Penna Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Penna vacation rentals

Lobby

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 ￥22,139
￥24,352 total
includes taxes & fees
Apr 10 - Apr 11
Villa Cassia di Baccano
Front of property

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 ￥21,134
￥23,247 total
includes taxes & fees
Apr 9 - Apr 10
Villa La Ginestra
Lunch and dinner served, local cuisine

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 ￥37,046
￥41,488 total
includes taxes & fees
Mar 30 - Mar 31
Castello di Gargonza
Exterior

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 ￥28,044
￥32,325 total
includes taxes & fees
Mar 31 - Apr 1
Borgo Argenina
Interior

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 ￥24,077
￥35,147 total
includes taxes & fees
Mar 30 - Mar 31
Chianti Craft House Badia a Passignano
Exterior

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 ￥25,839
￥29,898 total
includes taxes & fees
Mar 31 - Apr 1
L' Eroico
Exterior

La Vigna by Interhome

La Vigna by Interhome
Greve in Chianti
The price is ￥46,124
￥46,862 total
includes taxes & fees
Mar 31 - Apr 1
La Vigna by Interhome
Lounge

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 ￥16,564
￥18,958 total
includes taxes & fees
Apr 17 - Apr 18
Mariani Bed & Breakfast
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (28 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 ￥23,243
￥25,567 total
includes taxes & fees
Apr 29 - Apr 30
Villa di Sotto
Property grounds

Dolce Casa 2 Summary:

Dolce Casa 2 Summary:
Arezzo
The price is ￥14,144
￥19,688 total
includes taxes & fees
Mar 31 - Apr 1
Dolce Casa 2 Summary:
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers

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 ￥12,227
￥14,556 total
includes taxes & fees
Apr 19 - Apr 20
iConic Wellness Resort
Interior

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
The price is ￥85,050
￥101,539 total
includes taxes & fees
Mar 30 - Mar 31
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Front of property

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (64 reviews)
"Great stay but can feel a bit captive to their restaurant for dinner. Min 2 courses mandatory per person and dessert doesn’t count "
Canada
Shelley
The price is ￥26,888
￥31,053 total
includes taxes & fees
Apr 22 - Apr 23
Villa Curina Resort
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (27 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is ￥16,108
￥18,457 total
includes taxes & fees
Mar 31 - Apr 1
DormiVeglia B&B
Family Apartment, 2 Bedrooms, Hill View, Tower | View from room

Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
9.4 out of 10, Exceptional, (3 reviews)
"We absolutely loved our stay at this hotel. The suite was perfect and the restaurant had probably the best food I have had in Tuscany. We definitely plan to stay there again."
United States
Gregory
The price is ￥20,295
￥22,877 total
includes taxes & fees
Mar 30 - Mar 31
Casa Vacanze Le Fornaci
Outdoor dining

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 ￥14,546
￥16,000 total
includes taxes & fees
Mar 30 - Mar 31
Deluxe room Cartazucchero in the heart of Arezzo
Exterior

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 ￥15,221
￥28,136 total
includes taxes & fees
Apr 8 - Apr 9
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Exterior

Taverna by Interhome

Taverna by Interhome
Greve in Chianti
The price is ￥69,002
￥69,740 total
includes taxes & fees
Mar 30 - Mar 31
Taverna by Interhome
Panoramic Apartment (2) | Terrace/patio

Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
8.8 out of 10, Excellent, (3 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is ￥20,625
￥23,795 total
includes taxes & fees
Mar 30 - Mar 31
Casa Vacanze Squarcialupi
Free daily buffet breakfast

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (72 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is ￥70,986
￥78,823 total
includes taxes & fees
Apr 2 - Apr 3
Terre di Baccio
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

Borgo Del Cabreo

Borgo Del Cabreo

10/10 Excellent
"Staff was fantastic, grounds were well groomed, rooms looked recently refurbished and breakfast was wonderful. "
eric 3-night trip
Posted 5 days ago
Borgo Del Cabreo

Find out more about Penna

Search for holiday rentals in Penna on Expedia! You can easily find your home rentals, villas, holiday apartments in Penna using one of the methods below:

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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 a coffee 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.