Penna holiday homes

We found 834 holiday rentals — enter your dates for availability

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August 2025

September 2025

Discover a selection of 6 homes and other holiday rentals in Penna that are perfect for your trip. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as air conditioning and a pool. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Penna

Showing deals for:31 Oct - 7 Nov

Exceptional

(9 reviews)

Purgatorio house, a typical Tuscan structure with pool, surrounded by nature.

Ortignano Raggiolo, Tuscany

8% off

NZ$271 per night

includes taxes & fees

Exceptional

(10 reviews)

Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany

Bucine, Tuscany

24% off

NZ$4,029 per night

includes taxes & fees

Exceptional

(9 reviews)

Lake House, Farm in the hills between Arezzo Florence Siena, Garden, Pool

Pergine Valdarno, Tuscany

12% off

NZ$207 per night

includes taxes & fees

The Casa Colonica is located in the hamlet of il Poggiolo.

Exceptional

(29 reviews)

Tuscan Villa with Panoramic View - near Florence, Siena & Arezzo

Bucine, Tuscany

8% off

NZ$413 per night

includes taxes & fees

Exceptional

(10 reviews)

La Vecchia Posta | Charming home near Chianti and Art Cities – 2 Beds, 3 Baths

Cavriglia, Toscana

18% off

NZ$347 per night

includes taxes & fees

Exceptional

(28 reviews)

HillsideVilla overlooking the Tuscan landscape between Florence Arezzo and Siena

Loro Ciuffenna, Tuscany

6% off

NZ$429 per night

includes taxes & fees

Wonderful

(7 reviews)

House / Villa - Ortignano-RaggioloHouse with garden (Florance and Arezzo)

Ortignano Raggiolo, Tuscany

5% off

NZ$429 per night

includes taxes & fees

Exceptional

(10 reviews)

Apt. LaTraviata - Residence Casa lama - two-room apartment 2/4 P for couples or families

Castelfranco di Sopra, Tuscany

10% off

NZ$167 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Penna

Showing deals for: 31 Oct - 3 Nov

Ancient farm situated in the heart of the Chianti Classico Senese, Pool and View

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 home

NZ$320 per night

includes taxes & fees

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

Sleeps 2 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

NZ$293 per night

includes taxes & fees

Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.

Sleeps 4 · 2 bedrooms · 1+ bathroom

for 3 nights, 1 home

NZ$354 per night

includes taxes & fees

CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

Sleeps 4 · 2 bedrooms · 1 bathroom

for 3 nights, 1 room

NZ$435 per night

includes taxes & fees

Villa with large garden in the Chianti hills

Sleeps 5 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

NZ$234 per night

includes taxes & fees

Family apartment with magical view on the old city, balcony, wifi & parking

Sleeps 4 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 apartment

NZ$390 per night

includes taxes & fees

Top rated rentals - Penna

Premier Host

Fantastic family holiday

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Explore the natural setting in Penna

Learn about the unique charm of Penna with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Penna

Do you want to find attractions to see while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Penna a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

Le Miccine (7.4 mi / 12 km)
Badia a Coltibuono (9.4 mi / 15.2 km)
Castello di Albola (10.9 mi / 17.5 km)
Cantalici Winery (11.5 mi / 18.5 km)
Villa a Sesta Polo Club (12.6 mi / 20.3 km)
Castello di Radda Winery (13 mi / 20.9 km)

Exploring the natural landscape of Penna

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Penna is a great place to get out in nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

Piazza Guido Monaco (15.2 mi / 24.5 km)
Arno River (22.3 mi / 35.9 km)
Riserva Naturale Regionale Valle dell'Inferno e Bandella (4.5 mi / 7.3 km)
Valle dell'Inferno e Bandella (4 mi / 6.4 km)
Gianfranco Carla Fineschi Botanical Rose Garden (5.9 mi / 9.4 km)
Area Naturale Protetta di Interesse Locale Arboreto Monumentale di Moncioni (7.9 mi / 12.8 km)

Travelling to and around Penna

The nearest airport is in Peretola Airport (FLR), located 26.1 mi (42 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Penna?

Houses are the most popular style of holiday home in Penna, according to our data. Even if you have a different idea about what you want, Bookabach has properties in loads of shapes and sizes. Explore our options to find your ideal match.

How much does it cost to rent a holiday home in Penna?

A range of things influence how much you pay for a holiday home in Penna, such as the type of property, length of stay and season. However, all Bookabach homes have one thing in common — unbeatable value. Just enter your travel dates to find your ideal escape.

How much does it cost to rent a beach house in Penna?

The average price for a holiday home near the beach in Penna will depend on when you'll be there and the type and size of property you want. You can easily find prices on Bookabach by entering the dates you'll be travelling. Then use the handy filters to pick the number of bedrooms and amenities important to you, such as WiFi, a pool and air conditioning.

What are popular home amenities in Penna?

The most popular home amenities people are searching for in Penna are a swimming pool, a garden and an oven. Whether you're travelling with pals, family or even pets, Bookabach holiday homes include the best amenities for fun and relaxation with the people you cherish the most.

What are the top attractions for families in Penna?

If you're looking for some fun for the whole family near the heart of Penna, head over to Valle dellInferno e Bandella.

How old do you have to be to rent a holiday home in Penna?

The minimum age is typically 16, 18 or 21. It can vary from one property to another on Bookabach, so look at the rules of your chosen Penna stay before making a booking.

How long can I rent a holiday home in Penna for?

How long you can rent a holiday home in Penna differs according to the property. Simply enter your chosen dates to look at a list of options offering extended stays. With lots of amenities such as kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to discover somewhere perfect to call your home away from home in Penna.