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Penna Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

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 HK$1,408
HK$1,549 total
includes taxes & fees
2 Sept - 3 Sept
Relais Villa Belpoggio - Residenza d'Epoca
Lobby

2. 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 HK$1,673
HK$1,840 total
includes taxes & fees
1 Sept - 2 Sept
Villa Cassia di Baccano
Private kitchen

3. 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 HK$503
HK$1,034 total
includes taxes & fees
23 Aug - 24 Aug
Cennano Suite - enter apartment
Pool

4. Borgo di Erboli

Borgo di Erboli
Cavriglia
The price is HK$865
HK$970 total
includes taxes & fees
21 Sept - 22 Sept
Borgo di Erboli
View from room

5. Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
9.8 out of 10, Exceptional, (7 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 HK$1,318
HK$1,477 total
includes taxes & fees
31 Aug - 1 Sept
Casa Vacanze Le Fornaci
Property grounds

6. LE BOTTI FIORENTINE

LE BOTTI FIORENTINE
Reggello
The price is HK$1,373
HK$1,556 total
includes taxes & fees
31 Aug - 1 Sept
LE BOTTI FIORENTINE
Outdoor pool

7. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (38 reviews)
"Great spot"
Canada
Philippe
The price is HK$1,269
HK$1,395 total
includes taxes & fees
21 Sept - 22 Sept
Villa di Sotto
Exterior

8. 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 HK$940
HK$1,034 total
includes taxes & fees
22 Aug - 23 Aug
Locanda Antico Borgo
Dining

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

Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Montevarchi
The price is HK$1,730
HK$2,645 total
includes taxes & fees
23 Aug - 24 Aug
Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Rooftop pool

10. 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 HK$873
HK$974 total
includes taxes & fees
20 Sept - 21 Sept
Relais Villa Belvedere
Exterior

11. 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 HK$1,193
HK$1,386 total
includes taxes & fees
23 Aug - 24 Aug
L' Eroico
Front of property

12. 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 HK$900
HK$990 total
includes taxes & fees
17 Sept - 18 Sept
Villa La Ginestra
Outdoor pool

13. Villa Il Palagio

Villa Il Palagio
Rignano sull'Arno
8.8 out of 10, Excellent, (77 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 HK$749
HK$860 total
includes taxes & fees
13 Sept - 14 Sept
Villa Il Palagio
Property entrance

14. 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 HK$999
HK$1,098 total
includes taxes & fees
22 Aug - 23 Aug
Palazzo Tarlati Residenza d'Epoca
Outdoor dining

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

Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
Figline Valdarno
The price is HK$577
HK$1,034 total
includes taxes & fees
22 Aug - 23 Aug
Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
Aerial view

16. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (73 reviews)
"Beautiful property"
Canada
Mary
The price is HK$1,425
HK$1,604 total
includes taxes & fees
20 Sept - 21 Sept
Villa Curina Resort
Interior

17. 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 HK$1,385
HK$1,897 total
includes taxes & fees
25 Aug - 26 Aug
Tuscany Family Getaway Near Florence | Parking + AC | Sleeps 8
Breakfast area

18. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
United States
Julia
The price is HK$2,497
HK$2,783 total
includes taxes & fees
24 Aug - 25 Aug
Terre di Baccio
Exterior

19. 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 HK$1,217
HK$1,412 total
includes taxes & fees
23 Aug - 24 Aug
Borgo Argenina
Outdoor dining

20. 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 HK$3,409
HK$3,803 total
includes taxes & fees
20 Sept - 21 Sept
Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
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

Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"Beautiful property. Quiet and well-maintained."
Paisley 2-night trip
Posted 6 hours ago
Castello Vicchiomaggio

Find out more about Penna

Search for holiday rentals in Penna on Expedia! You can easily find your home rentals, villas, holiday apartments in Penna using one of the methods below:

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Look no further and take a look at our great range of rental properties in Penna!

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.