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Penna Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Penna holiday rentals

A rustic room with a stone wall, wooden furniture, and a breakfast buffet.

1. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (36 reviews)
"We had fantastic time here! The property is so beautiful and special! The views are stunning and the breakfast was very delicious! Hope we will come again! Special thanks to Tania who was very friendly and nice all the time!"
Germany
Kristina
The price is AU$256
includes taxes & fees
15 Nov - 16 Nov
Relais Villa Belpoggio - Residenza d'Epoca
A cozy living room with a stone wall, a fireplace, a bookshelf, and a coffee table with books.

2. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (27 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is AU$153
includes taxes & fees
15 Nov - 16 Nov
Villa Cassia di Baccano
An outdoor patio with brick flooring, tables, and chairs, surrounded by greenery and a view of a grassy landscape.

3. Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
9.8 out of 10, Exceptional, (7 reviews)
"Very nice hotel with friendly stad"
Denmark
Lisette
The price is AU$181
includes taxes & fees
22 Nov - 23 Nov
Casa Vacanze Le Fornaci
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

4. Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.0 out of 10, Wonderful, (77 reviews)
"True Tuscan style, beautiful views and a lovely breakfast."
Canada
Janet
The price is AU$167
includes taxes & fees
15 Nov - 16 Nov
Relais Villa Belvedere
A bedroom with a bed, bedside tables, a dresser, and wall art.

5. A cozy little house

A cozy little house
Loro Ciuffenna
The price is AU$134
includes taxes & fees
1 Dec - 2 Dec
A cozy little house
A stone building with a yellow sign reading "b&b erioico".

6. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
The price is AU$219
includes taxes & fees
22 Nov - 23 Nov
L' Eroico
An arched stone bridge with a white building on the right, featuring a balcony with plants.

7. Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (21 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 AU$159
includes taxes & fees
22 Nov - 23 Nov
Locanda Antico Borgo
Outdoor pool

8. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (45 reviews)
"It was wonderful!"
United States
Wade
The price is AU$144
includes taxes & fees
15 Nov - 16 Nov
iConic Wellness Resort
A modern living room with a television, a sliding glass door leading to a patio with outdoor furniture.

9. The Florence Hills Resort & Wellness

The Florence Hills Resort & Wellness
Pelago
8.8 out of 10, Excellent, (180 reviews)
"Enjoyed our stay and breakfast was great. "
Canada
Linda
The price is AU$112
includes taxes & fees
30 Nov - 1 Dec
The Florence Hills Resort & Wellness
A swimming pool with a curved edge, surrounded by a brick deck. In the background, there is a building with a tiled roof and a garden with various trees and shrubs.

10. 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$175
includes taxes & fees
16 Nov - 17 Nov
Villa La Ginestra
A wooden cabin with a curved roof, a wooden deck, and a gravel path leading to the entrance.

11. LE BOTTI FIORENTINE

LE BOTTI FIORENTINE
Reggello
The price is AU$260
includes taxes & fees
15 Nov - 16 Nov
LE BOTTI FIORENTINE
A poolside setting with two glasses of red drink, a tray with chips and olives, and a white umbrella.

12. Apartment in the Tuscan countryside with swimming pool.

Apartment in the Tuscan countryside with swimming pool.
Reggello FI
10.0 out of 10, Exceptional, (1 review)
The price is AU$185
includes taxes & fees
27 Nov - 28 Nov
Apartment in the Tuscan countryside with swimming pool.
A patio with a stone barbecue grill, a table with a black bowl, and a tree providing shade.

13. Holiday Home 'Il Piccolo Rifugio' with Pool, Garden and Wi-Fi

Holiday Home 'Il Piccolo Rifugio' with Pool, Garden and Wi-Fi
Figline Valdarno
The price is AU$184
includes taxes & fees
17 Nov - 18 Nov
Holiday Home 'Il Piccolo Rifugio' with Pool, Garden and Wi-Fi
A stone building with a covered patio, outdoor seating, and a gravel path.

14. Suite in a Tuscan farmhouse between Florence and Arezzo with Wi-Fi and a pool

Suite in a Tuscan farmhouse between Florence and Arezzo with Wi-Fi and a pool
Pian di Scò
The price is AU$190
includes taxes & fees
20 Nov - 21 Nov
Suite in a Tuscan farmhouse between Florence and Arezzo with Wi-Fi and a pool
A view from a window overlooking a rural landscape with a tall tree and distant hills.

15. A Pochi Passi dal Chianti, Immersi nel Verde con Animali Ammessi

A Pochi Passi dal Chianti, Immersi nel Verde con Animali Ammessi
Cavriglia
The price is AU$158
includes taxes & fees
1 Dec - 2 Dec
A Pochi Passi dal Chianti, Immersi nel Verde con Animali Ammessi
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

16. LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS

LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS
Ruffoli
9.2 out of 10, Wonderful, (28 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
The price is AU$248
includes taxes & fees
16 Nov - 17 Nov
LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS
A clear blue pool with lounge chairs and umbrellas, surrounded by trees and a hill in the background.

17. Relais Santa Margherita

Relais Santa Margherita
Capolona
8.0 out of 10, Very good, (6 reviews)
"Man entspannt gerne am Pool und der Bar."
Germany
Anonymous traveller
Relais Santa Margherita
A spa area with a stone-walled arch, a hot tub, and a small window.

18. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (31 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is AU$181
includes taxes & fees
22 Nov - 23 Nov
DormiVeglia B&B
A staircase with wooden steps and metal handrails, leading to an upper floor.

19. 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$274
includes taxes & fees
15 Nov - 16 Nov
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Property entrance

20. Palazzo Tarlati Residenza d'Epoca

Palazzo Tarlati Residenza d'Epoca
Civitella in Val di Chiana
8.0 out of 10, Very good, (3 reviews)
"Small family-owned inn located in center of Civitella in Val di Chiana. Room was comfortable and included all we needed. It was cold upon check-in which the co-owner tried to remedy with a space heater. It took a while. The room warmed up after the first night. The other co-owner kindly offered me our first night complimentary. (Thank you again.). The breakfast was simple and included fruit, juice, yogurt, sliced cheese and cold cut, packages sweets, tea, coffee and water. The owners were...
United States
Marco
The price is AU$260
includes taxes & fees
15 Nov - 16 Nov
Palazzo Tarlati Residenza d'Epoca
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

Il Borro - Relais & Châteaux

Il Borro - Relais & Châteaux

10/10 Excellent
"Excellent unique property with top notch service, attention and experiences. The food and staff at Osteria Il Borro were exceptional!"
Kelly 2-night trip
Posted 5 days ago
Il Borro - Relais & Châteaux

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$167 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 kitchenware. 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.