Penna Vacation Rentals

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Check prices for these dates

Tonight
Dec 9 - Dec 10
Tomorrow
Dec 10 - Dec 11
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Our top choices for Penna vacation rentals

Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Relais Villa Belvedere

Relais Villa Belvedere

Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (70)
"Very nice place"
United States
Maria
The price is NT$3,165
NT$3,535 total
includes taxes & fees
Dec 15 - Dec 16
Relais Villa Belvedere
View from room
The Florence Hills Resort & Wellness

The Florence Hills Resort & Wellness

Pelago
8.8 out of 10, Excellent, (175)
"Great stay would recommend "
United Kingdom
Luan
The Florence Hills Resort & Wellness
Terrace/patio
Borgo Argiano

Borgo Argiano

Castelnuovo Berardenga
10.0 out of 10, Exceptional, (73)
"Borgo Argiano is a beautiful property, very well run by Dario and staff. We highly recommend staying there if you are interested in exploring the Tuscan region. The apartments are large and they stock the kitchen for convenience It is also a winery and you could get a tour was well as a tasting of the delicious wines."
United States
Aurora
Borgo Argiano
Front of property - evening/night
Villa Il Palagio

Villa Il Palagio

Rignano sull'Arno
8.6 out of 10, Excellent, (60)
"The best place in the region"
United Kingdom
Kamen
Villa Il Palagio
View from property
Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca

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 NT$5,115
NT$5,627 total
includes taxes & fees
Dec 11 - Dec 12
Relais Villa Belpoggio - Residenza d'Epoca
Panoramic Apartment, 2 Bedrooms, Balcony, Hill View | Terrace/patio
Borgo Argenina

Borgo Argenina

Gaiole in Chianti
9.8 out of 10, Exceptional, (22)
"A planned Tuscany trip in the making for over a year. Saw this property came up while doing research and had a wonderful and romantic history. The property was even more beautiful than the pictures posted. It definitely caters to all types of travellers. A perfect bed and breakfast stay. Definitely recommend and will be back again. "
Canada
Nancy
Borgo Argenina
Seasonal outdoor pool
Agriturismo La Ferrozzola

Agriturismo La Ferrozzola

Castellina in Chianti
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
Panoramic Apartment, Hill View (4) | Terrace/patio
Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi

Castellina in Chianti
8.0 out of 10, Very Good, (2)
"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 NT$3,742
NT$4,334 total
includes taxes & fees
Jan 7 - 2026/1/8
Casa Vacanze Squarcialupi
Terrace/patio
Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci

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 NT$4,092
NT$4,610 total
includes taxes & fees
Jan 3 - 2026/1/4
Casa Vacanze Le Fornaci
Exterior
Podere La Chiusella

Podere La Chiusella

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
Seasonal outdoor pool
Mobile Home max 6 pax

Mobile Home max 6 pax

3.0 star property
Rignano sull'Arno
8.0 out of 10, Very Good, (65)
"Second stay at this property but got a 3 bed 2 bath cabin this time. Happy with most things could have had more housekeeping for a ten day stay. Great base to explore Tuscany excellent bar especially the staff as well as a nice restaurant "
Australia
Rebecca
Mobile Home max 6 pax
Seasonal outdoor pool, pool umbrellas, sun loungers
Borgo dei Corsi Holiday House

Borgo dei Corsi Holiday House

Ortignano Raggiolo
9.0 out of 10, Wonderful, (16)
"Very relaxing place, we really enjoyed it specially walking in the mountains! "
United States
Candida
Borgo dei Corsi Holiday House
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

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort

10/10 Excellent
"Very clean,staff was very kind and helpful. Looking forward to come back! 😊"
Andrea 2-night trip
Posted 20 hours ago
Castello di Fonterutoli Wine Resort

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:

  • View our selection of featured holiday rentals in Penna
  • Use the map to find apartments and other holiday homes in the Penna neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Penna while they last

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 home 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 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. 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.