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Penna Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Penna holiday rentals

Front of property

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 NZ$331
includes taxes & fees
2 Sept - 3 Sept
Relais Villa Belpoggio - Residenza d'Epoca
Interior

2. Little cozy house

Little cozy house
Loro Ciuffenna
The price is NZ$157
includes taxes & fees
7 Aug - 8 Aug
Little cozy house
Lobby

3. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (24 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is NZ$322
includes taxes & fees
6 Aug - 7 Aug
Villa Cassia di Baccano
Coffee/tea maker, fridge, microwave, oven

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$221
includes taxes & fees
6 Aug - 7 Aug
Cennano Suite - enter apartment
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

5. Borgo di Erboli

Borgo di Erboli
Cavriglia
The price is NZ$233
includes taxes & fees
9 Aug - 10 Aug
Borgo di Erboli
Exterior

6. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (328 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
The price is NZ$194
includes taxes & fees
11 Aug - 12 Aug
Hu Norcenni Girasole Village
Family Apartment, 2 Bedrooms, Hill View, Tower | View from room

7. Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
9.8 out of 10, Exceptional, (6 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 NZ$316
includes taxes & fees
1 Sept - 2 Sept
Casa Vacanze Le Fornaci
Property grounds

8. LE BOTTI FIORENTINE

LE BOTTI FIORENTINE
Reggello
The price is NZ$337
includes taxes & fees
1 Sept - 2 Sept
LE BOTTI FIORENTINE
Exterior

9. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (14 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 NZ$277
includes taxes & fees
8 Aug - 9 Aug
L' Eroico
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers

10. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (37 reviews)
"Great spot"
Canada
Philippe
The price is NZ$322
includes taxes & fees
10 Aug - 11 Aug
Villa di Sotto
Dining

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

Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Montevarchi
The price is NZ$566
includes taxes & fees
10 Aug - 11 Aug
Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas, pool loungers

12. Villa Il Palagio

Villa Il Palagio
Rignano sull'Arno
8.8 out of 10, Excellent, (74 reviews)
"Our family of five enjoyed our time at the property very much. The rooms were comfortable and the surrounding area is beautiful. The pool is a huge plus to cool down and have a relaxing time. The Rignano train station nearby makes it easy to get around Italy, by connecting to Florence’s main station. Truly an asset. The A1 highway is also nearby connecting you within easy access to beautiful Tuscany. Restaurants in the area were very good also. I would definitely stay again at Vila Il...
United States
Nuno
The price is NZ$182
includes taxes & fees
26 Aug - 27 Aug
Villa Il Palagio
Exterior detail

13. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.4 out of 10, Exceptional, (23 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 NZ$311
includes taxes & fees
7 Aug - 8 Aug
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Interior

14. Tuscany Family Getaway Near Florence | Parking + AC | Sleeps 8

Tuscany Family Getaway Near Florence | Parking + AC | Sleeps 8
Figline e Incisa Valdarno
The price is NZ$402
includes taxes & fees
6 Aug - 7 Aug
Tuscany Family Getaway Near Florence | Parking + AC | Sleeps 8
Property amenity

15. Camping Village Il Poggetto.

Camping Village Il Poggetto.
3.0 star property
Rignano sull'Arno
8.0 out of 10, Very good, (73 reviews)
"Nice property, very reasonable price"
United States
Alex
The price is NZ$123
includes taxes & fees
5 Sept - 6 Sept
Camping Village Il Poggetto.
Exterior

16. Villa Norcenni Aparthotel

Villa Norcenni Aparthotel
2.0 star property
Figline e Incisa Valdarno
7.4 out of 10, Good, (22 reviews)
"It was clean and safe."
United Kingdom
Laka
The price is NZ$173
includes taxes & fees
7 Aug - 8 Aug
Villa Norcenni Aparthotel
Exterior

17. 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$215
includes taxes & fees
5 Sept - 6 Sept
Locanda Antico Borgo
Exterior

18. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"A very peaceful and relaxing B&B that I highly recommend, spacious rooms , clean and well maintained! Host were very pleasing and helpful… definitely recommend!!"
Canada
Sabatino
The price is NZ$559
includes taxes & fees
17 Aug - 18 Aug
Borgo Argenina
Property entrance

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 NZ$235
includes taxes & fees
6 Aug - 7 Aug
Palazzo Tarlati Residenza d'Epoca
Aerial view

20. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (73 reviews)
"Beautiful property"
Canada
Mary
The price is NZ$315
includes taxes & fees
9 Aug - 10 Aug
Villa Curina Resort
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

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

10/10 Excellent
"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend."
Nicholas 7-night trip
Posted 9 hours ago
Borgo Scopeto Wine & Country Relais

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$123 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. 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.