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
$267 nightly
The price is $294
May 28 - May 29
Total with taxes and fees
Villa Cassia di Baccano

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
DormiVeglia B&B

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
Villa La Ginestra

Dolce Casa 2 Summary:

Dolce Casa 2 Summary:
Arezzo
$125 nightly
The price is $125
May 20 - May 21
Total with taxes and fees
Dolce Casa 2 Summary:

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (32 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
Villa di Sotto

The Florence Hills Resort & Wellness

The Florence Hills Resort & Wellness
Pelago
8.8 out of 10, Excellent, (177 reviews)
"Enjoyed our stay and breakfast was great. "
Canada
Linda
$111 nightly
The price is $129
Jun 1 - Jun 2
Total with taxes and fees
The Florence Hills Resort & Wellness

Camping Village Il Poggetto.

Camping Village Il Poggetto.
3.0 star property
Rignano sull'Arno
8.0 out of 10, Very Good, (69 reviews)
"Pet friendly and clean"
United Kingdom
Nancy
$62 nightly
The price is $71
May 20 - May 21
Total with taxes and fees
Camping Village Il Poggetto.

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (316 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
10.0 out of 10, Exceptional, (11 reviews)
"Great food in the area. Beautiful church tour and a fantastic host for our stay!"
United States
Craig & Conny M.
$207 nightly
The price is $212
May 19 - May 20
Total with taxes and fees
Chianti Craft House Badia a Passignano

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

Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.4 out of 10, Exceptional, (30 reviews)
"Et sjarmerende lite B&B. Har nok vært utrolig vakkert i sine glansdager, men områdene rundt bærer preg av lite vedlikehold. Leiligheten var helt grei for en overnatting. Gulvet på badet var ikke rent. Når vi tørket opp etter oss ble håndkleet møkkete. Men overnattingen var helt grei alt i alt. Når vi skulle sjekke ut var det ikke et menneske å se, resepsjonen var stengt. Endte med å sette nøklene i døra og dra da alt var betalt ved bestilling."
Norway
Elisabeth
Podere La Chiusella

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
$179 nightly
The price is $179
May 28 - May 29
Total with taxes and fees
Tolletta 10 e Lode - One Bedroom House, Sleeps 4

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
Mariani Bed & Breakfast

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
L' Eroico

Residence Poggio del Golf

Residence Poggio del Golf
Impruneta
9.2 out of 10, Wonderful, (11 reviews)
"À 20 minutes de Florence très bien et agréable Personel très Shympa tique "
France
Jean philippe
Residence Poggio del Golf

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
$97 nightly
The price is $114
May 20 - May 21
Total with taxes and fees
iConic Wellness Resort

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (23 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
Borgo Argenina

Villa Norcenni Aparthotel

Villa Norcenni Aparthotel
2.0 star property
Figline e Incisa Valdarno
7.4 out of 10, Good, (21 reviews)
"It was clean and safe."
United Kingdom
Laka
Villa Norcenni Aparthotel

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
$108 nightly
The price is $118
May 20 - May 21
Total with taxes and fees
Deluxe room Cartazucchero in the heart of Arezzo

Villa Cristina

Villa Cristina
Castellina in Chianti
7.8 out of 10, Good, (39 reviews)
"Arnaque absolue par rapport aux photos. Sdb salle moisi partout, wc jaune de calcaire. Aucune isolation phonique. Photos ne correspondent pas Chambre dans garage hauteur sous planfond nulle obligé de se baisser."
France
pascal
Villa Cristina
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

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 $59 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 electric kettle. 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. Mulino Ad Acqua 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.