Holiday Rentals Penna from ฿2,215: Find Short-Term Rentals & Holiday Accommodations

Q: 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.

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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

Loro Ciuffenna

Kristina

฿5,938 total

includes taxes & fees

6 Dec - 7 Dec

A cozy living room with a stone wall, a fireplace, a bookshelf, and a coffee table with books.

2. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

฿3,520 total

includes taxes & fees

15 Nov - 16 Nov

An outdoor patio with brick flooring, tables, and chairs, surrounded by greenery and a view of a grassy landscape.

3. Casa Vacanze Le Fornaci

Pergine Valdarno

Lisette

฿4,423 total

includes taxes & fees

15 Nov - 16 Nov

A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

4. Relais Villa Belvedere

Figline e Incisa Valdarno

Janet

฿4,035 total

includes taxes & fees

9 Dec - 10 Dec

A stone building with a yellow sign reading "b&b erioico".

5. L' Eroico

Gaiole in Chianti

Angela

฿5,042 total

includes taxes & fees

15 Nov - 16 Nov

An arched stone bridge with a white building on the right, featuring a balcony with plants.

6. 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

฿4,304 total

includes taxes & fees

16 Nov - 17 Nov

7. iConic Wellness Resort

Arezzo

Wade

฿3,323 total

includes taxes & fees

15 Nov - 16 Nov

A modern living room with a television, a sliding glass door leading to a patio with outdoor furniture.

8. The Florence Hills Resort & Wellness

Pelago

Linda

฿2,587 total

includes taxes & fees

30 Nov - 1 Dec

A bedroom with a patterned wall, a wooden headboard, a bedside table with a lamp, and a patterned rug.

9. Villa La Ginestra

Subbiano

Philippe

฿4,146 total

includes taxes & fees

14 Dec - 15 Dec

A wooden cabin with a curved roof, a wooden deck, and a gravel path leading to the entrance.

10. LE BOTTI FIORENTINE

Reggello

฿6,044 total

includes taxes & fees

15 Dec - 16 Dec

A clear blue pool with lounge chairs and umbrellas, surrounded by trees and a hill in the background.

11. Relais Santa Margherita

Capolona

Anonymous traveller

A spa area with a stone-walled arch, a hot tub, and a small window.

12. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

฿4,203 total

includes taxes & fees

22 Nov - 23 Nov

13. 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

฿5,988 total

includes taxes & fees

15 Nov - 16 Nov

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Find holiday rentals that suit your style

Top Penna Hotel Reviews

Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

10/10 Excellent

Mona

A buffet with various food items and utensils.

Hotel Il Viandante

Terranuova Bracciolini

10/10 Excellent

James

A courtyard with stone flooring, arched walkways, and a central fountain.

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

10/10 Excellent

Natasha

A stone building with outdoor seating and a pool in the background.

B&B Country House Poggio del Drago

Civitella in Val di Chiana

10/10 Excellent

My husband and I had a wonderful stay at Poggio del Drago - Emanuele is a perfect host and made us feel very welcome throughout our stay. The room itself was lovely - recently renovated and looking lovely. The pool is perfectly located, overlooking the olive groves and with plenty of loungers for all guests. Breakfast was great - a large breakfast table where all guests sat together and took breakfast - an array of sliced meats, cereals, and also a coffee machine to make yourself a cappuccino or...

katy

Villa Cassia di Baccano

Loro Ciuffenna

10/10 Excellent

Antonio

A grassy field with tall trees and a clear sky.

Albergo Villa San Michele

Greve in Chianti

10/10 Excellent

This was an amazing stay and definitely one of our favourite places we stayed in Tuscany. The room was spacious, comfortable, and beautifully presented, and the whole property was absolutely beautiful. Alice and Daniele, who run the place, were amazing hosts. They were so welcoming and helpful, and the service throughout our stay was excellent. We absolutely loved our time here and would happily stay again!

Sharon

A luxurious room with a chandelier, classical columns, and a dining area with wooden chairs and a table.

Dimora Casa Eugenia

Loro Ciuffenna

10/10 Excellent

Simon

A villa with a swimming pool, surrounded by lush greenery and hills in the background.

Viesca Toscana Suites & Villas

Reggello

10/10 Excellent

We had an absolutely incredible stay at Viesca. The setting is beautiful. The photos don't do it justice. The room was spacious and spotlessly clean. Concetta welcomed us and kindly showed us around, talked us through the facilities... The pool is lovely, and it was great to be able to play tennis as well. We did not try any of the spa treatments, but there was a really good selection available. Breakfast was varied and delicious. The only negative thing we have to say about it/Viesca is that...

Anonymous traveller

A stone villa with a swimming pool, outdoor seating, and a well-lit patio area.

Chimera Tuscany Resort

Arezzo

10/10 Excellent

Robert

A large building with a swimming pool, outdoor seating, and a view of surrounding hills.

Palagina la Dimora

Figline e Incisa Valdarno

10/10 Excellent

Auste

Find out more about Penna

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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.

Search Holiday Rentals in Penna

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Penna holiday rentals

1. Relais Villa Belpoggio - Residenza d'Epoca

2. Villa Cassia di Baccano

3. Casa Vacanze Le Fornaci

4. Relais Villa Belvedere

5. L' Eroico

6. Locanda Antico Borgo

7. iConic Wellness Resort

8. The Florence Hills Resort & Wellness

9. Villa La Ginestra

10. LE BOTTI FIORENTINE

11. Relais Santa Margherita

12. DormiVeglia B&B

13. Palazzo Tarlati Residenza d'Epoca

Find holiday rentals that suit your style

Top Penna Hotel Reviews

Relais Villa Belpoggio - Residenza d'Epoca

10/10 Excellent

Find out more about Penna

Frequently Asked Questions

Are there holiday rentals in Penna?

What are some of the best holiday rentals that Penna has to offer?

How many holiday rentals are there in Penna?

What can I see and do in Penna?

What are holiday rentals like in Penna?