Penna Vacation Rentals from ￥11,475: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Penna?

Borgo Argiano : Visitors like this Penna vacation home rental. It is located on a river and has a balcony, a terrace, and a barbecue grill 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 vacation with a garden and a library.

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In two weeks

In two months

In three months

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Our top choices for Penna vacation rentals

1. Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

Mona

￥34,408 total

includes taxes & fees

Aug 27 - Aug 28

2. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

￥35,024 total

includes taxes & fees

Sep 15 - Sep 16

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

3. Borgo di Erboli

Cavriglia

￥22,191 total

includes taxes & fees

Aug 18 - Aug 19

Family Apartment, 2 Bedrooms, Hill View, Tower | View from room

4. Casa Vacanze Le Fornaci

Pergine Valdarno

Gregory

￥29,751 total

includes taxes & fees

Aug 31 - Sep 1

5. Villa Norcenni Aparthotel

Figline e Incisa Valdarno

Laka

￥18,315 total

includes taxes & fees

Aug 16 - Aug 17

Coffee/tea maker, fridge, microwave, oven

6. Cennano Suite - enter apartment

Montevarchi

Judith T.

￥20,780 total

includes taxes & fees

Aug 16 - Aug 17

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

Montevarchi

￥53,144 total

includes taxes & fees

Aug 16 - Aug 17

8. LE BOTTI FIORENTINE

Reggello

￥31,673 total

includes taxes & fees

Sep 1 - Sep 2

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

9. Villa di Sotto

Castelnuovo Berardenga

Philippe

￥28,070 total

includes taxes & fees

Sep 10 - Sep 11

Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

10. Relais Villa Belvedere

Figline e Incisa Valdarno

Janet

￥22,930 total

includes taxes & fees

Sep 9 - Sep 10

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

Figline e Incisa Valdarno

￥37,937 total

includes taxes & fees

Aug 27 - Aug 28

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

Figline Valdarno

￥19,953 total

includes taxes & fees

Aug 16 - Aug 17

13. L' Eroico

Gaiole in Chianti

Angela

￥27,837 total

includes taxes & fees

Aug 24 - Aug 25

14. Palazzo Tarlati Residenza d'Epoca

Civitella in Val di Chiana

"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...

Marco

￥22,067 total

includes taxes & fees

Aug 18 - Aug 19

15. Hu Norcenni Girasole Village

Figline e Incisa Valdarno

Kalinka

￥17,368 total

includes taxes & fees

Aug 16 - Aug 17

16. Locanda Antico Borgo

Civitella in Val di Chiana

"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. "

Mr Andy

￥19,534 total

includes taxes & fees

Aug 16 - Aug 17

17. Villa Curina Resort

Castelnuovo Berardenga

Mary

￥32,182 total

includes taxes & fees

Aug 23 - Aug 24

18. Terre di Baccio

Greve in Chianti

"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!"

Julia

￥54,325 total

includes taxes & fees

Aug 17 - Aug 18

19. Castello di Gargonza

Monte San Savino

Ariel

￥44,410 total

includes taxes & fees

Aug 16 - Aug 17

Outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas, sun loungers

20. Villa Il Palagio

Rignano sull'Arno

"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...

Nuno

￥17,030 total

includes taxes & fees

Aug 31 - Sep 1

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Top Penna Hotel Reviews

Hotel Fattoria degli Usignoli

10/10 Excellent

"Gorgeous place, amazing views. They overbooked dinner and we had a wait of 2 hours for our food to come out. Pool was amazing and there was two to choose from, one looked quieter. Main part of the building is 15th century, which was beautiful. Easy to find with google maps NOT Apple Maps. Plenty of parking."

Villa Casagrande Resort & SPA

10/10 Excellent

"What a wonderful 3 night break at Villa Casagrande! My wife and I had a beautiful stay in this historic villa. There’s a little steep walk up to the pool and restaurant next to it which were perfect and where we spent most of our time relaxing and sunbathing with the view of the trees and the Tuscan mountains. The staff were incredible, so kind, quick to help and made our stay even more pleasant. We both had lovely massages and relaxed in the spa area and one evening did the historic tour and wine tasting which was exceptional. The guides and sommeliers were so knowledgeable and so lovely and the organic Chianti wines they produce are an absolute must to taste and buy. The hotel’s main restaurant was the best in Filigne (the local town) and the food was incredible. One of the nights we had a live musician who was fantastic. We had dinner twice there; mushroom tagliatelle, the lamb, the wild boar gnocchi and paccheri carbonara were to die for! It’s only 50 mins on the train to Florence which is one of our favourite cities to explore in one day and we picked this place especially because it’s only a 12 minute walk from the Filigne Valdarno station and avoids the need to hire a car. We went for the comfort room which was spacious and clean and the air con was great and important for us it had a powerful shower. We truly had a wonderful time and absolutely cannot wait to go back next year! Grazie Villa Casagrande!"

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."

Hotel Continentale

8/10 Good

"The most prominent feature of this hotel is the terrace, what a fabulous view! The staff were very helpful and friendly, showing the Gym which is slightly hidden away behind the bar and the large relaxing public lounge. There is a wide offer for breakfast in a large room which I think is underused. It would for instance be a great place for a reception or other formal gathering."

Find out more about Penna

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Frequently asked questions

Are there vacation rentals in Penna?

Yes, we offer vacation rentals near the most popular local attractions in Penna, or you can choose a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Penna?

Borgo Argiano: Visitors like this Penna vacation home rental. It is located on a river and has a balcony, a terrace, and a barbecue grill 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 vacation with a garden and a library.

How many vacation rentals are there in Penna?

Choose from 3 Expedia vacation rentals in Penna for a memorable vacation.

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 larger area.

What are vacation rentals like in Penna?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Penna. Vacation rentals feature extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.

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Check prices for these dates

Our top choices for Penna vacation rentals

1. Relais Villa Belpoggio - Residenza d'Epoca

2. Villa Cassia di Baccano

3. Borgo di Erboli

4. Casa Vacanze Le Fornaci

5. Villa Norcenni Aparthotel

6. Cennano Suite - enter apartment

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

8. LE BOTTI FIORENTINE

9. Villa di Sotto

10. Relais Villa Belvedere

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

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

13. L' Eroico

14. Palazzo Tarlati Residenza d'Epoca

15. Hu Norcenni Girasole Village

16. Locanda Antico Borgo

17. Villa Curina Resort

18. Terre di Baccio

19. Castello di Gargonza

20. Villa Il Palagio

Find vacation rentals that suit your style

Top Penna Hotel Reviews

Hotel Fattoria degli Usignoli

Villa Casagrande Resort & SPA

Hotel Villa Campomaggio

Belvedere di San Leonino

Hu Norcenni Girasole Village

Borgo Scopeto Wine & Country Relais

Castello di Spaltenna- Small Luxury Hotels of the World

La Certosa di Pontignano

Hotel Continentale

Find out more about Penna

Frequently asked questions

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