Penna Vacation Rentals from $71: 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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Our top choices for Penna vacation 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

Mona

$163 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

2. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

$180 nightly

Sep 16 - Sep 17

Total with taxes and fees

A view of a swimming pool with lounge chairs and umbrellas, surrounded by trees and hills.

3. Borgo di Erboli

Cavriglia

$105 nightly

Sep 10 - Sep 11

Total with taxes and fees

A pool area with a water slide and a stage for performances.

4. Hu Norcenni Girasole Village

Figline e Incisa Valdarno

Hannah

$65 nightly

Sep 6 - Sep 7

Total with taxes and fees

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

5. Casa Vacanze Le Fornaci

Pergine Valdarno

Lisette

$165 nightly

Sep 28 - Sep 29

Total with taxes and fees

A wooden structure with a circular door, surrounded by a garden with string lights and a view of distant mountains.

6. LE BOTTI FIORENTINE

Reggello

$167 nightly

Sep 8 - Sep 9

Total with taxes and fees

A swimming pool with a wooden deck, a tree with red leaves, and a building with a beige facade.

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

Figline Valdarno

$123 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

8. Relais Villa Belvedere

Figline e Incisa Valdarno

Janet

$100 nightly

Oct 2 - Oct 3

Total with taxes and fees

A dining area with a brick archway, wooden dining table, chairs, and a chandelier.

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

Montevarchi

$335 nightly

Sep 16 - Sep 17

Total with taxes and fees

A row of mobile homes with a gravel driveway and trees providing shade.

10. Mobile home with air conditioning and 3 shared pools

Bucine

$168 nightly

Sep 3 - Sep 4

Total with taxes and fees

A stone building with arched windows and a gravel driveway.

11. Villa La Ginestra

Subbiano

Philippe

$108 nightly

Sep 17 - Sep 18

Total with taxes and fees

A swimming pool with a clear blue water surface, surrounded by a well-lit deck area with outdoor seating.

12. Villa Il Palagio

Rignano sull'Arno

Yvonne

$93 nightly

Sep 2 - Sep 3

Total with taxes and fees

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

13. L' Eroico

Gaiole in Chianti

Angela

$164 nightly

Sep 27 - Sep 28

Total with taxes and fees

14. Villa Norcenni Aparthotel

Figline e Incisa Valdarno

Laka

$112 nightly

Sep 2 - Sep 3

Total with taxes and fees

A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

15. Villa di Sotto

Castelnuovo Berardenga

Philippe

$150 nightly

Sep 21 - Sep 22

Total with taxes and fees

A market with a sign reading "BAR IL POGGETTO MARKET".

16. Camping Village Il Poggetto.

Rignano sull'Arno

Alex

$62 nightly

Oct 1 - Oct 2

Total with taxes and fees

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

17. 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

$106 nightly

Oct 2 - Oct 3

Total with taxes and fees

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

18. The Florence Hills Resort & Wellness

Pelago

Linda

$78 nightly

Sep 6 - Sep 7

Total with taxes and fees

19. 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

$126 nightly

Sep 3 - Sep 4

Total with taxes and fees

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

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

Ruffoli

"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...

James

$186 nightly

Sep 4 - Sep 5

Total with taxes and fees

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Top Penna Hotel Reviews

La Certosa di Pontignano

10/10 Excellent

"Beautiful place, very quiet, in love with gardens"

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"This is a very special Tuscan style hotel in the beautiful countryside surrounded by vineyards and olive groves. The staff were excellent, special mention goes to Elisa ,and the food was amazing. My only feedback, if you pay for a treatment the other spa facilities should be included. Also, the gym is very small but let's I wasn't there to train."

Palagina la Dimora

10/10 Excellent

"Beautiful to stay in the main house. The breakfasts were great to start the day - really enjoyed sitting around the pool, nice and peaceful with amazing view. Rooms were comfortable. Easy to get out and try local restaurants and visit other places. Only think for us is it could do with a gym - if you're onsite all day, this would have just made the place perfect."

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."

Find out more about Penna

Everything you need to know about Penna vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Penna vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Penna vacation 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 low season months. For more hustle and bustle, you may prefer to visit Penna in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $71 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Penna rentals

At Expedia, we put the best Penna vacation 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 vacation.

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 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.

Room 1

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. Hu Norcenni Girasole Village

5. Casa Vacanze Le Fornaci

6. LE BOTTI FIORENTINE

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

8. Relais Villa Belvedere

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

10. Mobile home with air conditioning and 3 shared pools

11. Villa La Ginestra

12. Villa Il Palagio

13. L' Eroico

14. Villa Norcenni Aparthotel

15. Villa di Sotto

16. Camping Village Il Poggetto.

17. Locanda Antico Borgo

18. The Florence Hills Resort & Wellness

19. Palazzo Tarlati Residenza d'Epoca

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

Find vacation rentals that suit your style

Top Penna Hotel Reviews

La Certosa di Pontignano

Villa Pitiana

Borgo Scopeto Wine & Country Relais

Castello Vicchiomaggio

Palagina la Dimora

Villa Casagrande Resort & SPA

Hotel Villa Campomaggio

Hotel Fattoria degli Usignoli

Belvedere di San Leonino

Find out more about Penna

Frequently asked questions