Penna Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Penna

Premium bedding, down duvets, in-room safe, blackout curtains
Terre di Baccio

Townhouse in Greve in Chianti

9.8 out of 10, Exceptional, (71)
"Great hotel in a beautiful location with fantastic staff. "
United Kingdom
Mark
Terre di Baccio
Lobby lounge
Villa Cassia di Baccano

Townhouse in Loro Ciuffenna

9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is S$194
includes taxes & fees
30 Nov - 1 Dec
Villa Cassia di Baccano
Daily buffet breakfast (EUR 10 per person)
DormiVeglia B&B

Townhouse in Monte San Savino

10.0 out of 10, Exceptional, (27)
"This was our favourite B&B. The owner Simona was absolutely wonderful. The hot tub in our room was out of this world. If you have the chance to visite this gem…DO IT!!"
Canada
Claude
DormiVeglia B&B
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Relais Villa Belvedere

Aparthotel in Figline e Incisa Valdarno

9.2 out of 10, Wonderful, (69)
"Very nice place"
United States
Maria
The price is S$133
includes taxes & fees
8 Dec - 9 Dec
Relais Villa Belvedere
Premium bedding, down duvets, pillow-top beds, minibar
THE MONNA LISA RESORT

Townhouse in Arezzo

9.6 out of 10, Exceptional, (8)
"Massimiliano was a great host, but we were the only guests and the restaurant was closed. The hotel was basically unmanaged. It should not have been listed as a hotel. "
United States
Bart
The price is S$183
includes taxes & fees
5 Dec - 6 Dec
THE MONNA LISA RESORT
Exterior
Podere La Chiusella

Aparthotel in Rapolano Terme

9.4 out of 10, Exceptional, (30)
"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
Front of property
L' Eroico

Townhouse in Gaiole in Chianti

10.0 out of 10, Exceptional, (12)
"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
Breakfast, lunch, dinner served; Regional cuisine
La Locanda di Pietracupa

Townhouse in Barberino Tavarnelle

9.4 out of 10, Exceptional, (35)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa
Front of property
Locanda Antico Borgo

Townhouse in Civitella in Val di Chiana

9.2 out of 10, Wonderful, (20)
"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. "
United Kingdom
Mr Andy
The price is S$164
includes taxes & fees
30 Nov - 1 Dec
Locanda Antico Borgo
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
Villa La Ginestra

Townhouse in Subbiano

9.6 out of 10, Exceptional, (5)
"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."
Canada
Philippe
Villa La Ginestra
Garden
La Murata

Aparthotel in Rapolano Terme

9.0 out of 10, Wonderful, (11)
"Amazingly beautiful place! Wish i could have stayed longer to enjoy the view but was just passing through. The apartment was so cute and clean. Any family would enjoy staying here. I would stay here again if i were in the area."
United States
Elizabeth
The price is S$207
includes taxes & fees
29 Nov - 30 Nov
La Murata
View from property
Relais Villa Belpoggio - Residenza d'Epoca

Residence in Loro Ciuffenna

9.8 out of 10, Exceptional, (35)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is S$233
includes taxes & fees
28 Nov - 29 Nov
Relais Villa Belpoggio - Residenza d'Epoca
Terrace/patio
Casa Vacanze Le Fornaci

Apartment in Pergine Valdarno

9.4 out of 10, Exceptional, (3)
"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 S$197
includes taxes & fees
30 Nov - 1 Dec
Casa Vacanze Le Fornaci
Seasonal outdoor pool
Agriturismo La Ferrozzola

Holiday Home in Castellina in Chianti

9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
Balcony
Cameracaffè Centro

Townhouse in Arezzo Centro Storico

8.6 out of 10, Excellent, (178)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
The price is S$120
includes taxes & fees
3 Dec - 4 Dec
Cameracaffè Centro
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.
View all properties

Black Friday Sale

Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Penna Hotel Reviews

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort

10/10 Excellent
"Amazing experience! The staff were very knowledgeable and helpful in setting up our dinner and wine tour. Room had a beautiful view. This was the best part of our journey through Italy. Keep up the great work! A+ "
Andre 1-night trip
Posted 8 days ago
Castello di Fonterutoli Wine Resort

Frequently asked questions

Are there holiday rentals in Penna?

Yes, there are holiday rentals close to the most popular sights in Penna, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Penna has to offer?

Borgo Argiano: This holiday home rental outside of Penna is located on a river, and has a balcony, a terrace and a BBQ 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 holiday with a garden and a library.

How many holiday rentals are there in Penna?

Choose from 3 Expedia holiday rentals in Penna for a memorable holiday.

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 wider area.

What are holiday rentals like in Penna?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Penna. Holiday rentals feature extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.