stay!"
United States
Craig & Conny M.
The price is AU$317
includes taxes & fees
30 Mar - 31 Mar
Chianti Craft House Badia a Passignano

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 AU$266
includes taxes & fees
31 Mar - 1 Apr
L' Eroico

La Vigna by Interhome

La Vigna by Interhome
Greve in Chianti
The price is AU$425
includes taxes & fees
9 Apr - 10 Apr
La Vigna by Interhome

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 AU$174
includes taxes & fees
17 Apr - 18 Apr
Mariani Bed & Breakfast

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (28 reviews)
"Lovely relaxation options and wonderful restaurant attached to the property! Great for a stay where you are travelling through Tuscany by car! Do not recommend travelling by public transport or taxi as it is very expensive."
Australia
Amelia
The price is AU$251
includes taxes & fees
29 Mar - 30 Mar
Villa di Sotto

Dolce Casa 2 Summary:

Dolce Casa 2 Summary:
Arezzo
The price is AU$179
includes taxes & fees
30 Mar - 31 Mar
Dolce Casa 2 Summary:

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 AU$132
includes taxes & fees
19 Apr - 20 Apr
iConic Wellness Resort

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
The price is AU$921
includes taxes & fees
29 Mar - 30 Mar
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (64 reviews)
"Great stay but can feel a bit captive to their restaurant for dinner. Min 2 courses mandatory per person and dessert doesn’t count "
Canada
Shelley
The price is AU$285
includes taxes & fees
1 Apr - 2 Apr
Villa Curina Resort

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (27 reviews)
"La habitación era preciosa, el desayuno riquísimo con muchas tartas y bizcochos caseros, Simona una anfitriona estupenda."
Spain
arturo
The price is AU$167
includes taxes & fees
29 Mar - 30 Mar
DormiVeglia B&B

Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
9.4 out of 10, Exceptional, (3 reviews)
"We absolutely loved our stay at this hotel. The suite was perfect and the restaurant had probably the best food I have had in Tuscany. We definitely plan to stay there again."
United States
Gregory
The price is AU$208
includes taxes & fees
29 Mar - 30 Mar
Casa Vacanze Le Fornaci

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 AU$145
includes taxes & fees
30 Mar - 31 Mar
Deluxe room Cartazucchero in the heart of Arezzo

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 AU$255
includes taxes & fees
9 Apr - 10 Apr
Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Taverna by Interhome

Taverna by Interhome
Greve in Chianti
The price is AU$633
includes taxes & fees
29 Mar - 30 Mar
Taverna by Interhome

Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
8.8 out of 10, Excellent, (3 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is AU$216
includes taxes & fees
29 Mar - 30 Mar
Casa Vacanze Squarcialupi

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (72 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is AU$715
includes taxes & fees
2 Apr - 3 Apr
Terre di Baccio
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 favourite 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 depend 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 AU$99 per night. Entering your travel dates in the search wizard might find you 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. Croce del Pratomagno and Franciscan Monastery of St. Francis 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.