Penna Vacation Rentals

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Our top choices for Penna vacation rentals

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is CA $223
CA $246 total
includes taxes & fees
May 18 - May 19
Villa Cassia di Baccano

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 CA $170
CA $187 total
includes taxes & fees
Apr 23 - Apr 24
Villa La Ginestra

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
The price is CA $345
CA $386 total
includes taxes & fees
Apr 27 - Apr 28
Castello di Gargonza

Dolce Casa 2 Summary:

Dolce Casa 2 Summary:
Arezzo
The price is CA $124
CA $173 total
includes taxes & fees
Apr 20 - Apr 21
Dolce Casa 2 Summary:

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (29 reviews)
"Lovely relaxation options and wonderful restaurant attached to the property! Great for a stay where you are travelling through Tuscany by car! Do not recommend travelling by public transport or taxi as it is very expensive."
Australia
Amelia
The price is CA $215
CA $236 total
includes taxes & fees
May 18 - May 19
Villa di Sotto

Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
The price is CA $133
CA $246 total
includes taxes & fees
Apr 20 - Apr 21
Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (313 reviews)
"Beautiful place for family "
Canada
Ismail
Hu Norcenni Girasole Village

Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
9.8 out of 10, Exceptional, (10 reviews)
"Great food in the area. Beautiful church tour and a fantastic host for our stay!"
United States
Craig & Conny M.
The price is CA $211
CA $306 total
includes taxes & fees
Apr 20 - Apr 21
Chianti Craft House Badia a Passignano

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is CA $132
CA $152 total
includes taxes & fees
Apr 27 - Apr 28
DormiVeglia B&B

B&B da Ronald...a Pian del Papa

B&B da Ronald...a Pian del Papa
Pratovecchio Stia
8.0 out of 10, Very good, (11 reviews)
"Venlig betjening Primitivt Ingen varmt vand Meget koldt værelse"
Denmark
Mikael
The price is CA $108
CA $118 total
includes taxes & fees
Apr 21 - Apr 22
B&B da Ronald...a Pian del Papa

Deluxe room Cartazucchero in the heart of Arezzo

Deluxe room Cartazucchero in the heart of Arezzo
Arezzo Centro Storico
10.0 out of 10, Exceptional, (2 reviews)
"From all the places we stayed during our 13-day trip to Italy, this was by far our favorite. Fabio was incredibly communicative and friendly right from the start, sending us clear instructions on how to get there. He greeted us at the door with such warmth that it truly felt like we were staying with family. The room was spotless, beautifully decorated, and generously stocked with water, cookies, pastries, and other treats. It had the comfort and attention to detail of a hotel, yet the warmth of...
United States
Hector
The price is CA $116
CA $128 total
includes taxes & fees
Apr 27 - Apr 28
Deluxe room Cartazucchero in the heart of Arezzo

Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is CA $179
CA $203 total
includes taxes & fees
Apr 19 - Apr 20
Residenzia del Sogno

iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (36 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is CA $122
CA $144 total
includes taxes & fees
May 4 - May 5
iConic Wellness Resort

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (22 reviews)
"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "
United States
Massimo
The price is CA $351
CA $399 total
includes taxes & fees
Apr 23 - Apr 24
Borgo Argenina

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (13 reviews)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
The price is CA $222
CA $257 total
includes taxes & fees
May 17 - May 18
L' Eroico

Camping Village Il Poggetto.

Camping Village Il Poggetto.
3.0 star property
Rignano sull'Arno
8.0 out of 10, Very good, (66 reviews)
"Pet friendly and clean"
United Kingdom
Nancy
The price is CA $92
CA $107 total
includes taxes & fees
Apr 18 - Apr 19
Camping Village Il Poggetto.

House Il Cipresso in the heart of Chianti with swimming pool

House Il Cipresso in the heart of Chianti with swimming pool
Castellina in Chianti
10.0 out of 10, Exceptional, (1 review)
"Beautiful setting with a rustic and friendly vibe. The place was clean and well-kept. We enjoyed every minute! A bonus was that the nights were cool (did t need the AC), and we slept with the windows open, despite the heat during the day."
Canada
Jon M.
House Il Cipresso in the heart of Chianti with swimming pool

Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is CA $121
CA $140 total
includes taxes & fees
Apr 21 - Apr 22
Mariani Bed & Breakfast

Borgo Argiano

Borgo Argiano
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (76 reviews)
"Very comfortable stay. "
United States
Victor
The price is CA $386
CA $437 total
includes taxes & fees
May 12 - May 13
Borgo Argiano

Holiday Home 'Gigli Di Firenze' with Mountain View, Wi-Fi and Air Conditioning

Holiday Home 'Gigli Di Firenze' with Mountain View, Wi-Fi and Air Conditioning
Rufina
10.0 out of 10, Exceptional, (3 reviews)
"Très bel accueil et explications en arrivant, toute la famille nous a accueilli et a tout fait pour nous rendre service, la maison est grande et bien complète, la terrasse bien exposée et l’emplacement pour garer la voiture est un plus, je recommande fortement ! "
United States
Olivier M.
The price is CA $185
CA $288 total
includes taxes & fees
Apr 18 - Apr 19
Holiday Home 'Gigli Di Firenze' with Mountain View, Wi-Fi and Air Conditioning
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

Find out more about Penna

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Penna. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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. San Pietro a Gropina and Croce del Pratomagno 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.