Holiday Rentals in Penna

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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Penna

Relais Villa Belvedere

Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (69)
"Very nice place"
United States
Maria
The price is €94
includes taxes & fees
30 Nov - 1 Dec
Relais Villa Belvedere

17th century farmhouse with private pool and Wi-Fi and air conditioning

Arezzo
9.2 out of 10, Wonderful, (39)
"We stayed as a family of 10 and had a great time. The accommodation is definitely rustic and traditional. It won’t suit everyone but if you’re looking to get back to basics look no further! For us as an Australian family it could have cleaner and we ended up doing cleaning ourselves to make it more comfortable. The bed linen and towels are also ready for a refresh. The host was great and provided a good summary of the local area and sights. Arezzo is a lovely day out. "
Australia
Anonymous traveller
17th century farmhouse with private pool and Wi-Fi and air conditioning

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

Typical Tuscan Country House

Pelago
10.0 out of 10, Exceptional, (128)
"Beautiful home and gracious host!"
United States
Levi M.
Typical Tuscan Country House

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

Ruffoli
9.8 out of 10, Exceptional, (59)
"Great location in the heart Chianti. The host was very welcoming and the apartment was perfect. very comfortable bed and very quiet location. Nice terrace and pool but unfortunately the weather wasnt warm enough for us to enjoy the pool. There is a dirt road to get to the apartment but very easy to navigate so dont be worried about it. Thank you Babette, we hope to have the pleasure of going back sometime."
United States
Andre P.
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

Tuscan villa with infinity salt private pool and jacuzzi on breathtaking view

Pelago
9.8 out of 10, Exceptional, (106)
"Very nice villa with a stunning view. Everything looks much better than on the pictures. I can recommend Anna's villa everyone who is looking for some relaxing days in Tuscany."
Germany
Sven H.
Tuscan villa with infinity salt private pool and jacuzzi on breathtaking view

Stunning villa for 6 people with WIFI, private pool, A/C, TV, patio and pets allowed

Cavriglia
10.0 out of 10, Exceptional, (13)
"Really great stay here.The villa is absolutely beautiful on the outside and inside.Parking was easy (right in front of property).Location was beautiful and hosts were great."
United States
Mohammed S.
Stunning villa for 6 people with WIFI, private pool, A/C, TV, patio and pets allowed

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

Holiday Villa With Swimming Pool In Arezzo.

Castel Focognano
10.0 out of 10, Exceptional, (37)
"We had a superb stay which exceeded our expectations. Andrea the host was very kind and welcoming, the house very complete with all requirements and the views fantastic. "
Netherlands
Henk Jan G.
Holiday Villa With Swimming Pool In Arezzo.

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Castellina in Chianti
10.0 out of 10, Exceptional, (64)
"Gorgeous property - we had a wonderful stay "
United Kingdom
Michelle D.
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

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 €155
includes taxes & fees
28 Nov - 29 Nov
Relais Villa Belpoggio - Residenza d'Epoca

Camping Village Il Poggetto

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
Camping Village Il Poggetto

Private villa in the heart of chianti with view of siena

Fonterutoli
10.0 out of 10, Exceptional, (3)
"Beautiful villa and stunning location. The host was very responsive and helpful. I would love to return someday. "
United States
Wendy F.
Private villa in the heart of chianti with view of siena

Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl

Greve in Chianti (Firenze)
10.0 out of 10, Exceptional, (42)
"Elena and her staff were excellent. They provided us with a welcome dinner which was great after our long trip in, as well as breakfast the next morning. Property is beautiful up in top of a hill overlooking the beautiful landscape. We had 9 people with more than enough room for all of us. Highly recommended!"
United States
Ryan F.
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl

Exclusive villa with gated pool, 12 pax, all-inclusive. 72 reviews, watch video

Toscana
9.8 out of 10, Exceptional, (74)
"Beautiful villa & location. Represented accurately."
United States
Betty Ann T.
Exclusive villa with gated pool, 12 pax, all-inclusive. 72 reviews, watch video

A Panoramic Tuscan Luxury - Villa Maria in Fronzano

Reggello
10.0 out of 10, Exceptional, (75)
"Walk 5 minutes to a village with grocery store or simply sit by the pool to enjoy the view. This villa has it all! Our family of 10 (adults and kids) spent 2 weeks at Villa Maria and would recommend it for its amenities and location. The host, Tomasso, and chef, Donato, were the ultimate guides and helpers. Take the train into Florence to avoid parking a car. Experience Borroncino Restaurant in Reggello for a gastronomic treat. We would certainly return to this heavenly spot for touring...
United States
Maralin G.
A Panoramic Tuscan Luxury - Villa Maria in Fronzano

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

Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo

Arezzo
10.0 out of 10, Exceptional, (18)
"Amazing location, great pool, ideal for a large group. Very friendly and helpful hosts. Second stay at this property would definitely consider it again. "
United Kingdom
Julie C.
The price is €2,402
includes taxes & fees
7 Dec - 8 Dec
Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo

Villa in Toscana - Reggello con Piscina, Wi-Fi, Giardini.

Reggello
10.0 out of 10, Exceptional, (48)
"Eduardo’s property was perfect for our family of 5’s stay for 4 days in the Tuscany region. We had access to the entire compound, including olive tree grove, grape vines, and countless other vegetation. The pool was cleanly and a great amenity for our use during our stay. For our stay, it was the ideal setup for space, amenities, and cost.The town is located approximately 45 minutes to Florence, hour to Siena and surrounding vineyards, and 5-10 minutes from the local town. We would recommend...
United States
Drew M.
Villa in Toscana - Reggello con Piscina, Wi-Fi, Giardini.

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 €119
includes taxes & fees
29 Nov - 30 Nov
Casa Vacanze Squarcialupi
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Penna Hotel Reviews

Find out more about Penna

Everything you need to know about Penna holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Penna holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Penna holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Penna holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Penna holiday rentals we have selected for you start as low as €94 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Penna rentals

At Expedia, we put the best Penna holiday 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 holiday.

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 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.