Penna Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

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 P7,623
P8,386 total
includes taxes & fees
Jun 17 - Jun 18
Villa Cassia di Baccano
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (65 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 P8,585
P10,017 total
includes taxes & fees
Jun 21 - Jun 22
Villa Curina Resort
Lunch and dinner served

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
The price is P15,475
P17,309 total
includes taxes & fees
Jun 10 - Jun 11
Castello di Gargonza
View from room

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
The price is P5,500
P6,336 total
includes taxes & fees
Jun 9 - Jun 10
The Florence Hills Resort & Wellness
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

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
The price is P9,922
P10,914 total
includes taxes & fees
Jun 18 - Jun 19
Villa di Sotto
Exterior

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (319 reviews)
"Beautiful place for family "
Canada
Ismail
The price is P3,703
P4,288 total
includes taxes & fees
Jun 11 - Jun 12
Hu Norcenni Girasole Village
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 P9,342
P10,850 total
includes taxes & fees
Jul 1 - Jul 2
L' Eroico
Private spa tub

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 P6,706
P7,663 total
includes taxes & fees
Jun 7 - Jun 8
DormiVeglia B&B
Outdoor pool

Villa Rosa Panzano

Villa Rosa Panzano
Greve in Chianti
8.2 out of 10, Very Good, (53 reviews)
"The facilities were great, including access to the swimming pool. The staff were very friendly and helpful. Breakfast options were good. Parking on site. Villa is a 10 minute drive to two lovely Tuscan towns (Greve and Panzano). Would stay here again - it was so atmospheric! "
United Kingdom
Rachel
The price is P7,819
P8,887 total
includes taxes & fees
Jun 8 - Jun 9
Villa Rosa Panzano
Exterior

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
The price is P11,389
P13,102 total
includes taxes & fees
Jun 7 - Jun 8
Borgo Argenina
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 P7,037
P7,741 total
includes taxes & fees
Jun 16 - Jun 17
Villa La Ginestra
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

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 P8,372
P9,495 total
includes taxes & fees
Jun 16 - Jun 17
Residenzia del Sogno
Front of property

Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.4 out of 10, Exceptional, (31 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
The price is P8,029
P9,119 total
includes taxes & fees
Jun 30 - Jul 1
Podere La Chiusella
Porch

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (185 reviews)
"This property met all our needs for a one night stay. It is conveniently located near the train station and near the old town area. The people we encountered were friendly and helpful. The breakfast choices were plentiful and the breakfast area on the rooftop patio was beautiful. The only negative was that the walks of the room were thin and we could hear neighbors quite a bit. "
United States
Roger
The price is P6,060
P7,096 total
includes taxes & fees
Jun 17 - Jun 18
Cameracaffè Centro
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, (37 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is P6,040
P7,074 total
includes taxes & fees
Jun 7 - Jun 8
iConic Wellness Resort
Exterior

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
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 P6,489
P7,424 total
includes taxes & fees
Jun 9 - Jun 10
Mariani Bed & Breakfast
View from room

Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
9.6 out of 10, Exceptional, (5 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 P8,972
P10,084 total
includes taxes & fees
Jun 7 - Jun 8
Casa Vacanze Le Fornaci
Exterior

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 P5,190
P5,709 total
includes taxes & fees
Jul 3 - Jul 4
B&B da Ronald...a Pian del Papa
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 Vescine

Borgo Vescine

10/10 Excellent
"We enjoyed our stay immensely. The staff was very accommodating, especially with our two year old. The activities we did (movie night- included; dinner in the olive grove, truffle hunting, & a cooking class- paid) were all lovely experiences. We loved the property grounds."
Christina 4-night trip
Posted 11 hours ago
Borgo Vescine

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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Look no further and take a look at our great range of rental properties in Penna!

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: You might want to consider this vacation rental near Penna, which 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. 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.