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Penna Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Penna holiday rentals

A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

1. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (35 reviews)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is AU$242
includes taxes & fees
30 Sept - 1 Oct
Relais Villa Belpoggio - Residenza d'Epoca
A cozy living room with a stone wall, a wine rack, and two sofas.

2. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (26 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is AU$268
includes taxes & fees
10 Oct - 11 Oct
Villa Cassia di Baccano
An outdoor patio with a wooden pergola, a sofa, a table, and chairs.

3. Blue villa surrounded by greenery between Arezzo Florence and Siena

Blue villa surrounded by greenery between Arezzo Florence and Siena
TERRANUOVA BRACCIOLINI
The price is AU$301
includes taxes & fees
1 Oct - 2 Oct
Blue villa surrounded by greenery between Arezzo Florence and Siena
A compact kitchen with a wooden countertop, stainless steel appliances, and a modern design.

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 AU$186
includes taxes & fees
29 Sept - 30 Sept
Cennano Suite - enter apartment
A wooden table with two chairs on a balcony, overlooking a lush green landscape with trees and hills.

5. 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$202
includes taxes & fees
5 Oct - 6 Oct
Casa Vacanze Le Fornaci
A pool area with a water slide and a stage for performances.

6. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (333 reviews)
"Amazing venue , lots of kids entertainment. Lots of facilities- shops restaurants. Splash parks were brilliant. Highly recommended."
United Kingdom
Katie
The price is AU$101
includes taxes & fees
29 Sept - 30 Sept
Hu Norcenni Girasole Village
A covered patio with a wooden table and chairs, stone walls, and a view of a garden.

7. Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (4 reviews)
"Pros: Guido og Angela var helt fantastiske værter og deres medhjælper sørgede godt for os med friske grøntsager fra haven. Poolen var perfekt og altid ren og pæn. For os var det helt perfekt vi kun var to familier og at der var ro Cons: Vi har ingen kritik punkter ☺️"
Denmark
Anonymous traveller
The price is AU$643
includes taxes & fees
29 Sept - 30 Sept
Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

8. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (44 reviews)
"Roberto, his wife and his staff were all round great. Very friendly helpful and great service. We were very happy to find this authentic castle/village to stay in Tuscany."
Canada
Iain
The price is AU$392
includes taxes & fees
29 Sept - 30 Sept
Castello di Gargonza
A dining area with a brick archway, wooden dining table, chairs, and a chandelier.

9. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Montevarchi
The price is AU$469
includes taxes & fees
29 Sept - 30 Sept
Holiday Home 'Poggio Loccano' with Private Garden and Balcony
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

10. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (39 reviews)
"Great spot"
Canada
Philippe
The price is AU$310
includes taxes & fees
1 Oct - 2 Oct
Villa di Sotto
A market with a sign reading "BAR IL POGGETTO MARKET".

11. Camping Village Il Poggetto.

Camping Village Il Poggetto.
3.0 star property
Rignano sull'Arno
8.0 out of 10, Very good, (79 reviews)
"Nice property, very reasonable price"
United States
Alex
The price is AU$91
includes taxes & fees
29 Oct - 30 Oct
Camping Village Il Poggetto.
A garden pathway leading to a stone building with a brick wall, a pergola, and a small brick structure in the background.

12. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (2 reviews)
"Upon arrival Guido had everything prepared for us. A bottle of his amazing wine that he makes along with 2 wine glasses we’re waiting on the farmhouse table. The home had 2 very comfortable bedrooms and a bathroom along with a living room and kitchen. Front porch overlooks the stunning Tuscany fields. The swimming pool was refreshing and everything was beyond perfect. This location was everything and more. The hosts were so helpful. I will come back her again..make sure to take time for the...
United States
Marianne H.
The price is AU$654
includes taxes & fees
5 Oct - 6 Oct
Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
A narrow stone-paved alleyway with buildings on either side, some with wooden shutters and potted plants.

13. Borgo dei Corsi - VERGAIO 6 Apartment

Borgo dei Corsi - VERGAIO 6 Apartment
Raggiolo
9.4 out of 10, Exceptional, (17 reviews)
"We had a fab family holiday in Raggiolo. Luca was very friendly and helpful .The local people were very welcoming. The accommodation was superb."
United Kingdom
Neil A.
Borgo dei Corsi - VERGAIO 6 Apartment
A wooden structure with a circular door, surrounded by a garden with string lights and a view of distant mountains.

14. LE BOTTI FIORENTINE

LE BOTTI FIORENTINE
Reggello
The price is AU$218
includes taxes & fees
27 Oct - 28 Oct
LE BOTTI FIORENTINE
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

15. Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (75 reviews)
"True Tuscan style, beautiful views and a lovely breakfast."
Canada
Janet
The price is AU$165
includes taxes & fees
17 Oct - 18 Oct
Relais Villa Belvedere
A pool area with a water slide and a stage for performances.

16. Villa Norcenni Aparthotel

Villa Norcenni Aparthotel
2.0 star property
Figline e Incisa Valdarno
7.4 out of 10, Good, (24 reviews)
"It was clean and safe."
United Kingdom
Laka
The price is AU$94
includes taxes & fees
30 Sept - 1 Oct
Villa Norcenni Aparthotel
A swimming pool with lounge chairs, a tiled deck, and surrounding trees.

17. Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Bucine
The price is AU$654
includes taxes & fees
10 Oct - 11 Oct
Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

18. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (80 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is AU$902
includes taxes & fees
30 Sept - 1 Oct
Terre di Baccio

19. 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$195
includes taxes & fees
29 Sept - 30 Sept
Palazzo Tarlati Residenza d'Epoca
An arched stone bridge with a white building on the right, featuring a balcony with plants.

20. 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 AU$169
includes taxes & fees
1 Oct - 2 Oct
Locanda Antico Borgo
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

Villa Le Barone

Villa Le Barone

10/10 Excellent
"Charming place in Tuscany! Everything was absolutely perfect. We highly suggest to dine at the villa, it was exceptional. Breakfast was delicious as well."
Tereza 2-night trip
Posted 12 hours ago
Villa Le Barone

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$91 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. Croce del Pratomagno and Fattoria La Vialla 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.