Penna Holiday Rentals from NZ$138: Search Short-Term Rentals

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

1. Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

Kristina

includes taxes & fees

15 Nov - 16 Nov

A cozy living room with a stone wall, a wine rack, and two sofas.

2. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

includes taxes & fees

8 Nov - 9 Nov

A wooden table with two chairs on a balcony, overlooking a lush green landscape with trees and hills.

3. Casa Vacanze Le Fornaci

Pergine Valdarno

Lisette

includes taxes & fees

10 Nov - 11 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

includes taxes & fees

9 Nov - 10 Nov

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

5. L' Eroico

Gaiole in Chianti

Angela

includes taxes & fees

12 Nov - 13 Nov

A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

6. Castello di Gargonza

Monte San Savino

Iain

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

7. Terre di Baccio

Greve in Chianti

Gage

includes taxes & fees

8 Nov - 9 Nov

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

8. 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

includes taxes & fees

10 Nov - 11 Nov

A hot tub surrounded by a wooden deck, a covered outdoor seating area, and a circular wooden structure.

9. LE BOTTI FIORENTINE

Reggello

includes taxes & fees

9 Nov - 10 Nov

10. iConic Wellness Resort

Arezzo

Wade

includes taxes & fees

8 Nov - 9 Nov

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

11. The Florence Hills Resort & Wellness

Pelago

Linda

includes taxes & fees

30 Nov - 1 Dec

A hotel room with a bed, a desk with a chair, a wardrobe, a television, and a window with curtains.

12. Limehome Arezzo Duomo

Arezzo Centro Storico

Florian

includes taxes & fees

10 Nov - 11 Nov

A stone building with arched windows and a gravel driveway.

13. Villa La Ginestra

Subbiano

Philippe

includes taxes & fees

9 Nov - 10 Nov

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

includes taxes & fees

8 Nov - 9 Nov

A balcony with potted plants and a view of a cityscape.

15. Cameracaffè Centro

Arezzo Centro Storico

Steven

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a large bed, a fireplace, and a brick ceiling.

16. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

includes taxes & fees

9 Nov - 10 Nov

A modern hotel room with large windows, a bed, a desk, and a chair.

17. B&B 52cento

Arezzo Centro Storico

Tina

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a large bed, a chandelier, a mirror, and plants.

18. Bibi Boutique

Arezzo Centro Storico

Carol

includes taxes & fees

10 Nov - 11 Nov

An outdoor dining table set with plates, cutlery, and wine glasses, surrounded by greenery and flowers.

19. Residence Centanni

Bagno a Ripoli

Merri

includes taxes & fees

8 Nov - 9 Nov

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

20. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

includes taxes & fees

30 Nov - 1 Dec

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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

Anonymous traveller

A spacious lobby with a reception desk, seating area, and a large vase.

Hotel Valdarno

Montevarchi

10/10 Excellent

We arrived at Hotel Valdarno after travelling over 35 hours from Melbourne Australia and stayed to explore Montevarchi the next day. The hotel exceeded my expectations in terms of comfort and 'charm'. The breakfast including organic and gluten-free options was memorable and the staff very helpful. We were travelling on to a village in Chianti so only stayed one night, but will seriously consider basing ourselves in Montevarchi and at hotel Valdarno for future visits to the region. The hotel's...

janet

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

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

10/10 Excellent

Anonymous traveller

A swimming pool with lounge chairs, a stone wall, and a building with a tiled roof.

Viesca Toscana Suites & Villas

Reggello

10/10 Excellent

Katherine

A historic building with multiple stories, surrounded by lush greenery and a well-maintained garden with a central fountain.

Il Borro - Relais & Châteaux

Loro Ciuffenna

10/10 Excellent

This an amazing property in a most beautiful Tuscan setting. The heated infinity pool is incredible. The restaurants are outstanding and the estates wines our brilliant and make sure you book a wine tasting with Florence. The staff and all very friendly and most professional. The view are incredible and our suite was more like a luxurious Tuscan villa, massive bedroom, bathroom and living room including a large dinning table. The property as great walking trails, golf course and even its own...

Peter

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

Leonard

A resort with a large swimming pool, sun loungers, and umbrellas.

Palagina la cascina

Figline e Incisa Valdarno

10/10 Excellent

A cosy place to stay in Tuscany about 30 minutes out of Florence. Super friendly staff and free parking, plus supermarkets close by. Great for self-drive holiday. Unpleasant smell in bathroom possibly from blocked pipes and we couldn't get the air-conditioner working so was challenging to get to sleep as it was warm inside and couldn't leave the window open due to mosquitos. Part of a winery with lovely Tuscan views and farm animals on the property. Overall we enjoyed our stay.

Tim

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$138 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 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.

Penna Holiday Rentals

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. Castello di Gargonza

7. Terre di Baccio

8. Locanda Antico Borgo

9. LE BOTTI FIORENTINE

10. iConic Wellness Resort

11. The Florence Hills Resort & Wellness

12. Limehome Arezzo Duomo

13. Villa La Ginestra

14. Palazzo Tarlati Residenza d'Epoca

15. Cameracaffè Centro

16. DormiVeglia B&B

17. B&B 52cento

18. Bibi Boutique

19. Residence Centanni

20. Agriturismo La Ferrozzola

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

Penna holiday rentals: An excellent choice for every season

How to find incredible deals on Penna rentals

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?